Middletown to Chicago (ORD) flights from $301.63 round trip, Nov 2026–Feb 2027

Axel-exclusive from $301.63 round trip (Sat Jan 9–Sun Jan 10, 2027, American 1 stop), published Oct 29, 2026; one-way from $156.75 (Sat Jan 9, American 1 stop). 90 departure dates priced, one adult, economy.

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

Axel shows the exact bookable round-trip price from Middletown to Chicago for your dates, one traveler, no account to see it.

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Middletown to Chicago flight prices at a glance

  • One-way: from $156.75 (American, 1 stop) on Sat, Jan 9, 2027; one-way totals sit beside each departure in the calendar.
  • Cheapest day to leave: Saturday departures had the lowest published round trips (median $317.50); Friday the highest (median $325).

Middletown 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.

DepartReturnNightsAirlineAxel-exclusive totalWhy this pair
Sat, Nov 14, 2026Mon, Nov 16, 20262American, 1 stop$317.50Weekend of Sat, Nov 14
Sat, Nov 14, 2026Fri, Nov 20, 20266American, 1 stop$317.50Cheapest week in Nov 2026
Sat, Nov 21, 2026Mon, Nov 23, 20262American, 1 stop$317.50Weekend of Sat, Nov 21
Sat, Nov 21, 2026Tue, Dec 1, 202610American, 1 stop$317.50Thanksgiving week
Thu, Dec 3, 2026Sun, Dec 6, 20263American, nonstop$325Weekend of Sat, Dec 5
Sat, Dec 5, 2026Mon, Dec 7, 20262American, 1 stop$317.50Weekend of Sat, Dec 5
Sat, Dec 5, 2026Fri, Dec 11, 20266American, 1 stop$317.50Cheapest week in Dec 2026
Sat, Dec 12, 2026Mon, Dec 14, 20262American, 1 stop$317.50Weekend of Sat, Dec 12
Fri, Dec 18, 2026Mon, Dec 28, 202610American, nonstop$357.50Christmas week
Sat, Dec 19, 2026Mon, Dec 21, 20262American, 1 stop$396.88Weekend of Sat, Dec 19
Fri, Jan 1, 2027Mon, Jan 4, 20273American, nonstop$339.63Weekend of Sat, Jan 2
Sat, Jan 9, 2027Fri, Jan 15, 20276American, 1 stop$301.63Cheapest week in Jan 2027

Middletown to Chicago one-way flight prices

Cheapest one-way: $156.75 on Sat, Jan 9, 2027, American, 1 stop. One-way totals run $156.75 to $227.50 across 90 departure dates; each departure in the calendar below lists its one-way price beside the round trips. Published Oct 29, 2026.

Middletown to Chicago round trip flight prices and average fare

Published round trips start at $301.63 and run to $388.38 for the lowest fare on each of 90 departure dates; the median lowest round trip is $325, and 66 of the 90 dates have a round trip at $325 or less. One adult, economy, Axel-exclusive totals including required taxes. Published Oct 29, 2026.

Cheapest day of week and month to fly Middletown to Chicago

Cheapest month by published price: January 2027, where the lowest round trip per departure date has a median of $308.76; dearest: December 2026 at $325. Cheapest day of the week to leave: Saturday (median lowest round trip $317.50); dearest: Friday ($325). Published Oct 29, 2026.

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

Middletown (MDT) 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: nonstop, from $301.63 round trip · American, nonstop, from $308.76 round trip

Saved nonstop flight times: 2h 28m outbound; 2h 8m 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.

Middletown to Chicago flight prices by month

November 2026: Nov 14 from $317.50 · Nov 15–20 from $325 · Nov 21 from $317.50 · Nov 22–23 from $325 · Nov 24–27 from $373.75 · Nov 28 from $364 · Nov 29–30 from $373.75.

December 2026: Dec 1–4 from $325 · Dec 5 from $317.50 · Dec 6–11 from $325 · Dec 12 from $317.50 · Dec 13–17 from $325 · Dec 18 from $347.75 · Dec 19 from $379 · Dec 20 from $388.38 · Dec 21–25 from $357.51 · Dec 26 from $348.13 · Dec 27 from $357.51 · Dec 28–31 from $349.38.

January 2027: Jan 1 from $339.63 · Jan 2 from $331.08 · Jan 3 from $339.63 · Jan 4–8 from $308.76 · Jan 9 from $301.63 · Jan 10–15 from $308.76 · Jan 16 from $301.63 · Jan 17–22 from $308.76 · Jan 23 from $301.63 · Jan 24–29 from $308.76 · Jan 30 from $301.63 · Jan 31 from $308.76.

February 2027: Feb 1–5 from $308.76 · Feb 6 from $301.63 · Feb 7–11 from $308.76.

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

Middletown to Chicago flights in November 2026: price by departure date

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

Sat, Nov 14, 2026 · round trip · return Nov 15–19: American $317.50, out: 1 stop via CLT, back: nonstop / United $335, nonstop; return Nov 20: American $317.50, out: 1 stop via CLT, back: nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Nov 21–23: American $317.50, out: 1 stop via CLT, back: nonstop / United $335, nonstop; return Nov 24–26: American $366.25, out: 1 stop via CLT, back: nonstop / United $385.25, nonstop; return Nov 27: American $366.25, out: 1 stop via CLT, back: nonstop / United $375.50, out: nonstop, back: 1 stop via IAD; return Nov 28: American $366.25, out: 1 stop via CLT, back: nonstop / United $385.25, nonstop · one-way: American $165, out: 1 stop via CLT
Hotels in Chicago for these nights (Nov 14–15, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $196 total · 4★ Freehand Chicago, $86 total · 5★ Sofitel Chicago Magnificent Mile, $307 total

Sun, Nov 15, 2026 · round trip · return Nov 16–19: American $325 / United $335, nonstop; return Nov 20: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Nov 21–23: American $325 / United $335, nonstop; return Nov 24–26: American $373.75 / United $385.25, nonstop; return Nov 27: American $373.75, nonstop / United $375.50, out: nonstop, back: 1 stop via IAD; return Nov 28–29: American $373.75 / United $385.25, nonstop · one-way: American $175, 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 17–19: American $325 / United $335, nonstop; return Nov 20: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Nov 21–23: American $325 / United $335, nonstop; return Nov 24–26: American $373.75 / United $385.25, nonstop; return Nov 27: American $373.75, nonstop / United $375.50, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $373.75 / United $385.25, nonstop · one-way: American $175, 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 $325 / United $335, nonstop; return Nov 20: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Nov 21–23: American $325 / United $335, nonstop; return Nov 24–26: American $373.75 / United $385.25, nonstop; return Nov 27: American $373.75, nonstop / United $375.50, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $373.75 / United $385.25, nonstop; return Dec 1: American $325 / United $335, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Nov 17–18, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $108 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $50 total · 5★ Waldorf Astoria Chicago, $491 total

Wed, Nov 18, 2026 · round trip · return Nov 19: American $325 / United $335, nonstop; return Nov 20: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Nov 21–23: American $325 / United $335, nonstop; return Nov 24–26: American $373.75 / United $385.25, nonstop; return Nov 27: American $373.75, nonstop / United $375.50, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $373.75 / United $385.25, nonstop; return Dec 1–2: American $325 / United $335, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Nov 18–19, 2026 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $108 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $50 total · 5★ Sofitel Chicago Magnificent Mile, $307 total

Thu, Nov 19, 2026 · round trip · return Nov 20: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Nov 21–23: American $325 / United $335, nonstop; return Nov 24–26: American $373.75 / United $385.25, nonstop; return Nov 27: American $373.75, nonstop / United $375.50, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $373.75 / United $385.25, nonstop; return Dec 1–3: American $325 / United $335, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Nov 19–20, 2026 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $84 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $303 total

Fri, Nov 20, 2026 · round trip · return Nov 21–23: American $325 / United $335, nonstop; return Nov 24–26: American $373.75 / United $385.25, nonstop; return Nov 27: American $373.75, nonstop / United $375.50, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $373.75 / United $385.25, nonstop; return Dec 1–3: American $325 / United $335, nonstop; return Dec 4: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD · one-way: American $175, nonstop
Hotels in Chicago for these nights (Nov 20–21, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $178 total · 4★ Freehand Chicago, $85 total · 5★ Sofitel Chicago Magnificent Mile, $302 total

Sat, Nov 21, 2026 · round trip · return Nov 22–23: American $317.50, out: 1 stop via CLT, back: nonstop / United $335, nonstop; return Nov 24–26: American $366.25, out: 1 stop via CLT, back: nonstop / United $385.25, nonstop; return Nov 27: American $366.25, out: 1 stop via CLT, back: nonstop / United $375.50, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $366.25, out: 1 stop via CLT, back: nonstop / United $385.25, nonstop; return Dec 1–3: American $317.50, out: 1 stop via CLT, back: nonstop / United $335, nonstop; return Dec 4: American $317.50, out: 1 stop via CLT, back: nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 5: American $317.50, out: 1 stop via CLT, back: nonstop / United $335, nonstop · one-way: American $165, out: 1 stop via CLT
Hotels in Chicago for these nights (Nov 21–22, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $178 total · 4★ Freehand Chicago, $85 total · 5★ Nobu Hotel Chicago, $484 total

Sun, Nov 22, 2026 · round trip · return Nov 23: American $325 / United $335, nonstop; return Nov 24–26: American $373.75 / United $385.25, nonstop; return Nov 27: American $373.75, nonstop / United $375.50, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $373.75 / United $385.25, nonstop; return Dec 1–3: American $325 / United $335, nonstop; return Dec 4: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 5–6: American $325 / United $335, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Nov 22–23, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $90 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $206 total

Mon, Nov 23, 2026 · round trip · return Nov 24–26: American $373.75 / United $385.25, nonstop; return Nov 27: American $373.75, nonstop / United $375.50, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $373.75 / United $385.25, nonstop; return Dec 1–3: American $325 / United $335, nonstop; return Dec 4: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 5–7: American $325 / United $335, nonstop · one-way: American $175, 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 $422.50 / United $435.50, nonstop; return Nov 27: American $422.50, nonstop / United $425.75, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $422.50 / United $435.50, nonstop; return Dec 1–3: American $373.75 / United $385.25, nonstop; return Dec 4: American $373.75, nonstop / United $377.75, out: nonstop, back: 1 stop via IAD; return Dec 5–8: American $373.75 / United $385.25, nonstop · one-way: American $227.50, 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 $422.50 / United $435.50, nonstop; return Nov 27: American $422.50, nonstop / United $425.75, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $422.50 / United $435.50, nonstop; return Dec 1–3: American $373.75 / United $385.25, nonstop; return Dec 4: American $373.75, nonstop / United $377.75, out: nonstop, back: 1 stop via IAD; return Dec 5–9: American $373.75 / United $385.25, nonstop · one-way: American $227.50, 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: American $422.50, nonstop / United $425.75, out: nonstop, back: 1 stop via IAD; return Nov 28–30: American $422.50 / United $435.50, nonstop; return Dec 1–3: American $373.75 / United $385.25, nonstop; return Dec 4: American $373.75, nonstop / United $377.75, out: nonstop, back: 1 stop via IAD; return Dec 5–10: American $373.75 / United $385.25, nonstop · one-way: American $227.50, 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 28–30: American $422.50 / United $435.50, nonstop; return Dec 1–3: American $373.75 / United $385.25, nonstop; return Dec 4: American $373.75, nonstop / United $377.75, out: nonstop, back: 1 stop via IAD; return Dec 5–10: American $373.75 / United $385.25, nonstop; return Dec 11: American $373.75, nonstop / United $377.75, out: nonstop, back: 1 stop via IAD · one-way: American $227.50, 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 29–30: American $412.75, out: 1 stop via CLT, back: nonstop / United $435.50, nonstop; return Dec 1–3: American $364, out: 1 stop via CLT, back: nonstop / United $385.25, nonstop; return Dec 4: American $364, out: 1 stop via CLT, back: nonstop / United $377.75, out: nonstop, back: 1 stop via IAD; return Dec 5–10: American $364, out: 1 stop via CLT, back: nonstop / United $385.25, nonstop; return Dec 11: American $364, out: 1 stop via CLT, back: nonstop / United $377.75, out: nonstop, back: 1 stop via IAD; return Dec 12: American $364, out: 1 stop via CLT, back: nonstop / United $385.25, nonstop · one-way: American $214.50, 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 $422.50 / United $435.50, nonstop; return Dec 1–3: American $373.75 / United $385.25, nonstop; return Dec 4: American $373.75, nonstop / United $377.75, out: nonstop, back: 1 stop via IAD; return Dec 5–10: American $373.75 / United $385.25, nonstop; return Dec 11: American $373.75, nonstop / United $377.75, out: nonstop, back: 1 stop via IAD; return Dec 12–13: American $373.75 / United $385.25, nonstop · one-way: American $227.50, 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 1–3: American $373.75 / United $385.25, nonstop; return Dec 4: American $373.75, nonstop / United $377.75, out: nonstop, back: 1 stop via IAD; return Dec 5–10: American $373.75 / United $385.25, nonstop; return Dec 11: American $373.75, nonstop / United $377.75, out: nonstop, back: 1 stop via IAD; return Dec 12–14: American $373.75 / United $385.25, nonstop · one-way: American $227.50, 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

Middletown to Chicago flights in December 2026: price by departure date

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

Tue, Dec 1, 2026 · round trip · return Dec 2–3: American $325 / United $335, nonstop; return Dec 4: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 5–10: American $325 / United $335, nonstop; return Dec 11: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 12–15: American $325 / United $335, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Dec 1–2, 2026 · 1 night · 2 adults, 1 room): 3★ The Willows Hotel, $91 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $86 total · 5★ Sofitel Chicago Magnificent Mile, $303 total

Wed, Dec 2, 2026 · round trip · return Dec 3: American $325 / United $335, nonstop; return Dec 4: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 5–10: American $325 / United $335, nonstop; return Dec 11: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 12–16: American $325 / United $335, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Dec 2–3, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $94 total · 4★ Freehand Chicago, $84 total · 5★ Sofitel Chicago Magnificent Mile, $302 total

Thu, Dec 3, 2026 · round trip · return Dec 4: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 5–10: American $325 / United $335, nonstop; return Dec 11: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 12–17: American $325 / United $335, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Dec 3–4, 2026 · 1 night · 2 adults, 1 room): 3★ The Willows Hotel, $91 total · 4★ Freehand Chicago, $76 total · 5★ Sofitel Chicago Magnificent Mile, $238 total

Fri, Dec 4, 2026 · round trip · return Dec 5–10: American $325 / United $335, nonstop; return Dec 11: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 12–17: American $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD · one-way: American $175, nonstop
Hotels in Chicago for these nights (Dec 4–5, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $116 total · 4★ Freehand Chicago, $86 total · 5★ Sofitel Chicago Magnificent Mile, $302 total

Sat, Dec 5, 2026 · round trip · return Dec 6–10: American $317.50, out: 1 stop via CLT, back: nonstop / United $335, nonstop; return Dec 11: American $317.50, out: 1 stop via CLT, back: nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 12–17: American $317.50, out: 1 stop via CLT, back: nonstop / United $335, nonstop; return Dec 18: American $317.50, out: 1 stop via CLT, back: nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19: American $358.13, out: 1 stop via CLT, back: nonstop / United $376.88, nonstop · one-way: American $165, out: 1 stop via CLT
Hotels in Chicago for these nights (Dec 5–6, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $116 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $65 total · 5★ Sofitel Chicago Magnificent Mile, $308 total

Sun, Dec 6, 2026 · round trip · return Dec 7–10: American $325 / United $335, nonstop; return Dec 11: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 12–17: American $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–20: American $365.63 / United $376.88, nonstop · one-way: American $175, 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 8–10: American $325 / United $335, nonstop; return Dec 11: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 12–17: American $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–21: American $365.63 / United $376.88, nonstop · one-way: American $175, 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 $325 / United $335, nonstop; return Dec 11: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 12–17: American $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–22: American $365.63 / United $376.88, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Dec 8–9, 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 9, 2026 · round trip · return Dec 10: American $325 / United $335, nonstop; return Dec 11: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 12–17: American $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–23: American $365.63 / United $376.88, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Dec 9–10, 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 10, 2026 · round trip · return Dec 11: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 12–17: American $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–24: American $365.63 / United $376.88, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Dec 10–11, 2026 · 1 night · 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 12–17: American $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–24: American $365.63 / United $376.88, nonstop; return Dec 25: American $365.63, nonstop / United $367.50, out: nonstop, back: 1 stop via IAD · one-way: American $175, nonstop
Hotels in Chicago for these nights (Dec 11–12, 2026 · 1 night · 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 13–17: American $317.50, out: 1 stop via CLT, back: nonstop / United $335, nonstop; return Dec 18: American $317.50, out: 1 stop via CLT, back: nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–24: American $358.13, out: 1 stop via CLT, back: nonstop / United $376.88, nonstop; return Dec 25: American $358.13, out: 1 stop via CLT, back: nonstop / United $367.50, out: nonstop, back: 1 stop via IAD; return Dec 26: American $358.13, out: 1 stop via CLT, back: nonstop / United $376.88, nonstop · one-way: American $165, out: 1 stop via CLT
Hotels in Chicago for these nights (Dec 12–13, 2026 · 1 night · 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 14–17: American $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–24: American $365.63 / United $376.88, nonstop; return Dec 25: American $365.63, nonstop / United $367.50, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $365.63 / United $376.88, nonstop · one-way: American $175, 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 15–17: American $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–24: American $365.63 / United $376.88, nonstop; return Dec 25: American $365.63, nonstop / United $367.50, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $365.63 / United $376.88, nonstop; return Dec 28: American $357.50 / United $368.50, nonstop · one-way: American $175, 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 $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–24: American $365.63 / United $376.88, nonstop; return Dec 25: American $365.63, nonstop / United $367.50, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $365.63 / United $376.88, nonstop; return Dec 28–29: American $357.50 / United $368.50, nonstop · one-way: American $175, 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 $325 / United $335, nonstop; return Dec 18: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–24: American $365.63 / United $376.88, nonstop; return Dec 25: American $365.63, nonstop / United $367.50, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $365.63 / United $376.88, nonstop; return Dec 28–30: American $357.50 / United $368.50, nonstop · one-way: American $175, 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: American $325, nonstop / United $327.50, out: nonstop, back: 1 stop via IAD; return Dec 19–24: American $365.63 / United $376.88, nonstop; return Dec 25: American $365.63, nonstop / United $367.50, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $365.63 / United $376.88, nonstop; return Dec 28–31: American $357.50 / United $368.50, nonstop · one-way: American $175, nonstop
Hotels in Chicago for these nights (Dec 17–18, 2026 · 1 night · 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 19–24: American $365.63 / United $376.88, nonstop; return Dec 25: American $365.63, nonstop / United $367.50, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $365.63 / United $376.88, nonstop; return Dec 28–31: American $357.50 / United $368.50, nonstop; return Jan 1, 2027: American $347.75, nonstop / United $349.90, out: nonstop, back: 1 stop via IAD · one-way: American $175, nonstop
Hotels in Chicago for these nights (Dec 18 – Jan 1, 2027 · 14 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 20–24: American $396.88, out: 1 stop via CLT, back: nonstop / United $418.76, nonstop; return Dec 25: American $396.88, out: 1 stop via CLT, back: nonstop / United $409.38, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $396.88, out: 1 stop via CLT, back: nonstop / United $418.76, nonstop; return Dec 28–31: American $388.75, out: 1 stop via CLT, back: nonstop / United $410.38, nonstop; return Jan 1, 2027: American $379, out: 1 stop via CLT, back: nonstop / United $391.78, out: nonstop, back: 1 stop via IAD; return Jan 2, 2027: American $379, out: 1 stop via CLT, back: nonstop / United $400.33, nonstop · one-way: American $206.25, out: 1 stop via CLT
Hotels in Chicago for these nights (Dec 19 – Jan 1, 2027 · 13 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 21–24: American $406.26 / United $418.76, nonstop; return Dec 25: American $406.26, nonstop / United $409.38, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $406.26 / United $418.76, nonstop; return Dec 28–31: American $398.13 / United $410.38, nonstop; return Jan 1, 2027: American $388.38, nonstop / United $391.78, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $388.38 / United $400.33, nonstop · one-way: American $218.75, nonstop
Hotels in Chicago for these nights (Dec 20 – Jan 1, 2027 · 12 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 22–24: American $406.26 / United $418.76, nonstop; return Dec 25: American $406.26, nonstop / United $409.38, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $406.26 / United $418.76, nonstop; return Dec 28–31: American $398.13 / United $410.38, nonstop; return Jan 1, 2027: American $388.38, nonstop / United $391.78, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $388.38 / United $400.33, nonstop; return Jan 4, 2027: American $357.51 / United $368.51, nonstop · one-way: American $218.75, nonstop
Hotels in Chicago for these nights (Dec 21 – Jan 4, 2027 · 14 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 $406.26 / United $418.76, nonstop; return Dec 25: American $406.26, nonstop / United $409.38, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $406.26 / United $418.76, nonstop; return Dec 28–31: American $398.13 / United $410.38, nonstop; return Jan 1, 2027: American $388.38, nonstop / United $391.78, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $388.38 / United $400.33, nonstop; return Jan 4–5, 2027: American $357.51 / United $368.51, nonstop · one-way: American $218.75, nonstop
Hotels in Chicago for these nights (Dec 22 – Jan 4, 2027 · 13 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 $406.26 / United $418.76, nonstop; return Dec 25: American $406.26, nonstop / United $409.38, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $406.26 / United $418.76, nonstop; return Dec 28–31: American $398.13 / United $410.38, nonstop; return Jan 1, 2027: American $388.38, nonstop / United $391.78, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $388.38 / United $400.33, nonstop; return Jan 4–6, 2027: American $357.51 / United $368.51, nonstop · one-way: American $218.75, nonstop
Hotels in Chicago for these nights (Dec 23 – Jan 4, 2027 · 12 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: American $406.26, nonstop / United $409.38, out: nonstop, back: 1 stop via IAD; return Dec 26–27: American $406.26 / United $418.76, nonstop; return Dec 28–31: American $398.13 / United $410.38, nonstop; return Jan 1, 2027: American $388.38, nonstop / United $391.78, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $388.38 / United $400.33, nonstop; return Jan 4–7, 2027: American $357.51 / United $368.51, nonstop · one-way: American $218.75, nonstop
Hotels in Chicago for these nights (Dec 24 – Jan 4, 2027 · 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 25, 2026 · round trip · return Dec 26–27: American $406.26 / United $418.76, nonstop; return Dec 28–31: American $398.13 / United $410.38, nonstop; return Jan 1, 2027: American $388.38, nonstop / United $391.78, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $388.38 / United $400.33, nonstop; return Jan 4–7, 2027: American $357.51 / United $368.51, nonstop; return Jan 8, 2027: American $357.51, nonstop / United $361.38, out: nonstop, back: 1 stop via IAD · one-way: American $218.75, nonstop
Hotels in Chicago for these nights (Dec 25 – Jan 4, 2027 · 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 26, 2026 · round trip · return Dec 27: American $396.88, out: 1 stop via CLT, back: nonstop / United $418.76, nonstop; return Dec 28–31: American $388.75, out: 1 stop via CLT, back: nonstop / United $410.38, nonstop; return Jan 1, 2027: American $379, out: 1 stop via CLT, back: nonstop / United $391.78, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $379, out: 1 stop via CLT, back: nonstop / United $400.33, nonstop; return Jan 4–7, 2027: American $348.13, out: 1 stop via CLT, back: nonstop / United $368.51, nonstop; return Jan 8, 2027: American $348.13, out: 1 stop via CLT, back: nonstop / United $361.38, out: nonstop, back: 1 stop via IAD; return Jan 9, 2027: American $348.13, out: 1 stop via CLT, back: nonstop / United $368.51, nonstop · one-way: American $206.25, out: 1 stop via CLT
Hotels in Chicago for these nights (Dec 26 – Jan 4, 2027 · 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 27, 2026 · round trip · return Dec 28–31: American $398.13 / United $410.38, nonstop; return Jan 1, 2027: American $388.38, nonstop / United $391.78, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $388.38 / United $400.33, nonstop; return Jan 4–7, 2027: American $357.51 / United $368.51, nonstop; return Jan 8, 2027: American $357.51, nonstop / United $361.38, out: nonstop, back: 1 stop via IAD; return Jan 9–10, 2027: American $357.51 / United $368.51, nonstop · one-way: American $218.75, nonstop
Hotels in Chicago for these nights (Dec 27 – Jan 4, 2027 · 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 28, 2026 · round trip · return Dec 29–31: American $390 / United $402, nonstop; return Jan 1, 2027: American $380.25, nonstop / United $383.40, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $380.25 / United $391.95, nonstop; return Jan 4–7, 2027: American $349.38 / United $360.13, nonstop; return Jan 8, 2027: American $349.38, nonstop / United $353, out: nonstop, back: 1 stop via IAD; return Jan 9–11, 2027: American $349.38 / United $360.13, nonstop · one-way: American $210, nonstop
Hotels in Chicago for these nights (Dec 28 – Jan 4, 2027 · 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 29, 2026 · round trip · return Dec 30–31: American $390 / United $402, nonstop; return Jan 1, 2027: American $380.25, nonstop / United $383.40, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $380.25 / United $391.95, nonstop; return Jan 4–7, 2027: American $349.38 / United $360.13, nonstop; return Jan 8, 2027: American $349.38, nonstop / United $353, out: nonstop, back: 1 stop via IAD; return Jan 9–12, 2027: American $349.38 / United $360.13, nonstop · one-way: American $210, nonstop
Hotels in Chicago for these nights (Dec 29 – Jan 4, 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, Dec 30, 2026 · round trip · return Dec 31: American $390 / United $402, nonstop; return Jan 1, 2027: American $380.25, nonstop / United $383.40, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $380.25 / United $391.95, nonstop; return Jan 4–7, 2027: American $349.38 / United $360.13, nonstop; return Jan 8, 2027: American $349.38, nonstop / United $353, out: nonstop, back: 1 stop via IAD; return Jan 9–13, 2027: American $349.38 / United $360.13, nonstop · one-way: American $210, nonstop
Hotels in Chicago for these nights (Dec 30 – Jan 4, 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, Dec 31, 2026 · round trip · return Jan 1, 2027: American $380.25, nonstop / United $383.40, out: nonstop, back: 1 stop via IAD; return Jan 2–3, 2027: American $380.25 / United $391.95, nonstop; return Jan 4–7, 2027: American $349.38 / United $360.13, nonstop; return Jan 8, 2027: American $349.38, nonstop / United $353, out: nonstop, back: 1 stop via IAD; return Jan 9–14, 2027: American $349.38 / United $360.13, nonstop · one-way: American $210, nonstop
Hotels in Chicago for these nights (Dec 31 – Jan 4, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago

Middletown to Chicago flights in January 2027: price by departure date

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

Fri, Jan 1, 2027 · round trip · return Jan 2–3: American $370.50 / United $381.90, nonstop; return Jan 4–7: American $339.63 / United $350.08, nonstop; return Jan 8: American $339.63, nonstop / United $342.95, out: nonstop, back: 1 stop via IAD; return Jan 9–14: American $339.63 / United $350.08, nonstop; return Jan 15: American $339.63, nonstop / United $342.95, out: nonstop, back: 1 stop via IAD · one-way: American $199.50, nonstop
Hotels in Chicago for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $128 total · 5★ Sofitel Chicago Magnificent Mile, $671 total

Sat, Jan 2, 2027 · round trip · return Jan 3: American $361.95, out: 1 stop via CLT, back: nonstop / United $381.90, nonstop; return Jan 4–7: American $331.08, out: 1 stop via CLT, back: nonstop / United $350.08, nonstop; return Jan 8: American $331.08, out: 1 stop via CLT, back: nonstop / United $342.95, out: nonstop, back: 1 stop via IAD; return Jan 9–14: American $331.08, out: 1 stop via CLT, back: nonstop / United $350.08, nonstop; return Jan 15: American $331.08, out: 1 stop via CLT, back: nonstop / United $342.95, out: nonstop, back: 1 stop via IAD; return Jan 16: American $331.08, out: 1 stop via CLT, back: nonstop / United $350.08, nonstop · one-way: American $188.10, out: 1 stop via CLT
Hotels in Chicago for these nights (Jan 2–4, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $158 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $109 total · 5★ Sofitel Chicago Magnificent Mile, $465 total

Sun, Jan 3, 2027 · round trip · return Jan 4–7: American $339.63 / United $350.08, nonstop; return Jan 8: American $339.63, nonstop / United $342.95, out: nonstop, back: 1 stop via IAD; return Jan 9–14: American $339.63 / United $350.08, nonstop; return Jan 15: American $339.63, nonstop / United $342.95, out: nonstop, back: 1 stop via IAD; return Jan 16–17: American $339.63 / United $350.08, nonstop · one-way: American $199.50, nonstop
Hotels in Chicago for these nights (Jan 3–4, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Mon, Jan 4, 2027 · round trip · return Jan 5–7: American $308.76 / United $318.26, nonstop; return Jan 8: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 9–14: American $308.76 / United $318.26, nonstop; return Jan 15: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–18: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 4–5, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $207 total

Tue, Jan 5, 2027 · round trip · return Jan 6–7: American $308.76 / United $318.26, nonstop; return Jan 8: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 9–14: American $308.76 / United $318.26, nonstop; return Jan 15: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–19: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 5–6, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $199 total

Wed, Jan 6, 2027 · round trip · return Jan 7: American $308.76 / United $318.26, nonstop; return Jan 8: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 9–14: American $308.76 / United $318.26, nonstop; return Jan 15: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–20: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 6–7, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $80 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $227 total

Thu, Jan 7, 2027 · round trip · return Jan 8: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 9–14: American $308.76 / United $318.26, nonstop; return Jan 15: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–21: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 7–8, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $264 total

Fri, Jan 8, 2027 · round trip · return Jan 9–14: American $308.76 / United $318.26, nonstop; return Jan 15: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 8–9, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $85 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Sat, Jan 9, 2027 · round trip · return Jan 10–14: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop; return Jan 15: American $301.63, out: 1 stop via CLT, back: nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–21: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop; return Jan 22: American $301.63, out: 1 stop via CLT, back: nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop · one-way: American $156.75, out: 1 stop via CLT
Hotels in Chicago for these nights (Jan 9–10, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ Freehand Chicago, $80 total · 5★ Sofitel Chicago Magnificent Mile, $202 total

Sun, Jan 10, 2027 · round trip · return Jan 11–14: American $308.76 / United $318.26, nonstop; return Jan 15: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–24: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ Freehand Chicago, $70 total · 5★ Sofitel Chicago Magnificent Mile, $219 total

Mon, Jan 11, 2027 · round trip · return Jan 12–14: American $308.76 / United $318.26, nonstop; return Jan 15: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–25: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $54 total · 5★ Sofitel Chicago Magnificent Mile, $206 total

Tue, Jan 12, 2027 · round trip · return Jan 13–14: American $308.76 / United $318.26, nonstop; return Jan 15: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–26: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 12–13, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $210 total

Wed, Jan 13, 2027 · round trip · return Jan 14: American $308.76 / United $318.26, nonstop; return Jan 15: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–27: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 13–14, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $199 total

Thu, Jan 14, 2027 · round trip · return Jan 15: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 16–21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–28: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 14–15, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $210 total

Fri, Jan 15, 2027 · round trip · return Jan 16–21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 15–16, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $70 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Sat, Jan 16, 2027 · round trip · return Jan 17–21: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop; return Jan 22: American $301.63, out: 1 stop via CLT, back: nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–28: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop; return Jan 29: American $301.63, out: 1 stop via CLT, back: nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop · one-way: American $156.75, out: 1 stop via CLT
Hotels in Chicago for these nights (Jan 16–17, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Sun, Jan 17, 2027 · round trip · return Jan 18–21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–31: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 17–18, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $80 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $206 total

Mon, Jan 18, 2027 · round trip · return Jan 19–21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 1: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 18–19, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $227 total

Tue, Jan 19, 2027 · round trip · return Jan 20–21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 2: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 19–20, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $80 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $206 total

Wed, Jan 20, 2027 · round trip · return Jan 21: American $308.76 / United $318.26, nonstop; return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 3: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 20–21, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Thu, Jan 21, 2027 · round trip · return Jan 22: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 23–28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 4: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 21–22, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $209 total

Fri, Jan 22, 2027 · round trip · return Jan 23–28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 22–23, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ Freehand Chicago, $80 total · 5★ Sofitel Chicago Magnificent Mile, $249 total

Sat, Jan 23, 2027 · round trip · return Jan 24–28: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop; return Jan 29: American $301.63, out: 1 stop via CLT, back: nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 4: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop; return Feb 5: American $301.63, out: 1 stop via CLT, back: nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop · one-way: American $156.75, out: 1 stop via CLT
Hotels in Chicago for these nights (Jan 23–24, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ Freehand Chicago, $78 total · 5★ Nobu Hotel Chicago, $371 total

Sun, Jan 24, 2027 · round trip · return Jan 25–28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–7: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 24–25, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $70 total · 4★ Freehand Chicago, $72 total · 5★ Nobu Hotel Chicago, $333 total

Mon, Jan 25, 2027 · round trip · return Jan 26–28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–8: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 25–26, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Nobu Hotel Chicago, $395 total

Tue, Jan 26, 2027 · round trip · return Jan 27–28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–9: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 26–27, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $81 total · 4★ Freehand Chicago, $72 total · 5★ Sofitel Chicago Magnificent Mile, $380 total

Wed, Jan 27, 2027 · round trip · return Jan 28: American $308.76 / United $318.26, nonstop; return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–10: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 27–28, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ Freehand Chicago, $72 total · 5★ Sofitel Chicago Magnificent Mile, $272 total

Thu, Jan 28, 2027 · round trip · return Jan 29: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Jan 30–Feb 4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–11: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 28–29, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Fri, Jan 29, 2027 · round trip · return Jan 30–Feb 4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 29–30, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $85 total · 4★ Freehand Chicago, $78 total · 5★ Sofitel Chicago Magnificent Mile, $267 total

Sat, Jan 30, 2027 · round trip · return Jan 31–Feb 4: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop; return Feb 5: American $301.63, out: 1 stop via CLT, back: nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–11: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop; return Feb 12: American $301.63, out: 1 stop via CLT, back: nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop · one-way: American $156.75, out: 1 stop via CLT
Hotels in Chicago for these nights (Jan 30–31, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Sun, Jan 31, 2027 · round trip · return Feb 1–4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–14: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Jan 31 – Feb 1, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Middletown to Chicago flights in February 2027: price by departure date

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

Mon, Feb 1, 2027 · round trip · return Feb 2–4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–15: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Feb 1–2, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $80 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Tue, Feb 2, 2027 · round trip · return Feb 3–4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–16: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Feb 2–3, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $267 total

Wed, Feb 3, 2027 · round trip · return Feb 4: American $308.76 / United $318.26, nonstop; return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–17: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Feb 3–4, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $80 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Thu, Feb 4, 2027 · round trip · return Feb 5: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 6–11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–18: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Feb 4–5, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Fri, Feb 5, 2027 · round trip · return Feb 6–11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–18: American $308.76 / United $318.26, nonstop; return Feb 19: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Feb 5–6, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $103 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $43 total · 5★ Sofitel Chicago Magnificent Mile, $274 total

Sat, Feb 6, 2027 · round trip · return Feb 7–11: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop; return Feb 12: American $301.63, out: 1 stop via CLT, back: nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–18: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop; return Feb 19: American $301.63, out: 1 stop via CLT, back: nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 20: American $301.63, out: 1 stop via CLT, back: nonstop / United $318.26, nonstop · one-way: American $156.75, out: 1 stop via CLT
Hotels in Chicago for these nights (Feb 6–7, 2027 · 1 night · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $101 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $43 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Sun, Feb 7, 2027 · round trip · return Feb 8–11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–18: American $308.76 / United $318.26, nonstop; return Feb 19: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 20–21: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Feb 7–8, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $80 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Mon, Feb 8, 2027 · round trip · return Feb 9–11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–18: American $308.76 / United $318.26, nonstop; return Feb 19: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 20–22: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Feb 8–9, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $80 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Tue, Feb 9, 2027 · round trip · return Feb 10–11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–18: American $308.76 / United $318.26, nonstop; return Feb 19: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 20–23: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Feb 9–10, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Wed, Feb 10, 2027 · round trip · return Feb 11: American $308.76 / United $318.26, nonstop; return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–18: American $308.76 / United $318.26, nonstop; return Feb 19: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 20–24: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Feb 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $79 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Thu, Feb 11, 2027 · round trip · return Feb 12: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 13–18: American $308.76 / United $318.26, nonstop; return Feb 19: American $308.76, nonstop / United $311.13, out: nonstop, back: 1 stop via IAD; return Feb 20–25: American $308.76 / United $318.26, nonstop · one-way: American $166.25, nonstop
Hotels in Chicago for these nights (Feb 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $85 total · 4★ Freehand Chicago, $71 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

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Hotels in Chicago with Axel

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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: Fairmont Chicago at Millennium Park · Hyatt Centric The Loop Chicago · Viceroy Chicago · All 200 hotels in Chicago

Near ORD: SpringHill Suites Chicago O'Hare (Rosemont, Illinois) · Quality Inn Schaumburg - Chicago near the Mall (Schaumburg)

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