Greensboro/High Point to Chicago (ORD) flights from $295 round trip, Nov 2026–Feb 2027

Axel-exclusive from $295 round trip (Sat Nov 14–Mon Nov 16, 2026, American 1 stop), published Oct 29, 2026; one-way from $155 (Sat Nov 14, American 1 stop). 90 departure dates priced, one adult, economy.

Compare flight prices from Greensboro/High Point to Chicago for your dates. There are no recent complete one-adult round trips here to set a price target.

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Greensboro/High Point to Chicago flight prices at a glance

• One-way: from $155 (American, 1 stop) on Sat, Nov 14, 2026; one-way totals sit beside each departure in the calendar.
• Cheapest day to leave: Saturday departures had the lowest published round trips (median $295); Friday the highest (median $305).

Greensboro/High Point to Chicago flight prices on popular dates

Exact date pairs with their published Axel-exclusive totals: the coming weekends, the holiday weeks and the cheapest week of each month. One adult, economy, USD, including required taxes. Open a pair for its flights; the full calendar below has every priced date.

Greensboro/High Point to Chicago one-way flight prices

Cheapest one-way: $155 on Sat, Nov 14, 2026, American, 1 stop. One-way totals run $155 to $222.75 across 90 departure dates; each departure in the calendar below lists its one-way price beside the round trips. Published Oct 29, 2026.

Greensboro/High Point to Chicago round trip flight prices and average fare

Published round trips start at $295 and run to $389.13 for the lowest fare on each of 90 departure dates; the median lowest round trip is $305, and 58 of the 90 dates have a round trip at $305 or less. One adult, economy, Axel-exclusive totals including required taxes. Published Oct 29, 2026.

Cheapest day of week and month to fly Greensboro/High Point to Chicago

Cheapest month by published price: January 2027, where the lowest round trip per departure date has a median of $305; dearest: November 2026 at $360.13. Cheapest day of the week to leave: Saturday (median lowest round trip $295); dearest: Friday ($305). Published Oct 29, 2026.

Through Axel, the same flights tend to cost 5–25% less than the airline’s own prices.

Greensboro/High Point (GSO) to Chicago (ORD): round-trip and one-way prices for 90 departure dates, Nov 14, 2026–Feb 11, 2027. One adult, economy. Open a departure for return options; use the chooser below for other travelers and cabins.

American, out: 1 stop via CLT, back: 1 stop via CLT, from $295 round trip · American, nonstop, from $315 round trip

Saved nonstop flight times: 2h 36m outbound; 2h 2m returning.

How to read the calendar: published Axel-exclusive USD totals for one adult, including required taxes; basic economy may apply. Each return range includes its own prices. Only the listed dates and options are priced. Date links open published details; live search checks availability and lets you select flights.

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

Greensboro/High Point to Chicago flight prices by month

November 2026: Nov 14 from $295 · Nov 15–19 from $305 · Nov 20 from $360.13 · Nov 21 from $346.63 · Nov 22–27 from $360.13 · Nov 28 from $346.63 · Nov 29–30 from $360.13.

December 2026: Dec 1–4 from $305 · Dec 5 from $295 · Dec 6–11 from $305 · Dec 12 from $295 · Dec 13–14 from $305 · Dec 15–16 from $315 · Dec 17 from $341.88 · Dec 18 from $389.13 · Dec 19 from $376.13 · Dec 20–21 from $389.13 · Dec 22–25 from $352.25 · Dec 26 from $339.25 · Dec 27 from $352.25 · Dec 28–31 from $344.38.

January 2027: Jan 1 from $344.38 · Jan 2 from $331.88 · Jan 3–4 from $344.38 · Jan 5–8 from $305 · Jan 9 from $295 · Jan 10–15 from $305 · Jan 16 from $295 · Jan 17–22 from $305 · Jan 23 from $295 · Jan 24–29 from $305 · Jan 30 from $295 · Jan 31 from $305.

February 2027: Feb 1–5 from $305 · Feb 6 from $295 · Feb 7–11 from $305.

Month summaries show the lowest displayed round-trip total for each departure. Match your return date to the calendar below.

Greensboro/High Point to Chicago flights in November 2026: price by departure date

GSO → ORD · USD · 1 adult · economy · published Oct 29, 2026

Sat, Nov 14, 2026 · round trip · return Nov 15: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Nov 16: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Nov 17: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Nov 18–19: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Nov 20–21: American $360.13, out: 1 stop via CLT, back: nonstop / United $368.38, out: nonstop, back: 1 stop via IAD; return Nov 22: American $360.13, out: 1 stop via CLT, back: nonstop / United $381.88, nonstop; return Nov 23: American $346.63, out: 1 stop via CLT, back: 1 stop via CLT / United $381.88, nonstop; return Nov 24: American $346.63, out: 1 stop via CLT, back: 1 stop via DCA / United $381.88, nonstop; return Nov 25–26: American $360.13, out: 1 stop via CLT, back: nonstop / United $381.88, nonstop; return Nov 27–28: American $360.13, out: 1 stop via CLT, back: nonstop / United $368.38, out: nonstop, back: 1 stop via IAD · one-way: American $155, out: 1 stop via CLT
Hotels in Chicago for these nights (Nov 14–16, 2026 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $312 total · 4★ Freehand Chicago, $173 total · 5★ Sofitel Chicago Magnificent Mile, $626 total

Sun, Nov 15, 2026 · round trip · return Nov 16: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Nov 17: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Nov 18–19: American $315 / United $325, nonstop; return Nov 20–21: United $368.38, out: nonstop, back: 1 stop via IAD / American $370.13, nonstop; return Nov 22: American $370.13 / United $381.88, nonstop; return Nov 23: American $356.63, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Nov 24: American $356.63, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Nov 25–26: American $370.13 / United $381.88, nonstop; return Nov 27–28: United $368.38, out: nonstop, back: 1 stop via IAD / American $370.13, nonstop; return Nov 29: American $370.13 / United $381.88, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Nov 15–16, 2026 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $114 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $33 total · 5★ Sofitel Chicago Magnificent Mile, $319 total

Mon, Nov 16, 2026 · round trip · return Nov 17: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Nov 18–19: American $315 / United $325, nonstop; return Nov 20–21: United $368.38, out: nonstop, back: 1 stop via IAD / American $370.13, nonstop; return Nov 22: American $370.13 / United $381.88, nonstop; return Nov 23: American $356.63, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Nov 24: American $356.63, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Nov 25–26: American $370.13 / United $381.88, nonstop; return Nov 27–28: United $368.38, out: nonstop, back: 1 stop via IAD / American $370.13, nonstop; return Nov 29: American $370.13 / United $381.88, nonstop; return Nov 30: American $356.63, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Nov 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $110 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $33 total · 5★ Sofitel Chicago Magnificent Mile, $446 total

Tue, Nov 17, 2026 · round trip · return Nov 18–19: American $315 / United $325, nonstop; return Nov 20–21: United $368.38, out: nonstop, back: 1 stop via IAD / American $370.13, nonstop; return Nov 22: American $370.13 / United $381.88, nonstop; return Nov 23: American $356.63, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Nov 24: American $356.63, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Nov 25–26: American $370.13 / United $381.88, nonstop; return Nov 27–28: United $368.38, out: nonstop, back: 1 stop via IAD / American $370.13, nonstop; return Nov 29: American $370.13 / United $381.88, nonstop; return Nov 30: American $356.63, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Dec 1: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Nov 17 – Dec 1, 2026 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,807 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $858 total · 5★ Sofitel Chicago Magnificent Mile, $5,126 total

Wed, Nov 18, 2026 · round trip · return Nov 19: American $315 / United $325, nonstop; return Nov 20–21: United $368.38, out: nonstop, back: 1 stop via IAD / American $370.13, nonstop; return Nov 22: American $370.13 / United $381.88, nonstop; return Nov 23: American $356.63, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Nov 24: American $356.63, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Nov 25–26: American $370.13 / United $381.88, nonstop; return Nov 27–28: United $368.38, out: nonstop, back: 1 stop via IAD / American $370.13, nonstop; return Nov 29: American $370.13 / United $381.88, nonstop; return Nov 30: American $356.63, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Dec 1: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 2: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Nov 18 – Dec 1, 2026 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,699 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $808 total · 5★ Sofitel Chicago Magnificent Mile, $4,614 total

Thu, Nov 19, 2026 · round trip · return Nov 20–21: United $368.38, out: nonstop, back: 1 stop via IAD / American $370.13, nonstop; return Nov 22: American $370.13 / United $381.88, nonstop; return Nov 23: American $356.63, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Nov 24: American $356.63, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Nov 25–26: American $370.13 / United $381.88, nonstop; return Nov 27–28: United $368.38, out: nonstop, back: 1 stop via IAD / American $370.13, nonstop; return Nov 29: American $370.13 / United $381.88, nonstop; return Nov 30: American $356.63, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Dec 1: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 2–3: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Nov 19 – Dec 1, 2026 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,591 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $758 total · 5★ Sofitel Chicago Magnificent Mile, $4,307 total

Fri, Nov 20, 2026 · round trip · return Nov 21: United $425.26, out: nonstop, back: 1 stop via IAD / American $425.26, nonstop; return Nov 22: American $425.26 / United $438.76, nonstop; return Nov 23: American $411.76, out: nonstop, back: 1 stop via CLT / United $438.76, nonstop; return Nov 24: American $411.76, out: nonstop, back: 1 stop via DCA / United $438.76, nonstop; return Nov 25–26: American $425.26 / United $438.76, nonstop; return Nov 27: American $425.26, nonstop / United $425.26, out: nonstop, back: 1 stop via IAD; return Nov 28: United $425.26, out: nonstop, back: 1 stop via IAD / American $425.26, nonstop; return Nov 29: American $425.26 / United $438.76, nonstop; return Nov 30: American $411.76, out: nonstop, back: 1 stop via CLT / United $438.76, nonstop; return Dec 1: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $370.13 / United $381.88, nonstop; return Dec 4: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD · one-way: American $222.75, nonstop
Hotels in Chicago for these nights (Nov 20 – Dec 1, 2026 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,507 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $739 total · 5★ Sofitel Chicago Magnificent Mile, $4,004 total

Sat, Nov 21, 2026 · round trip · return Nov 22: American $411.76, out: 1 stop via CLT, back: nonstop / United $438.76, nonstop; return Nov 23: American $398.26, out: 1 stop via CLT, back: 1 stop via CLT / United $438.76, nonstop; return Nov 24: American $398.26, out: 1 stop via CLT, back: 1 stop via DCA / United $438.76, nonstop; return Nov 25–26: American $411.76, out: 1 stop via CLT, back: nonstop / United $438.76, nonstop; return Nov 27–28: American $411.76, out: 1 stop via CLT, back: nonstop / United $425.26, out: nonstop, back: 1 stop via IAD; return Nov 29: American $411.76, out: 1 stop via CLT, back: nonstop / United $438.76, nonstop; return Nov 30: American $398.26, out: 1 stop via CLT, back: 1 stop via CLT / United $438.76, nonstop; return Dec 1: American $346.63, out: 1 stop via CLT, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $356.63, out: 1 stop via CLT, back: nonstop / United $381.88, nonstop; return Dec 4–5: American $356.63, out: 1 stop via CLT, back: nonstop / United $371.88, out: nonstop, back: 1 stop via IAD · one-way: American $209.25, out: 1 stop via CLT
Hotels in Chicago for these nights (Nov 21 – Dec 1, 2026 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,309 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $653 total · 5★ Nobu Hotel Chicago, $3,628 total

Sun, Nov 22, 2026 · round trip · return Nov 23: American $411.76, out: nonstop, back: 1 stop via CLT / United $438.76, nonstop; return Nov 24: American $411.76, out: nonstop, back: 1 stop via DCA / United $438.76, nonstop; return Nov 25–26: American $425.26 / United $438.76, nonstop; return Nov 27: American $425.26, nonstop / United $425.26, out: nonstop, back: 1 stop via IAD; return Nov 28: United $425.26, out: nonstop, back: 1 stop via IAD / American $425.26, nonstop; return Nov 29: American $425.26 / United $438.76, nonstop; return Nov 30: American $411.76, out: nonstop, back: 1 stop via CLT / United $438.76, nonstop; return Dec 1: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $370.13 / United $381.88, nonstop; return Dec 4–5: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 6: American $370.13 / United $381.88, nonstop · one-way: American $222.75, nonstop
Hotels in Chicago for these nights (Nov 22 – Dec 1, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,111 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $552 total · 5★ Sofitel Chicago Magnificent Mile, $2,303 total

Mon, Nov 23, 2026 · round trip · return Nov 24: American $411.76, out: nonstop, back: 1 stop via DCA / United $438.76, nonstop; return Nov 25–26: American $425.26 / United $438.76, nonstop; return Nov 27–28: United $425.26, out: nonstop, back: 1 stop via IAD / American $425.26, nonstop; return Nov 29: American $425.26 / United $438.76, nonstop; return Nov 30: American $411.76, out: nonstop, back: 1 stop via CLT / United $438.76, nonstop; return Dec 1: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $370.13 / United $381.88, nonstop; return Dec 4–5: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 6: American $370.13 / United $381.88, nonstop; return Dec 7: American $360.13, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop · one-way: American $222.75, nonstop
Hotels in Chicago for these nights (Nov 23 – Dec 1, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,002 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $533 total · 5★ Sofitel Chicago Magnificent Mile, $2,097 total

Tue, Nov 24, 2026 · round trip · return Nov 25–26: American $425.26 / United $438.76, nonstop; return Nov 27: American $425.26, nonstop / United $425.26, out: nonstop, back: 1 stop via IAD; return Nov 28: United $425.26, out: nonstop, back: 1 stop via IAD / American $425.26, nonstop; return Nov 29: American $425.26 / United $438.76, nonstop; return Nov 30: American $411.76, out: nonstop, back: 1 stop via CLT / United $438.76, nonstop; return Dec 1: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $370.13 / United $381.88, nonstop; return Dec 4–5: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 6: American $370.13 / United $381.88, nonstop; return Dec 7: American $360.13, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Dec 8: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop · one-way: American $222.75, nonstop
Hotels in Chicago for these nights (Nov 24 – Dec 1, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $893 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $514 total · 5★ Sofitel Chicago Magnificent Mile, $1,876 total

Wed, Nov 25, 2026 · round trip · return Nov 26: American $425.26 / United $438.76, nonstop; return Nov 27: American $425.26, nonstop / United $425.26, out: nonstop, back: 1 stop via IAD; return Nov 28: United $425.26, out: nonstop, back: 1 stop via IAD / American $425.26, nonstop; return Nov 29: American $425.26 / United $438.76, nonstop; return Nov 30: American $411.76, out: nonstop, back: 1 stop via CLT / United $438.76, nonstop; return Dec 1: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $370.13 / United $381.88, nonstop; return Dec 4–5: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 6: American $370.13 / United $381.88, nonstop; return Dec 7: American $360.13, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Dec 8: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 9: American $370.13 / United $381.88, nonstop · one-way: American $222.75, nonstop
Hotels in Chicago for these nights (Nov 25 – Dec 1, 2026 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $784 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $495 total · 5★ Sofitel Chicago Magnificent Mile, $1,659 total

Thu, Nov 26, 2026 · round trip · return Nov 27–28: United $425.26, out: nonstop, back: 1 stop via IAD / American $425.26, nonstop; return Nov 29: American $425.26 / United $438.76, nonstop; return Nov 30: American $411.76, out: nonstop, back: 1 stop via CLT / United $438.76, nonstop; return Dec 1: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $370.13 / United $381.88, nonstop; return Dec 4–5: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 6: American $370.13 / United $381.88, nonstop; return Dec 7: American $360.13, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Dec 8: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 9–10: American $370.13 / United $381.88, nonstop · one-way: American $222.75, nonstop
Hotels in Chicago for these nights (Nov 26 – Dec 1, 2026 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $675 total · 4★ Freehand Chicago, $430 total · 5★ Sofitel Chicago Magnificent Mile, $1,434 total

Fri, Nov 27, 2026 · round trip · return Nov 28: United $425.26, out: nonstop, back: 1 stop via IAD / American $425.26, nonstop; return Nov 29: American $425.26 / United $438.76, nonstop; return Nov 30: American $411.76, out: nonstop, back: 1 stop via CLT / United $438.76, nonstop; return Dec 1: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $370.13 / United $381.88, nonstop; return Dec 4–5: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 6: American $370.13 / United $381.88, nonstop; return Dec 7: American $360.13, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Dec 8: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 9–10: American $370.13 / United $381.88, nonstop; return Dec 11: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD · one-way: American $222.75, nonstop
Hotels in Chicago for these nights (Nov 27 – Dec 1, 2026 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $538 total · 4★ Freehand Chicago, $344 total · 5★ Sofitel Chicago Magnificent Mile, $1,220 total

Sat, Nov 28, 2026 · round trip · return Nov 29: American $411.76, out: 1 stop via CLT, back: nonstop / United $438.76, nonstop; return Nov 30: American $398.26, out: 1 stop via CLT, back: 1 stop via CLT / United $438.76, nonstop; return Dec 1: American $346.63, out: 1 stop via CLT, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $356.63, out: 1 stop via CLT, back: nonstop / United $381.88, nonstop; return Dec 4–5: American $356.63, out: 1 stop via CLT, back: nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 6: American $356.63, out: 1 stop via CLT, back: nonstop / United $381.88, nonstop; return Dec 7: American $346.63, out: 1 stop via CLT, back: 1 stop via CLT / United $381.88, nonstop; return Dec 8: American $346.63, out: 1 stop via CLT, back: 1 stop via DCA / United $381.88, nonstop; return Dec 9–10: American $356.63, out: 1 stop via CLT, back: nonstop / United $381.88, nonstop; return Dec 11–12: American $356.63, out: 1 stop via CLT, back: nonstop / United $371.88, out: nonstop, back: 1 stop via IAD · one-way: American $209.25, out: 1 stop via CLT
Hotels in Chicago for these nights (Nov 28 – Dec 1, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $334 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $258 total · 5★ Sofitel Chicago Magnificent Mile, $912 total

Sun, Nov 29, 2026 · round trip · return Nov 30: American $411.76, out: nonstop, back: 1 stop via CLT / United $438.76, nonstop; return Dec 1: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $370.13 / United $381.88, nonstop; return Dec 4–5: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 6: American $370.13 / United $381.88, nonstop; return Dec 7: American $360.13, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Dec 8: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 9–10: American $370.13 / United $381.88, nonstop; return Dec 11–12: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 13: American $370.13 / United $381.88, nonstop · one-way: American $222.75, nonstop
Hotels in Chicago for these nights (Nov 29 – Dec 1, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $178 total · 4★ Freehand Chicago, $172 total · 5★ Sofitel Chicago Magnificent Mile, $610 total

Mon, Nov 30, 2026 · round trip · return Dec 1: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 2–3: American $370.13 / United $381.88, nonstop; return Dec 4–5: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 6: American $370.13 / United $381.88, nonstop; return Dec 7: American $360.13, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop; return Dec 8: American $360.13, out: nonstop, back: 1 stop via DCA / United $381.88, nonstop; return Dec 9–10: American $370.13 / United $381.88, nonstop; return Dec 11–12: American $370.13, nonstop / United $371.88, out: nonstop, back: 1 stop via IAD; return Dec 13: American $370.13 / United $381.88, nonstop; return Dec 14: American $360.13, out: nonstop, back: 1 stop via CLT / United $381.88, nonstop · one-way: American $222.75, nonstop
Hotels in Chicago for these nights (Nov 30 – Dec 1, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $92 total · 4★ Freehand Chicago, $85 total · 5★ Sofitel Chicago Magnificent Mile, $302 total

Greensboro/High Point to Chicago flights in December 2026: price by departure date

GSO → ORD · USD · 1 adult · economy · published Oct 29, 2026

Tue, Dec 1, 2026 · round trip · return Dec 2–3: American $315 / United $325, nonstop; return Dec 4: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Dec 5: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 6: American $315 / United $325, nonstop; return Dec 7: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 8: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 9–10: American $315 / United $325, nonstop; return Dec 11–12: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 13: American $315 / United $325, nonstop; return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 1–7, 2026 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $792 total · 4★ Freehand Chicago, $481 total · 5★ Sofitel Chicago Magnificent Mile, $1,684 total

Wed, Dec 2, 2026 · round trip · return Dec 3: American $315 / United $325, nonstop; return Dec 4: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 5: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Dec 6: American $315 / United $325, nonstop; return Dec 7: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 8: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 9–10: American $315 / United $325, nonstop; return Dec 11–12: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 13: American $315 / United $325, nonstop; return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 2–7, 2026 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $652 total · 4★ Freehand Chicago, $395 total · 5★ Sofitel Chicago Magnificent Mile, $1,381 total

Thu, Dec 3, 2026 · round trip · return Dec 4: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 5: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Dec 6: American $315 / United $325, nonstop; return Dec 7: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 8: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 9–10: American $315 / United $325, nonstop; return Dec 11–12: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 13: American $315 / United $325, nonstop; return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 3–7, 2026 · 4 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $482 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $310 total · 5★ Sofitel Chicago Magnificent Mile, $1,079 total

Fri, Dec 4, 2026 · round trip · return Dec 5: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Dec 6: American $315 / United $325, nonstop; return Dec 7: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 8: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 9–10: American $315 / United $325, nonstop; return Dec 11: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 12: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Dec 13: American $315 / United $325, nonstop; return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $315 / United $325, nonstop; return Dec 18: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $345 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $220 total · 5★ Sofitel Chicago Magnificent Mile, $841 total

Sat, Dec 5, 2026 · round trip · return Dec 6: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Dec 7: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Dec 8: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Dec 9–10: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Dec 11–12: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Dec 13: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Dec 14: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Dec 18–19: American $352.25, out: 1 stop via CLT, back: nonstop / United $360.75, out: nonstop, back: 1 stop via IAD · one-way: American $155, out: 1 stop via CLT
Hotels in Chicago for these nights (Dec 5–7, 2026 · 2 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $229 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $84 total · 5★ Sofitel Chicago Magnificent Mile, $539 total

Sun, Dec 6, 2026 · round trip · return Dec 7: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 8: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 9–10: American $315 / United $325, nonstop; return Dec 11–12: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 13: American $315 / United $325, nonstop; return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $315 / United $325, nonstop; return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 6–7, 2026 · 1 night · 2 adults, 1 room): 3★ The Willows Hotel, $97 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $231 total

Mon, Dec 7, 2026 · round trip · return Dec 8: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 9–10: American $315 / United $325, nonstop; return Dec 11–12: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Dec 13: American $315 / United $325, nonstop; return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $315 / United $325, nonstop; return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop; return Dec 21: American $349.25, out: nonstop, back: 1 stop via CLT / United $373.75, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 7–8, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $207 total

Tue, Dec 8, 2026 · round trip · return Dec 9–10: American $315 / United $325, nonstop; return Dec 11: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 12: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Dec 13: American $315 / United $325, nonstop; return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $315 / United $325, nonstop; return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop; return Dec 21: American $349.25, out: nonstop, back: 1 stop via CLT / United $373.75, nonstop; return Dec 22: American $349.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 8–14, 2026 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Wed, Dec 9, 2026 · round trip · return Dec 10: American $315 / United $325, nonstop; return Dec 11: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 12: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Dec 13: American $315 / United $325, nonstop; return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $315 / United $325, nonstop; return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop; return Dec 21: American $349.25, out: nonstop, back: 1 stop via CLT / United $373.75, nonstop; return Dec 22: American $349.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Dec 23: American $362.25 / United $373.75, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 9–14, 2026 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Thu, Dec 10, 2026 · round trip · return Dec 11–12: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 13: American $315 / United $325, nonstop; return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $315 / United $325, nonstop; return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop; return Dec 21: American $349.25, out: nonstop, back: 1 stop via CLT / United $373.75, nonstop; return Dec 22: American $349.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Dec 23–24: American $362.25 / United $373.75, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 10–14, 2026 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Fri, Dec 11, 2026 · round trip · return Dec 12: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Dec 13: American $315 / United $325, nonstop; return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $315 / United $325, nonstop; return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop; return Dec 21: American $349.25, out: nonstop, back: 1 stop via CLT / United $373.75, nonstop; return Dec 22: American $349.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Dec 23–24: American $362.25 / United $373.75, nonstop; return Dec 25: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sat, Dec 12, 2026 · round trip · return Dec 13: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Dec 14: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Dec 18–19: American $352.25, out: 1 stop via CLT, back: nonstop / United $360.75, out: nonstop, back: 1 stop via IAD; return Dec 20: American $352.25, out: 1 stop via CLT, back: nonstop / United $373.75, nonstop; return Dec 21: American $339.25, out: 1 stop via CLT, back: 1 stop via CLT / United $373.75, nonstop; return Dec 22: American $339.25, out: 1 stop via CLT, back: 1 stop via DCA / United $373.75, nonstop; return Dec 23–24: American $352.25, out: 1 stop via CLT, back: nonstop / United $373.75, nonstop; return Dec 25–26: American $352.25, out: 1 stop via CLT, back: nonstop / United $360.75, out: nonstop, back: 1 stop via IAD · one-way: American $155, out: 1 stop via CLT
Hotels in Chicago for these nights (Dec 12–14, 2026 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sun, Dec 13, 2026 · round trip · return Dec 14: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $315 / United $325, nonstop; return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop; return Dec 21: American $349.25, out: nonstop, back: 1 stop via CLT / United $373.75, nonstop; return Dec 22: American $349.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Dec 23–24: American $362.25 / United $373.75, nonstop; return Dec 25–26: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 27: American $362.25 / United $373.75, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 13–14, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Mon, Dec 14, 2026 · round trip · return Dec 15: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Dec 16–17: American $315 / United $325, nonstop; return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop; return Dec 21: American $349.25, out: nonstop, back: 1 stop via CLT / United $373.75, nonstop; return Dec 22: American $349.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Dec 23–24: American $362.25 / United $373.75, nonstop; return Dec 25–26: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 27: American $362.25 / United $373.75, nonstop; return Dec 28: American $341.88, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 14–15, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Tue, Dec 15, 2026 · round trip · return Dec 16–17: American $315 / United $325, nonstop; return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop; return Dec 21: American $349.25, out: nonstop, back: 1 stop via CLT / United $373.75, nonstop; return Dec 22: American $349.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Dec 23–24: American $362.25 / United $373.75, nonstop; return Dec 25–26: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 27: American $362.25 / United $373.75, nonstop; return Dec 28: American $341.88, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop; return Dec 29: American $341.88, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 15–16, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Wed, Dec 16, 2026 · round trip · return Dec 17: American $315 / United $325, nonstop; return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop; return Dec 21: American $349.25, out: nonstop, back: 1 stop via CLT / United $373.75, nonstop; return Dec 22: American $349.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Dec 23–24: American $362.25 / United $373.75, nonstop; return Dec 25–26: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 27: American $362.25 / United $373.75, nonstop; return Dec 28: American $341.88, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop; return Dec 29: American $341.88, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Dec 30: American $354.38 / United $365.63, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Thu, Dec 17, 2026 · round trip · return Dec 18–19: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 20: American $362.25 / United $373.75, nonstop; return Dec 21: American $349.25, out: nonstop, back: 1 stop via CLT / United $373.75, nonstop; return Dec 22: American $349.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Dec 23–24: American $362.25 / United $373.75, nonstop; return Dec 25–26: United $360.75, out: nonstop, back: 1 stop via IAD / American $362.25, nonstop; return Dec 27: American $362.25 / United $373.75, nonstop; return Dec 28: American $341.88, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop; return Dec 29: American $341.88, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Dec 30–31: American $354.38 / United $365.63, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Dec 17–28, 2026 · 11 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Fri, Dec 18, 2026 · round trip · return Dec 19: American $409.50, nonstop / United $409.50, out: nonstop, back: 1 stop via IAD; return Dec 20: American $409.50 / United $422.50, nonstop; return Dec 21: American $396.50, out: nonstop, back: 1 stop via CLT / United $422.50, nonstop; return Dec 22: American $396.50, out: nonstop, back: 1 stop via DCA / United $422.50, nonstop; return Dec 23–24: American $409.50 / United $422.50, nonstop; return Dec 25: United $409.50, out: nonstop, back: 1 stop via IAD / American $409.50, nonstop; return Dec 26: American $409.50, nonstop / United $409.50, out: nonstop, back: 1 stop via IAD; return Dec 27: American $409.50 / United $422.50, nonstop; return Dec 28: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Dec 29: American $389.13, out: nonstop, back: 1 stop via DCA / United $414.38, nonstop; return Dec 30–31: American $401.63 / United $414.38, nonstop; return Jan 1, 2027: American $401.63, nonstop / United $401.88, out: nonstop, back: 1 stop via IAD · one-way: American $214.50, nonstop
Hotels in Chicago for these nights (Dec 18–28, 2026 · 10 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sat, Dec 19, 2026 · round trip · return Dec 20: American $396.50, out: 1 stop via CLT, back: nonstop / United $422.50, nonstop; return Dec 21: American $383.50, out: 1 stop via CLT, back: 1 stop via CLT / United $422.50, nonstop; return Dec 22: American $383.50, out: 1 stop via CLT, back: 1 stop via DCA / United $422.50, nonstop; return Dec 23–24: American $396.50, out: 1 stop via CLT, back: nonstop / United $422.50, nonstop; return Dec 25–26: American $396.50, out: 1 stop via CLT, back: nonstop / United $409.50, out: nonstop, back: 1 stop via IAD; return Dec 27: American $396.50, out: 1 stop via CLT, back: nonstop / United $422.50, nonstop; return Dec 28: American $376.13, out: 1 stop via CLT, back: 1 stop via CLT / United $414.38, nonstop; return Dec 29: American $376.13, out: 1 stop via CLT, back: 1 stop via DCA / United $414.38, nonstop; return Dec 30–31: American $388.63, out: 1 stop via CLT, back: nonstop / United $414.38, nonstop; return Jan 1–2, 2027: American $388.63, out: 1 stop via CLT, back: nonstop / United $401.88, out: nonstop, back: 1 stop via IAD · one-way: American $201.50, out: 1 stop via CLT
Hotels in Chicago for these nights (Dec 19–28, 2026 · 9 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sun, Dec 20, 2026 · round trip · return Dec 21: American $396.50, out: nonstop, back: 1 stop via CLT / United $422.50, nonstop; return Dec 22: American $396.50, out: nonstop, back: 1 stop via DCA / United $422.50, nonstop; return Dec 23–24: American $409.50 / United $422.50, nonstop; return Dec 25–26: American $409.50, nonstop / United $409.50, out: nonstop, back: 1 stop via IAD; return Dec 27: American $409.50 / United $422.50, nonstop; return Dec 28: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Dec 29: American $389.13, out: nonstop, back: 1 stop via DCA / United $414.38, nonstop; return Dec 30–31: American $401.63 / United $414.38, nonstop; return Jan 1–2, 2027: American $401.63, nonstop / United $401.88, out: nonstop, back: 1 stop via IAD; return Jan 3, 2027: American $401.63 / United $414.38, nonstop · one-way: American $214.50, nonstop
Hotels in Chicago for these nights (Dec 20–28, 2026 · 8 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Mon, Dec 21, 2026 · round trip · return Dec 22: American $396.50, out: nonstop, back: 1 stop via DCA / United $422.50, nonstop; return Dec 23–24: American $409.50 / United $422.50, nonstop; return Dec 25: United $409.50, out: nonstop, back: 1 stop via IAD / American $409.50, nonstop; return Dec 26: American $409.50, nonstop / United $409.50, out: nonstop, back: 1 stop via IAD; return Dec 27: American $409.50 / United $422.50, nonstop; return Dec 28: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Dec 29: American $389.13, out: nonstop, back: 1 stop via DCA / United $414.38, nonstop; return Dec 30–31: American $401.63 / United $414.38, nonstop; return Jan 1–2, 2027: American $401.63, nonstop / United $401.88, out: nonstop, back: 1 stop via IAD; return Jan 3, 2027: American $401.63 / United $414.38, nonstop; return Jan 4, 2027: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop · one-way: American $214.50, nonstop
Hotels in Chicago for these nights (Dec 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Tue, Dec 22, 2026 · round trip · return Dec 23–24: American $409.50 / United $422.50, nonstop; return Dec 25: United $409.50, out: nonstop, back: 1 stop via IAD / American $409.50, nonstop; return Dec 26: American $409.50, nonstop / United $409.50, out: nonstop, back: 1 stop via IAD; return Dec 27: American $409.50 / United $422.50, nonstop; return Dec 28: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Dec 29: American $389.13, out: nonstop, back: 1 stop via DCA / United $414.38, nonstop; return Dec 30–31: American $401.63 / United $414.38, nonstop; return Jan 1–2, 2027: American $401.63, nonstop / United $401.88, out: nonstop, back: 1 stop via IAD; return Jan 3, 2027: American $401.63 / United $414.38, nonstop; return Jan 4, 2027: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Jan 5, 2027: American $352.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop · one-way: American $214.50, nonstop
Hotels in Chicago for these nights (Dec 22 – Jan 5, 2027 · 14 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Wed, Dec 23, 2026 · round trip · return Dec 24: American $409.50 / United $422.50, nonstop; return Dec 25–26: American $409.50, nonstop / United $409.50, out: nonstop, back: 1 stop via IAD; return Dec 27: American $409.50 / United $422.50, nonstop; return Dec 28: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Dec 29: American $389.13, out: nonstop, back: 1 stop via DCA / United $414.38, nonstop; return Dec 30–31: American $401.63 / United $414.38, nonstop; return Jan 1–2, 2027: American $401.63, nonstop / United $401.88, out: nonstop, back: 1 stop via IAD; return Jan 3, 2027: American $401.63 / United $414.38, nonstop; return Jan 4, 2027: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Jan 5, 2027: American $352.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Jan 6, 2027: American $362.25 / United $373.75, nonstop · one-way: American $214.50, nonstop
Hotels in Chicago for these nights (Dec 23 – Jan 5, 2027 · 13 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Thu, Dec 24, 2026 · round trip · return Dec 25: United $409.50, out: nonstop, back: 1 stop via IAD / American $409.50, nonstop; return Dec 26: American $409.50, nonstop / United $409.50, out: nonstop, back: 1 stop via IAD; return Dec 27: American $409.50 / United $422.50, nonstop; return Dec 28: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Dec 29: American $389.13, out: nonstop, back: 1 stop via DCA / United $414.38, nonstop; return Dec 30–31: American $401.63 / United $414.38, nonstop; return Jan 1–2, 2027: American $401.63, nonstop / United $401.88, out: nonstop, back: 1 stop via IAD; return Jan 3, 2027: American $401.63 / United $414.38, nonstop; return Jan 4, 2027: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Jan 5, 2027: American $352.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Jan 6–7, 2027: American $362.25 / United $373.75, nonstop · one-way: American $214.50, nonstop
Hotels in Chicago for these nights (Dec 24 – Jan 5, 2027 · 12 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Fri, Dec 25, 2026 · round trip · return Dec 26: United $409.50, out: nonstop, back: 1 stop via IAD / American $409.50, nonstop; return Dec 27: American $409.50 / United $422.50, nonstop; return Dec 28: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Dec 29: American $389.13, out: nonstop, back: 1 stop via DCA / United $414.38, nonstop; return Dec 30–31: American $401.63 / United $414.38, nonstop; return Jan 1–2, 2027: American $401.63, nonstop / United $401.88, out: nonstop, back: 1 stop via IAD; return Jan 3, 2027: American $401.63 / United $414.38, nonstop; return Jan 4, 2027: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Jan 5, 2027: American $352.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Jan 6–7, 2027: American $362.25 / United $373.75, nonstop; return Jan 8, 2027: American $362.25, nonstop / United $363.75, out: nonstop, back: 1 stop via IAD · one-way: American $214.50, nonstop
Hotels in Chicago for these nights (Dec 25 – Jan 5, 2027 · 11 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sat, Dec 26, 2026 · round trip · return Dec 27: American $396.50, out: 1 stop via CLT, back: nonstop / United $422.50, nonstop; return Dec 28: American $376.13, out: 1 stop via CLT, back: 1 stop via CLT / United $414.38, nonstop; return Dec 29: American $376.13, out: 1 stop via CLT, back: 1 stop via DCA / United $414.38, nonstop; return Dec 30–31: American $388.63, out: 1 stop via CLT, back: nonstop / United $414.38, nonstop; return Jan 1–2, 2027: American $388.63, out: 1 stop via CLT, back: nonstop / United $401.88, out: nonstop, back: 1 stop via IAD; return Jan 3, 2027: American $388.63, out: 1 stop via CLT, back: nonstop / United $414.38, nonstop; return Jan 4, 2027: American $376.13, out: 1 stop via CLT, back: 1 stop via CLT / United $414.38, nonstop; return Jan 5, 2027: American $339.25, out: 1 stop via CLT, back: 1 stop via DCA / United $373.75, nonstop; return Jan 6–7, 2027: American $349.25, out: 1 stop via CLT, back: nonstop / United $373.75, nonstop; return Jan 8–9, 2027: American $349.25, out: 1 stop via CLT, back: nonstop / United $363.75, out: nonstop, back: 1 stop via IAD · one-way: American $201.50, out: 1 stop via CLT
Hotels in Chicago for these nights (Dec 26 – Jan 5, 2027 · 10 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sun, Dec 27, 2026 · round trip · return Dec 28: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Dec 29: American $389.13, out: nonstop, back: 1 stop via DCA / United $414.38, nonstop; return Dec 30–31: American $401.63 / United $414.38, nonstop; return Jan 1–2, 2027: American $401.63, nonstop / United $401.88, out: nonstop, back: 1 stop via IAD; return Jan 3, 2027: American $401.63 / United $414.38, nonstop; return Jan 4, 2027: American $389.13, out: nonstop, back: 1 stop via CLT / United $414.38, nonstop; return Jan 5, 2027: American $352.25, out: nonstop, back: 1 stop via DCA / United $373.75, nonstop; return Jan 6–7, 2027: American $362.25 / United $373.75, nonstop; return Jan 8–9, 2027: American $362.25, nonstop / United $363.75, out: nonstop, back: 1 stop via IAD; return Jan 10, 2027: American $362.25 / United $373.75, nonstop · one-way: American $214.50, nonstop
Hotels in Chicago for these nights (Dec 27 – Jan 5, 2027 · 9 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Mon, Dec 28, 2026 · round trip · return Dec 29: American $381.26, out: nonstop, back: 1 stop via DCA / United $406.26, nonstop; return Dec 30–31: American $393.76 / United $406.26, nonstop; return Jan 1, 2027: United $393.76, out: nonstop, back: 1 stop via IAD / American $393.76, nonstop; return Jan 2, 2027: American $393.76, nonstop / United $393.76, out: nonstop, back: 1 stop via IAD; return Jan 3, 2027: American $393.76 / United $406.26, nonstop; return Jan 4, 2027: American $381.26, out: nonstop, back: 1 stop via CLT / United $406.26, nonstop; return Jan 5, 2027: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 6–7, 2027: American $354.38 / United $365.63, nonstop; return Jan 8–9, 2027: American $354.38, nonstop / United $355.63, out: nonstop, back: 1 stop via IAD; return Jan 10, 2027: American $354.38 / United $365.63, nonstop; return Jan 11, 2027: American $344.38, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop · one-way: American $206.25, nonstop
Hotels in Chicago for these nights (Dec 28 – Jan 5, 2027 · 8 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Tue, Dec 29, 2026 · round trip · return Dec 30–31: American $393.76 / United $406.26, nonstop; return Jan 1, 2027: United $393.76, out: nonstop, back: 1 stop via IAD / American $393.76, nonstop; return Jan 2, 2027: American $393.76, nonstop / United $393.76, out: nonstop, back: 1 stop via IAD; return Jan 3, 2027: American $393.76 / United $406.26, nonstop; return Jan 4, 2027: American $381.26, out: nonstop, back: 1 stop via CLT / United $406.26, nonstop; return Jan 5, 2027: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 6–7, 2027: American $354.38 / United $365.63, nonstop; return Jan 8–9, 2027: American $354.38, nonstop / United $355.63, out: nonstop, back: 1 stop via IAD; return Jan 10, 2027: American $354.38 / United $365.63, nonstop; return Jan 11, 2027: American $344.38, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop; return Jan 12, 2027: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop · one-way: American $206.25, nonstop
Hotels in Chicago for these nights (Dec 29 – Jan 5, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Wed, Dec 30, 2026 · round trip · return Dec 31: American $393.76 / United $406.26, nonstop; return Jan 1–2, 2027: United $393.76, out: nonstop, back: 1 stop via IAD / American $393.76, nonstop; return Jan 3, 2027: American $393.76 / United $406.26, nonstop; return Jan 4, 2027: American $381.26, out: nonstop, back: 1 stop via CLT / United $406.26, nonstop; return Jan 5, 2027: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 6–7, 2027: American $354.38 / United $365.63, nonstop; return Jan 8–9, 2027: American $354.38, nonstop / United $355.63, out: nonstop, back: 1 stop via IAD; return Jan 10, 2027: American $354.38 / United $365.63, nonstop; return Jan 11, 2027: American $344.38, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop; return Jan 12, 2027: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 13, 2027: American $354.38 / United $365.63, nonstop · one-way: American $206.25, nonstop
Hotels in Chicago for these nights (Dec 30 – Jan 5, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Thu, Dec 31, 2026 · round trip · return Jan 1–2, 2027: United $393.76, out: nonstop, back: 1 stop via IAD / American $393.76, nonstop; return Jan 3, 2027: American $393.76 / United $406.26, nonstop; return Jan 4, 2027: American $381.26, out: nonstop, back: 1 stop via CLT / United $406.26, nonstop; return Jan 5, 2027: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 6–7, 2027: American $354.38 / United $365.63, nonstop; return Jan 8–9, 2027: American $354.38, nonstop / United $355.63, out: nonstop, back: 1 stop via IAD; return Jan 10, 2027: American $354.38 / United $365.63, nonstop; return Jan 11, 2027: American $344.38, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop; return Jan 12, 2027: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 13–14, 2027: American $354.38 / United $365.63, nonstop · one-way: American $206.25, nonstop
Hotels in Chicago for these nights (Dec 31 – Jan 5, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Greensboro/High Point to Chicago flights in January 2027: price by departure date

GSO → ORD · USD · 1 adult · economy · published Oct 29, 2026

Fri, Jan 1, 2027 · round trip · return Jan 2: American $393.76, nonstop / United $393.76, out: nonstop, back: 1 stop via IAD; return Jan 3: American $393.76 / United $406.26, nonstop; return Jan 4: American $381.26, out: nonstop, back: 1 stop via CLT / United $406.26, nonstop; return Jan 5: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 6–7: American $354.38 / United $365.63, nonstop; return Jan 8–9: American $354.38, nonstop / United $355.63, out: nonstop, back: 1 stop via IAD; return Jan 10: American $354.38 / United $365.63, nonstop; return Jan 11: American $344.38, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop; return Jan 12: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 13–14: American $354.38 / United $365.63, nonstop; return Jan 15: American $354.38, nonstop / United $355.63, out: nonstop, back: 1 stop via IAD · one-way: American $206.25, nonstop
Hotels in Chicago for these nights (Jan 1–5, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sat, Jan 2, 2027 · round trip · return Jan 3: American $381.26, out: 1 stop via CLT, back: nonstop / United $406.26, nonstop; return Jan 4: American $368.76, out: 1 stop via CLT, back: 1 stop via CLT / United $406.26, nonstop; return Jan 5: American $331.88, out: 1 stop via CLT, back: 1 stop via DCA / United $365.63, nonstop; return Jan 6–7: American $341.88, out: 1 stop via CLT, back: nonstop / United $365.63, nonstop; return Jan 8–9: American $341.88, out: 1 stop via CLT, back: nonstop / United $355.63, out: nonstop, back: 1 stop via IAD; return Jan 10: American $341.88, out: 1 stop via CLT, back: nonstop / United $365.63, nonstop; return Jan 11: American $331.88, out: 1 stop via CLT, back: 1 stop via CLT / United $365.63, nonstop; return Jan 12: American $331.88, out: 1 stop via CLT, back: 1 stop via DCA / United $365.63, nonstop; return Jan 13–14: American $341.88, out: 1 stop via CLT, back: nonstop / United $365.63, nonstop; return Jan 15–16: American $341.88, out: 1 stop via CLT, back: nonstop / United $355.63, out: nonstop, back: 1 stop via IAD · one-way: American $193.75, out: 1 stop via CLT
Hotels in Chicago for these nights (Jan 2–5, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sun, Jan 3, 2027 · round trip · return Jan 4: American $381.26, out: nonstop, back: 1 stop via CLT / United $406.26, nonstop; return Jan 5: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 6–7: American $354.38 / United $365.63, nonstop; return Jan 8–9: American $354.38, nonstop / United $355.63, out: nonstop, back: 1 stop via IAD; return Jan 10: American $354.38 / United $365.63, nonstop; return Jan 11: American $344.38, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop; return Jan 12: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 13–14: American $354.38 / United $365.63, nonstop; return Jan 15–16: American $354.38, nonstop / United $355.63, out: nonstop, back: 1 stop via IAD; return Jan 17: American $354.38 / United $365.63, nonstop · one-way: American $206.25, nonstop
Hotels in Chicago for these nights (Jan 3–5, 2027 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Mon, Jan 4, 2027 · round trip · return Jan 5: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 6–7: American $354.38 / United $365.63, nonstop; return Jan 8–9: American $354.38, nonstop / United $355.63, out: nonstop, back: 1 stop via IAD; return Jan 10: American $354.38 / United $365.63, nonstop; return Jan 11: American $344.38, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop; return Jan 12: American $344.38, out: nonstop, back: 1 stop via DCA / United $365.63, nonstop; return Jan 13–14: American $354.38 / United $365.63, nonstop; return Jan 15–16: American $354.38, nonstop / United $355.63, out: nonstop, back: 1 stop via IAD; return Jan 17: American $354.38 / United $365.63, nonstop; return Jan 18: American $344.38, out: nonstop, back: 1 stop via CLT / United $365.63, nonstop · one-way: American $206.25, nonstop
Hotels in Chicago for these nights (Jan 4–5, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Tue, Jan 5, 2027 · round trip · return Jan 6–7: American $315 / United $325, nonstop; return Jan 8–9: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 10: American $315 / United $325, nonstop; return Jan 11: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 12: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 13–14: American $315 / United $325, nonstop; return Jan 15: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 16: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 17: American $315 / United $325, nonstop; return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 5–11, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Wed, Jan 6, 2027 · round trip · return Jan 7: American $315 / United $325, nonstop; return Jan 8–9: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 10: American $315 / United $325, nonstop; return Jan 11: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 12: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 13–14: American $315 / United $325, nonstop; return Jan 15–16: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 17: American $315 / United $325, nonstop; return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 6–11, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Thu, Jan 7, 2027 · round trip · return Jan 8: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 9: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 10: American $315 / United $325, nonstop; return Jan 11: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 12: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 13–14: American $315 / United $325, nonstop; return Jan 15–16: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 17: American $315 / United $325, nonstop; return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 7–11, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Fri, Jan 8, 2027 · round trip · return Jan 9: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 10: American $315 / United $325, nonstop; return Jan 11: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 12: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 13–14: American $315 / United $325, nonstop; return Jan 15: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 16: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 17: American $315 / United $325, nonstop; return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $315 / United $325, nonstop; return Jan 22: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sat, Jan 9, 2027 · round trip · return Jan 10: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Jan 11: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Jan 12: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Jan 13–14: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Jan 15–16: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 17: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Jan 18: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Jan 22–23: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD · one-way: American $155, out: 1 stop via CLT
Hotels in Chicago for these nights (Jan 9–11, 2027 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sun, Jan 10, 2027 · round trip · return Jan 11: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 12: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 13–14: American $315 / United $325, nonstop; return Jan 15–16: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 17: American $315 / United $325, nonstop; return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $315 / United $325, nonstop; return Jan 22: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 23: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 24: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Mon, Jan 11, 2027 · round trip · return Jan 12: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 13–14: American $315 / United $325, nonstop; return Jan 15: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 16: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 17: American $315 / United $325, nonstop; return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $315 / United $325, nonstop; return Jan 22–23: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Tue, Jan 12, 2027 · round trip · return Jan 13–14: American $315 / United $325, nonstop; return Jan 15: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 16: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 17: American $315 / United $325, nonstop; return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $315 / United $325, nonstop; return Jan 22–23: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 12–18, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Wed, Jan 13, 2027 · round trip · return Jan 14: American $315 / United $325, nonstop; return Jan 15–16: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 17: American $315 / United $325, nonstop; return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $315 / United $325, nonstop; return Jan 22–23: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 13–18, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Thu, Jan 14, 2027 · round trip · return Jan 15–16: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 17: American $315 / United $325, nonstop; return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $315 / United $325, nonstop; return Jan 22: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 23: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 14–18, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Fri, Jan 15, 2027 · round trip · return Jan 16: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 17: American $315 / United $325, nonstop; return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $315 / United $325, nonstop; return Jan 22: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 23: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $315 / United $325, nonstop; return Jan 29: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sat, Jan 16, 2027 · round trip · return Jan 17: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Jan 18: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Jan 22–23: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 24: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Jan 25: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Jan 29–30: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD · one-way: American $155, out: 1 stop via CLT
Hotels in Chicago for these nights (Jan 16–18, 2027 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sun, Jan 17, 2027 · round trip · return Jan 18: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $315 / United $325, nonstop; return Jan 22: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 23: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $315 / United $325, nonstop; return Jan 29: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 30: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 31: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 17–18, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Mon, Jan 18, 2027 · round trip · return Jan 19: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 20–21: American $315 / United $325, nonstop; return Jan 22–23: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $315 / United $325, nonstop; return Jan 29–30: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 18–19, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Tue, Jan 19, 2027 · round trip · return Jan 20–21: American $315 / United $325, nonstop; return Jan 22: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 23: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $315 / United $325, nonstop; return Jan 29–30: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 19–25, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Wed, Jan 20, 2027 · round trip · return Jan 21: American $315 / United $325, nonstop; return Jan 22: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 23: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $315 / United $325, nonstop; return Jan 29–30: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 20–25, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Thu, Jan 21, 2027 · round trip · return Jan 22: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 23: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $315 / United $325, nonstop; return Jan 29: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 30: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 21–25, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Fri, Jan 22, 2027 · round trip · return Jan 23: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 24: American $315 / United $325, nonstop; return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $315 / United $325, nonstop; return Jan 29–30: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $315 / United $325, nonstop; return Feb 5: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sat, Jan 23, 2027 · round trip · return Jan 24: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Jan 25: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Jan 29–30: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 31: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Feb 1: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Feb 5–6: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD · one-way: American $155, out: 1 stop via CLT
Hotels in Chicago for these nights (Jan 23–25, 2027 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sun, Jan 24, 2027 · round trip · return Jan 25: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $315 / United $325, nonstop; return Jan 29–30: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $315 / United $325, nonstop; return Feb 5: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 6: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 7: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 24–25, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Mon, Jan 25, 2027 · round trip · return Jan 26: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Jan 27–28: American $315 / United $325, nonstop; return Jan 29: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 30: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $315 / United $325, nonstop; return Feb 5: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 6: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 25–26, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Tue, Jan 26, 2027 · round trip · return Jan 27–28: American $315 / United $325, nonstop; return Jan 29–30: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $315 / United $325, nonstop; return Feb 5–6: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 26 – Feb 1, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Wed, Jan 27, 2027 · round trip · return Jan 28: American $315 / United $325, nonstop; return Jan 29–30: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $315 / United $325, nonstop; return Feb 5: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 6: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 27 – Feb 1, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Thu, Jan 28, 2027 · round trip · return Jan 29: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 30: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $315 / United $325, nonstop; return Feb 5: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 6: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 28 – Feb 1, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Fri, Jan 29, 2027 · round trip · return Jan 30: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Jan 31: American $315 / United $325, nonstop; return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $315 / United $325, nonstop; return Feb 5–6: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $315 / United $325, nonstop; return Feb 12: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sat, Jan 30, 2027 · round trip · return Jan 31: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Feb 1: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Feb 5–6: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 7: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Feb 8: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Feb 12–13: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD · one-way: American $155, out: 1 stop via CLT
Hotels in Chicago for these nights (Jan 30 – Feb 1, 2027 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sun, Jan 31, 2027 · round trip · return Feb 1: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $315 / United $325, nonstop; return Feb 5–6: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $315 / United $325, nonstop; return Feb 12–13: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 14: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Jan 31 – Feb 1, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Greensboro/High Point to Chicago flights in February 2027: price by departure date

GSO → ORD · USD · 1 adult · economy · published Oct 29, 2026

Mon, Feb 1, 2027 · round trip · return Feb 2: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 3–4: American $315 / United $325, nonstop; return Feb 5–6: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $315 / United $325, nonstop; return Feb 12–13: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 14: American $315 / United $325, nonstop; return Feb 15: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Feb 1–2, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Tue, Feb 2, 2027 · round trip · return Feb 3–4: American $315 / United $325, nonstop; return Feb 5–6: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $315 / United $325, nonstop; return Feb 12–13: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 14: American $315 / United $325, nonstop; return Feb 15: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 16: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Feb 2–8, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Wed, Feb 3, 2027 · round trip · return Feb 4: American $315 / United $325, nonstop; return Feb 5: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 6: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $315 / United $325, nonstop; return Feb 12: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 13: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 14: American $315 / United $325, nonstop; return Feb 15: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 16: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 17: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Feb 3–8, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Thu, Feb 4, 2027 · round trip · return Feb 5–6: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $315 / United $325, nonstop; return Feb 12–13: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 14: American $315 / United $325, nonstop; return Feb 15: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 16: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 17–18: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Feb 4–8, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Fri, Feb 5, 2027 · round trip · return Feb 6: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 7: American $315 / United $325, nonstop; return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $315 / United $325, nonstop; return Feb 12: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 13: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 14: American $315 / United $325, nonstop; return Feb 15: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 16: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 17–18: American $315 / United $325, nonstop; return Feb 19: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD · one-way: American $165, nonstop
Hotels in Chicago for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sat, Feb 6, 2027 · round trip · return Feb 7: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Feb 8: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Feb 12–13: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 14: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Feb 15: American $295, out: 1 stop via CLT, back: 1 stop via CLT / United $325, nonstop; return Feb 16: American $295, out: 1 stop via CLT, back: 1 stop via DCA / United $325, nonstop; return Feb 17–18: American $305, out: 1 stop via CLT, back: nonstop / United $325, nonstop; return Feb 19–20: American $305, out: 1 stop via CLT, back: nonstop / United $315, out: nonstop, back: 1 stop via IAD · one-way: American $155, out: 1 stop via CLT
Hotels in Chicago for these nights (Feb 6–8, 2027 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Sun, Feb 7, 2027 · round trip · return Feb 8: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $315 / United $325, nonstop; return Feb 12–13: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 14: American $315 / United $325, nonstop; return Feb 15: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 16: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 17–18: American $315 / United $325, nonstop; return Feb 19–20: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 21: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Feb 7–8, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Mon, Feb 8, 2027 · round trip · return Feb 9: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 10–11: American $315 / United $325, nonstop; return Feb 12: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 13: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 14: American $315 / United $325, nonstop; return Feb 15: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 16: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 17–18: American $315 / United $325, nonstop; return Feb 19: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 20: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 21: American $315 / United $325, nonstop; return Feb 22: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Feb 8–9, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Tue, Feb 9, 2027 · round trip · return Feb 10–11: American $315 / United $325, nonstop; return Feb 12: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 13: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 14: American $315 / United $325, nonstop; return Feb 15: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 16: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 17–18: American $315 / United $325, nonstop; return Feb 19–20: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 21: American $315 / United $325, nonstop; return Feb 22: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 23: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Feb 9–15, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Wed, Feb 10, 2027 · round trip · return Feb 11: American $315 / United $325, nonstop; return Feb 12–13: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 14: American $315 / United $325, nonstop; return Feb 15: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 16: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 17–18: American $315 / United $325, nonstop; return Feb 19: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 20: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 21: American $315 / United $325, nonstop; return Feb 22: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 23: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 24: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Feb 10–15, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Thu, Feb 11, 2027 · round trip · return Feb 12: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 13: American $315, nonstop / United $315, out: nonstop, back: 1 stop via IAD; return Feb 14: American $315 / United $325, nonstop; return Feb 15: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 16: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 17–18: American $315 / United $325, nonstop; return Feb 19–20: United $315, out: nonstop, back: 1 stop via IAD / American $315, nonstop; return Feb 21: American $315 / United $325, nonstop; return Feb 22: American $305, out: nonstop, back: 1 stop via CLT / United $325, nonstop; return Feb 23: American $305, out: nonstop, back: 1 stop via DCA / United $325, nonstop; return Feb 24–25: American $315 / United $325, nonstop · one-way: American $165, nonstop
Hotels in Chicago for these nights (Feb 11–15, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Greensboro/High Point to Chicago nonstop flights, airlines and connections

Yes, American and United fly it nonstop. In the 4 departure dates we searched from Nov 10 to Jul 2, a nonstop from Greensboro/High Point flew on 4: Tuesdays 2 of 2 and Fridays 2 of 2. The nonstops were American (AA3390, AA3413, AA4096, AA4191, AA4205) and United (UA3626, UA4576, UA6020, UA3674, UA5934, UA4722). These are the airlines seen in the saved flights.

• American: Nonstop to Chicago
• United: Nonstop to Chicago

Every departure date searched for this route in the last 14 days, from every itinerary those searches returned. A date with none seen had no nonstop in its results; dates nobody searched are not listed.

Why book Greensboro/High Point to Chicago flights with Axel

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How we checked Greensboro/High Point to Chicago prices

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Airports covered: GSO → ORD. Each example names its actual airports.

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Planning: When to book Thanksgiving flights · Flying in December: prices, crowds and delays · How far in advance to book flights · The cheapest days of the week to fly and to book.

Trip ideas from Greensboro/High Point with Chicago (ORD)

• Best places to fly from Greensboro/High Point for Thanksgiving: fly Nov 21 – Nov 28, 2026
• Cheapest places to fly from Greensboro/High Point for 4 days: fly Dec 3 – Dec 6, 2026
• Cheapest places to fly from Greensboro/High Point in December: fly Dec 5 – Dec 12, 2026
• Best places to fly from Greensboro/High Point for Christmas: fly Dec 19 – Dec 26, 2026
• Cheapest places to fly from Greensboro/High Point for two weeks: fly Jan 9 – Jan 23, 2027
• Best places to fly from Greensboro/High Point for MLK weekend: fly Jan 15 – Jan 18, 2027
• Cheapest places to fly from Greensboro/High Point in January: fly Jan 16 – Jan 23, 2027
• Best places to fly from Greensboro/High Point for Presidents' Day weekend: fly Feb 12 – Feb 16, 2027
• Cheapest places to fly from Greensboro/High Point in February: fly Feb 13 – Feb 20, 2027
• Cheapest places to fly from Greensboro/High Point in March: fly Mar 6 – Mar 13, 2027
• Best places to fly from Greensboro/High Point for spring break: fly Mar 13 – Mar 20, 2027
• Best places to fly from Greensboro/High Point for Easter weekend: fly Mar 25 – Mar 29, 2027
• Cheapest places to fly from Greensboro/High Point in April: fly Apr 10 – Apr 17, 2027
• Cheapest places to fly from Greensboro/High Point in May: fly May 8 – May 15, 2027
• Best places to fly from Greensboro/High Point for Memorial Day weekend: fly May 28 – May 31, 2027
• Cheapest places to fly from Greensboro/High Point in June: fly Jun 12 – Jun 19, 2027
• Best places to fly from Greensboro/High Point for July 4th weekend: fly Jul 2 – Jul 5, 2027
• Fourth of July trips from Greensboro/High Point: fly Jul 2 – Jul 5, 2027
• Cheapest places to fly from Greensboro/High Point in July: fly Jul 10 – Jul 17, 2027
• Cheapest places to fly from Greensboro/High Point in August: fly Aug 7 – Aug 14, 2027
• Best places to fly from Greensboro/High Point for Labor Day weekend: fly Sep 3 – Sep 6, 2027
• Cheapest places to fly from Greensboro/High Point in September: fly Sep 11 – Sep 18, 2027
• Bachelorette and bachelor party trips from Greensboro/High Point, priced for 6
• Cheapest places to fly from Greensboro/High Point for a week
• Cheapest places to fly from Greensboro/High Point in November
• Gay & LGBTQ+ friendly cities to visit from Greensboro/High Point
• The best US cities to visit from Greensboro/High Point

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Source: https://helloaxel.com/en/flights/from-greensboro-high-point-gso-to-chicago-ord

Hotels in Chicago with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Chicago has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Chicago: the 10 best neighborhoods, ranked · Chicago hotels where a family of four can share one room

Hotel details in Chicago: AC Hotels by Marriott Chicago Downtown · Hilton Garden Inn Chicago Downtown Riverwalk · Sports Illustrated Resorts Chicago · All 200 hotels in Chicago

Near ORD: Hilton Garden Inn Hoffman Estates (Riverwoods) · Four Points by Sheraton Buffalo Grove (Buffalo Grove)

For AI assistants

• This page: Greensboro/High Point to Chicago (ORD) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
• Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.