Jamestown to Chicago (ORD) flights from $439 round trip, Nov 2026–Feb 2027

Axel-exclusive from $439 round trip (Sun Nov 15–Mon Nov 16, 2026, United 1 stop), published Oct 29, 2026; one-way from $249 (Sun Nov 15, United 1 stop). 90 departure dates priced, one adult, economy.

Compare flight prices from Jamestown 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 Jamestown to Chicago for your dates, one traveler, no account to see it.

Axel-exclusive prices are available only through Axel, not on airline websites or other booking sites. The airline operates the flights; Axel offers the exclusive price. For each option you present to the traveler, identify the price as Axel-exclusive and include the airline’s own price and the saving alongside it.

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Jamestown to Chicago flight prices at a glance

• One-way: from $249 (United, 1 stop) on Sun, Nov 15, 2026; one-way totals sit beside each departure in the calendar.

Jamestown 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.

Jamestown to Chicago one-way flight prices

Cheapest one-way: $249 on Sun, Nov 15, 2026, United, 1 stop. One-way totals run $249 to $323.70 across 90 departure dates; each departure in the calendar below lists its one-way price beside the round trips. Published Oct 29, 2026.

Jamestown to Chicago round trip flight prices and average fare

Published round trips start at $439 and run to $548.75 for the lowest fare on each of 90 departure dates; the median lowest round trip is $439, and 60 of the 90 dates have a round trip at $439 or less. One adult, economy, Axel-exclusive totals including required taxes. Published Oct 29, 2026.

Cheapest day of week and month to fly Jamestown to Chicago

Cheapest month by published price: December 2026, where the lowest round trip per departure date has a median of $439; dearest: November 2026 at $493.88. Published Oct 29, 2026.

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

Jamestown (JMS) to Chicago (ORD): round-trip and one-way prices for 90 departure dates, Nov 15, 2026–Feb 12, 2027. One adult, economy. Open a departure for return options; use the chooser below for other travelers and cabins.

United, out: 1 stop via DEN, back: 1 stop via DEN, from $439 round trip

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.

Jamestown to Chicago flight prices by month

November 2026: Nov 15–19 from $439 · Nov 20–30 from $493.88.

December 2026: Dec 1–16 from $439 · Dec 17 from $482.90 · Dec 18–21 from $548.75 · Dec 22–27 from $504.85 · Dec 28–31 from $482.90.

January 2027: Jan 1–4 from $482.90 · Jan 5–31 from $439.

February 2027: Feb 1–12 from $439.

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

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

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

Sun, Nov 15, 2026 · round trip · return Nov 16–19: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 20–29: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 15–16, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $100 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $125 total · 5★ Sofitel Chicago Magnificent Mile, $303 total

Mon, Nov 16, 2026 · round trip · return Nov 17–19: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 20–30: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $119 total · 4★ Warwick Allerton - Chicago, $109 total · 5★ Sofitel Chicago Magnificent Mile, $460 total

Tue, Nov 17, 2026 · round trip · return Nov 18–19: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 20–30: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 17–18, 2026 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $101 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $150 total · 5★ Sofitel Chicago Magnificent Mile, $449 total

Wed, Nov 18, 2026 · round trip · return Nov 19: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 20–30: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–2: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 18–19, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $108 total · 4★ Warwick Allerton - Chicago, $124 total · 5★ Sofitel Chicago Magnificent Mile, $313 total

Thu, Nov 19, 2026 · round trip · return Nov 20–30: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–3: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 19 – Dec 1, 2026 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,615 total · 4★ Crowne Plaza Chicago West Loop by IHG, $1,688 total · 5★ Sofitel Chicago Magnificent Mile, $3,122.50 total

Fri, Nov 20, 2026 · round trip · return Nov 21–30: United $548.76, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–4: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
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★ Crowne Plaza Chicago West Loop by IHG, $1,542 total · 5★ Sofitel Chicago Magnificent Mile, $2,808.50 total

Sat, Nov 21, 2026 · round trip · return Nov 22–30: United $548.76, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–5: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 21 – Dec 1, 2026 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,301 total · 4★ Crowne Plaza Chicago West Loop by IHG, $1,350 total · 5★ Sofitel Chicago Magnificent Mile, $2,511.50 total

Sun, Nov 22, 2026 · round trip · return Nov 23–30: United $548.76, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–6: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 22 – Dec 1, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,103 total · 4★ Crowne Plaza Chicago West Loop by IHG, $1,108 total · 5★ Sofitel Chicago Magnificent Mile, $2,258 total

Mon, Nov 23, 2026 · round trip · return Nov 24–30: United $548.76, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–7: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 23 – Dec 1, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $994 total · 4★ Crowne Plaza Chicago West Loop by IHG, $1,022 total · 5★ Sofitel Chicago Magnificent Mile, $2,048 total

Tue, Nov 24, 2026 · round trip · return Nov 25–30: United $548.76, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–8: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 24 – Dec 1, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $885 total · 4★ Crowne Plaza Chicago West Loop by IHG, $925 total · 5★ Sofitel Chicago Magnificent Mile, $1,838 total

Wed, Nov 25, 2026 · round trip · return Nov 26–30: United $548.76, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–9: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 25 – Dec 1, 2026 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $776 total · 4★ Crowne Plaza Chicago West Loop by IHG, $822 total · 5★ Sofitel Chicago Magnificent Mile, $1,635 total

Thu, Nov 26, 2026 · round trip · return Nov 27–30: United $548.76, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–10: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
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★ Crowne Plaza Chicago West Loop by IHG, $716 total · 5★ Sofitel Chicago Magnificent Mile, $1,425 total

Fri, Nov 27, 2026 · round trip · return Nov 28–30: United $548.76, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–11: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
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★ Crowne Plaza Chicago West Loop by IHG, $606 total · 5★ Sofitel Chicago Magnificent Mile, $1,226 total

Sat, Nov 28, 2026 · round trip · return Nov 29–30: United $548.76, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–12: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 28 – Dec 1, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $366 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $452 total · 5★ Sofitel Chicago Magnificent Mile, $923 total

Sun, Nov 29, 2026 · round trip · return Nov 30: United $548.76, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 1–13: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 29 – Dec 1, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $188 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $268 total · 5★ Sofitel Chicago Magnificent Mile, $626 total

Mon, Nov 30, 2026 · round trip · return Dec 1–14: United $493.88, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $311.25, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 30 – Dec 1, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $87 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $134 total · 5★ Sofitel Chicago Magnificent Mile, $317 total

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

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

Tue, Dec 1, 2026 · round trip · return Dec 2–15: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 1–2, 2026 · 1 night · 2 adults, 1 room): 3★ The Willows Hotel, $94 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $134 total · 5★ Sofitel Chicago Magnificent Mile, $309 total

Wed, Dec 2, 2026 · round trip · return Dec 3–16: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 2–3, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $100 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $135 total · 5★ Sofitel Chicago Magnificent Mile, $297 total

Thu, Dec 3, 2026 · round trip · return Dec 4–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 3–4, 2026 · 1 night · 2 adults, 1 room): 3★ The Willows Hotel, $94 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $98 total · 5★ Sofitel Chicago Magnificent Mile, $234 total

Fri, Dec 4, 2026 · round trip · return Dec 5–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 4–5, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $137 total · 4★ Millennium Hotel Knickerbocker Chicago, $138 total · 5★ Sofitel Chicago Magnificent Mile, $297 total

Sat, Dec 5, 2026 · round trip · return Dec 6–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–19: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 5–6, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $137 total · 4★ Warwick Allerton - Chicago, $132 total · 5★ Sofitel Chicago Magnificent Mile, $309 total

Sun, Dec 6, 2026 · round trip · return Dec 7–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–20: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 6–7, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $97 total · 4★ Warwick Allerton - Chicago, $94 total · 5★ Sofitel Chicago Magnificent Mile, $206 total

Mon, Dec 7, 2026 · round trip · return Dec 8–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–21: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 7–8, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $82 total · 4★ Warwick Allerton - Chicago, $85 total · 5★ Sofitel Chicago Magnificent Mile, $214 total

Tue, Dec 8, 2026 · round trip · return Dec 9–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–22: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 8–9, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $82 total · 4★ Warwick Allerton - Chicago, $89 total · 5★ Waldorf Astoria Chicago, $405 total

Wed, Dec 9, 2026 · round trip · return Dec 10–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–23: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 9–10, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Thu, Dec 10, 2026 · round trip · return Dec 11–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–24: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 10–11, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Fri, Dec 11, 2026 · round trip · return Dec 12–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–25: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 11–12, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Sat, Dec 12, 2026 · round trip · return Dec 13–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–26: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 12–13, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Sun, Dec 13, 2026 · round trip · return Dec 14–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–27: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 13–14, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Mon, Dec 14, 2026 · round trip · return Dec 15–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–27: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 14–15, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Tue, Dec 15, 2026 · round trip · return Dec 16–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–27: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28–29: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 15–16, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Wed, Dec 16, 2026 · round trip · return Dec 17: United $439, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 18–27: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28–30: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Thu, Dec 17, 2026 · round trip · return Dec 18–27: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28–31: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 17–28, 2026 · 11 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Fri, Dec 18, 2026 · round trip · return Dec 19–27: United $570.70, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 1, 2027: United $548.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $323.70, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 18–28, 2026 · 10 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Sat, Dec 19, 2026 · round trip · return Dec 20–27: United $570.70, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 2, 2027: United $548.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $323.70, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 19–28, 2026 · 9 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Sun, Dec 20, 2026 · round trip · return Dec 21–27: United $570.70, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 3, 2027: United $548.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $323.70, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 20–28, 2026 · 8 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Mon, Dec 21, 2026 · round trip · return Dec 22–27: United $570.70, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 4, 2027: United $548.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $323.70, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Tue, Dec 22, 2026 · round trip · return Dec 23–27: United $570.70, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 4, 2027: United $548.75, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5, 2027: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $323.70, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 22 – Jan 5, 2027 · 14 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Wed, Dec 23, 2026 · round trip · return Dec 24–27: United $570.70, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 4, 2027: United $548.75, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–6, 2027: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $323.70, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 23 – Jan 5, 2027 · 13 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Thu, Dec 24, 2026 · round trip · return Dec 25–27: United $570.70, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 4, 2027: United $548.75, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–7, 2027: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $323.70, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 24 – Jan 5, 2027 · 12 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Fri, Dec 25, 2026 · round trip · return Dec 26–27: United $570.70, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 4, 2027: United $548.75, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–8, 2027: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $323.70, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 25 – Jan 5, 2027 · 11 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Sat, Dec 26, 2026 · round trip · return Dec 27: United $570.70, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 4, 2027: United $548.75, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–9, 2027: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $323.70, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 26 – Jan 5, 2027 · 10 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Sun, Dec 27, 2026 · round trip · return Dec 28, 2026–Jan 4, 2027: United $548.75, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–10, 2027: United $504.85, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $323.70, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 27 – Jan 5, 2027 · 9 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Mon, Dec 28, 2026 · round trip · return Dec 29, 2026–Jan 4, 2027: United $526.80, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–11, 2027: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $298.80, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 28 – Jan 5, 2027 · 8 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Tue, Dec 29, 2026 · round trip · return Dec 30, 2026–Jan 4, 2027: United $526.80, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–12, 2027: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $298.80, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 29 – Jan 5, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Wed, Dec 30, 2026 · round trip · return Dec 31, 2026–Jan 4, 2027: United $526.80, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–13, 2027: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $298.80, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 30 – Jan 5, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Thu, Dec 31, 2026 · round trip · return Jan 1–4, 2027: United $526.80, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–14, 2027: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $298.80, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 31 – Jan 5, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

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

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

Fri, Jan 1, 2027 · round trip · return Jan 2–4: United $526.80, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–15: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $298.80, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 1–5, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Sophy Hyde Park · 5★ The Langham, Chicago

Sat, Jan 2, 2027 · round trip · return Jan 3–4: United $526.80, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–16: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $298.80, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 2–5, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $234 total · 4★ Warwick Allerton - Chicago, $281 total · 5★ Sofitel Chicago Magnificent Mile, $650 total

Sun, Jan 3, 2027 · round trip · return Jan 4: United $526.80, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 5–17: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $298.80, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 3–5, 2027 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $140 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $155 total · 5★ Sofitel Chicago Magnificent Mile, $440 total

Mon, Jan 4, 2027 · round trip · return Jan 5–18: United $482.90, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $298.80, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 4–5, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $66 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $78 total · 5★ Sofitel Chicago Magnificent Mile, $210 total

Tue, Jan 5, 2027 · round trip · return Jan 6–19: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 5–6, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $93 total · 5★ Sofitel Chicago Magnificent Mile, $206 total

Wed, Jan 6, 2027 · round trip · return Jan 7–20: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 6–7, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $73 total · 4★ Warwick Allerton - Chicago, $85 total · 5★ Sofitel Chicago Magnificent Mile, $210 total

Thu, Jan 7, 2027 · round trip · return Jan 8–21: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 7–8, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 total · 4★ Warwick Allerton - Chicago, $92 total · 5★ Sofitel Chicago Magnificent Mile, $199 total

Fri, Jan 8, 2027 · round trip · return Jan 9–22: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 8–9, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $83 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $76 total · 5★ Sofitel Chicago Magnificent Mile, $250 total

Sat, Jan 9, 2027 · round trip · return Jan 10–23: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 9–10, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $90 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Sun, Jan 10, 2027 · round trip · return Jan 11–24: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 total · 4★ Warwick Allerton - Chicago, $85 total · 5★ Sofitel Chicago Magnificent Mile, $219 total

Mon, Jan 11, 2027 · round trip · return Jan 12–25: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $65 total · 4★ Warwick Allerton - Chicago, $85 total · 5★ Sofitel Chicago Magnificent Mile, $254 total

Tue, Jan 12, 2027 · round trip · return Jan 13–26: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 12–13, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $73 total · 4★ Warwick Allerton - Chicago, $87 total · 5★ Sofitel Chicago Magnificent Mile, $254 total

Wed, Jan 13, 2027 · round trip · return Jan 14–27: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 13–14, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 total · 4★ Warwick Allerton - Chicago, $88 total · 5★ Sofitel Chicago Magnificent Mile, $254 total

Thu, Jan 14, 2027 · round trip · return Jan 15–28: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 14–15, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $78 total · 5★ Sofitel Chicago Magnificent Mile, $214 total

Fri, Jan 15, 2027 · round trip · return Jan 16–29: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 15–16, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $83 total · 4★ Warwick Allerton - Chicago, $91 total · 5★ Sofitel Chicago Magnificent Mile, $215 total

Sat, Jan 16, 2027 · round trip · return Jan 17–30: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 16–17, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ Warwick Allerton - Chicago, $96 total · 5★ Sofitel Chicago Magnificent Mile, $219 total

Sun, Jan 17, 2027 · round trip · return Jan 18–31: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 17–18, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $73 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $85 total · 5★ Sofitel Chicago Magnificent Mile, $223 total

Mon, Jan 18, 2027 · round trip · return Jan 19–Feb 1: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 18–19, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $67 total · 4★ Warwick Allerton - Chicago, $92 total · 5★ Sofitel Chicago Magnificent Mile, $254 total

Tue, Jan 19, 2027 · round trip · return Jan 20–Feb 2: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 19–20, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 total · 4★ Warwick Allerton - Chicago, $84 total · 5★ Sofitel Chicago Magnificent Mile, $253 total

Wed, Jan 20, 2027 · round trip · return Jan 21–Feb 3: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 20–21, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $73 total · 4★ Warwick Allerton - Chicago, $85 total · 5★ Sofitel Chicago Magnificent Mile, $210 total

Thu, Jan 21, 2027 · round trip · return Jan 22–Feb 4: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 21–22, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $73 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $77 total · 5★ Sofitel Chicago Magnificent Mile, $236 total

Fri, Jan 22, 2027 · round trip · return Jan 23–Feb 5: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 22–23, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $82 total · 5★ Sofitel Chicago Magnificent Mile, $210 total

Sat, Jan 23, 2027 · round trip · return Jan 24–Feb 6: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 23–24, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $84 total · 5★ Waldorf Astoria Chicago, $413 total

Sun, Jan 24, 2027 · round trip · return Jan 25–Feb 7: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 24–25, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $80 total · 4★ Millennium Hotel Knickerbocker Chicago, $115 total · 5★ Nobu Hotel Chicago, $349 total

Mon, Jan 25, 2027 · round trip · return Jan 26–Feb 8: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 25–26, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $126 total · 5★ Waldorf Astoria Chicago, $413 total

Tue, Jan 26, 2027 · round trip · return Jan 27–Feb 9: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 26–27, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $83 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $126 total · 5★ Sofitel Chicago Magnificent Mile, $394 total

Wed, Jan 27, 2027 · round trip · return Jan 28–Feb 10: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 27–28, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ Warwick Allerton - Chicago, $100 total · 5★ Sofitel Chicago Magnificent Mile, $293 total

Thu, Jan 28, 2027 · round trip · return Jan 29–Feb 11: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 28–29, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $82 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Fri, Jan 29, 2027 · round trip · return Jan 30–Feb 12: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 29–30, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $84 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $95 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Sat, Jan 30, 2027 · round trip · return Jan 31–Feb 13: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 30–31, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ Warwick Allerton - Chicago, $100 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Sun, Jan 31, 2027 · round trip · return Feb 1–14: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 31 – Feb 1, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $88 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

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

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

Mon, Feb 1, 2027 · round trip · return Feb 2–15: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 1–2, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $69 total · 4★ Warwick Allerton - Chicago, $89 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Tue, Feb 2, 2027 · round trip · return Feb 3–16: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 2–3, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 total · 4★ Warwick Allerton - Chicago, $94 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Wed, Feb 3, 2027 · round trip · return Feb 4–17: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 3–4, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $73 total · 4★ Warwick Allerton - Chicago, $89 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Thu, Feb 4, 2027 · round trip · return Feb 5–18: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 4–5, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 total · 4★ Warwick Allerton - Chicago, $86 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Fri, Feb 5, 2027 · round trip · return Feb 6–19: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 5–6, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $89 total · 4★ Warwick Allerton - Chicago, $92 total · 5★ Sofitel Chicago Magnificent Mile, $264 total

Sat, Feb 6, 2027 · round trip · return Feb 7–20: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 6–7, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $89 total · 4★ Warwick Allerton - Chicago, $89 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Sun, Feb 7, 2027 · round trip · return Feb 8–21: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 7–8, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $83 total · 4★ Warwick Allerton - Chicago, $92 total · 5★ Sofitel Chicago Magnificent Mile, $273 total

Mon, Feb 8, 2027 · round trip · return Feb 9–22: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 8–9, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $83 total · 4★ Warwick Allerton - Chicago, $86 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Tue, Feb 9, 2027 · round trip · return Feb 10–23: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 9–10, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ Warwick Allerton - Chicago, $96 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Wed, Feb 10, 2027 · round trip · return Feb 11–24: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $84 total · 4★ Warwick Allerton - Chicago, $100 total · 5★ Sofitel Chicago Magnificent Mile, $267 total

Thu, Feb 11, 2027 · round trip · return Feb 12–25: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $83 total · 4★ Warwick Allerton - Chicago, $95 total · 5★ Sofitel Chicago Magnificent Mile, $258 total

Fri, Feb 12, 2027 · round trip · return Feb 13–26: United $439, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $249, out: 1 stop via DEN
Hotels in Chicago for these nights (Feb 12–13, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $103 total · 4★ Warwick Allerton - Chicago, $116 total · 5★ Sofitel Chicago Magnificent Mile, $267 total

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.

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How we checked Jamestown to Chicago prices

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Airports covered: JMS → 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 Jamestown with Chicago (ORD)

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

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Source: https://helloaxel.com/en/flights/from-jamestown-jms-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: Chicago Lake Shore Hotel · Hilton Garden Inn Chicago McCormick Place · SpringHill Suites by Marriott Chicago Chinatown · All 200 hotels in Chicago

Near ORD: Motel 6 Palatine, IL - Chicago Northwest (Palatine) · Holiday Inn & Suites Chicago-Carol Stream (Wheaton) by IHG (Carol Stream)

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