Cheyenne to Chicago (ORD) flights from $389.50 round trip, Nov 2026–Feb 2027

Axel-exclusive from $389.50 round trip (Mon Feb 1–Tue Feb 2, 2027, United 1 stop), published Oct 29, 2026; one-way from $228 (Mon Feb 1, United 1 stop). 90 departure dates priced, one adult, economy.

Compare flight prices from Cheyenne 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 Cheyenne 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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Cheyenne to Chicago flight prices at a glance

  • One-way: from $228 (United, 1 stop) on Mon, Feb 1, 2027; one-way totals sit beside each departure in the calendar.

Cheyenne 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, 20262United, 1 stop$410Weekend of Sat, Nov 14
Sat, Nov 14, 2026Fri, Nov 20, 20266United, 1 stop$410Cheapest week in Nov 2026
Fri, Nov 20, 2026Mon, Nov 30, 202610United, 1 stop$410Thanksgiving week
Thu, Nov 26, 2026Mon, Nov 30, 20264United, 1 stop$461.25Weekend of Sat, Nov 28
Tue, Dec 1, 2026Mon, Dec 7, 20266United, 1 stop$410Cheapest week in Dec 2026
Thu, Dec 3, 2026Sun, Dec 6, 20263United, 1 stop$410Weekend of Sat, Dec 5
Sat, Dec 5, 2026Mon, Dec 7, 20262United, 1 stop$410Weekend of Sat, Dec 5
Sat, Dec 12, 2026Mon, Dec 14, 20262United, 1 stop$410Weekend of Sat, Dec 12
Fri, Dec 18, 2026Mon, Dec 28, 202610United, 1 stop$451Christmas week
Thu, Dec 24, 2026Mon, Dec 28, 20264United, 1 stop$512.50Weekend of Sat, Dec 26
Mon, Dec 28, 2026Mon, Jan 4, 20277United, 1 stop$451New Year’s week
Thu, Dec 31, 2026Mon, Jan 4, 20274United, 1 stop$451Weekend of Sat, Jan 2

Cheyenne to Chicago one-way flight prices

Cheapest one-way: $228 on Mon, Feb 1, 2027, United, 1 stop. One-way totals run $228 to $312 across 90 departure dates; each departure in the calendar below lists its one-way price beside the round trips. Published Oct 29, 2026.

Cheyenne to Chicago round trip flight prices and average fare

Published round trips start at $389.50 and run to $512.50 for the lowest fare on each of 90 departure dates; the median lowest round trip is $410, and 64 of the 90 dates have a round trip at $410 or less. One adult, economy, Axel-exclusive totals including required taxes. Published Oct 29, 2026.

Cheapest day of week and month to fly Cheyenne to Chicago

Cheapest month by published price: February 2027, where the lowest round trip per departure date has a median of $389.50; dearest: November 2026 at $461.25. Published Oct 29, 2026.

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

Cheyenne (CYS) 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.

United, out: 1 stop via DEN, back: 1 stop via DEN, from $389.50 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.

Cheyenne to Chicago flight prices by month

November 2026: Nov 14–20 from $410 · Nov 21–29 from $461.25 · Nov 30 from $410.

December 2026: Dec 1–17 from $410 · Dec 18 from $451 · Dec 19–20 from $512.50 · Dec 21–27 from $471.50 · Dec 28–31 from $451.

January 2027: Jan 1–3 from $451 · Jan 4–17 from $410 · Jan 18–31 from $399.75.

February 2027: Feb 1–11 from $389.50.

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

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

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

Sat, Nov 14, 2026 · round trip · return Nov 15–20: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 21–28: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 14–15, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Nov 15, 2026 · round trip · return Nov 16–20: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 21–29: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 15–16, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Nov 16, 2026 · round trip · return Nov 17–20: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 21–29: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Nov 17, 2026 · round trip · return Nov 18–20: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 21–29: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 1: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 17–18, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Nov 18, 2026 · round trip · return Nov 19–20: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 21–29: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 2: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 18–19, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Nov 19, 2026 · round trip · return Nov 20: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 21–29: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 3: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 19–20, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Nov 20, 2026 · round trip · return Nov 21–29: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 4: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 20–30, 2026 · 10 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Nov 21, 2026 · round trip · return Nov 22–29: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 5: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $300, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 21–30, 2026 · 9 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Nov 22, 2026 · round trip · return Nov 23–29: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 6: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $300, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 22–30, 2026 · 8 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Nov 23, 2026 · round trip · return Nov 24–29: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 7: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $300, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 23–30, 2026 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Nov 24, 2026 · round trip · return Nov 25–29: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 8: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $300, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 24–30, 2026 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Nov 25, 2026 · round trip · return Nov 26–29: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 9: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $300, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 25–30, 2026 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Nov 26, 2026 · round trip · return Nov 27–29: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 10: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $300, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 26–30, 2026 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Nov 27, 2026 · round trip · return Nov 28–29: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 11: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $300, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Nov 28, 2026 · round trip · return Nov 29: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Nov 30–Dec 12: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $300, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 28–30, 2026 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Nov 29, 2026 · round trip · return Nov 30–Dec 13: United $461.25, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $300, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 29–30, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Nov 30, 2026 · round trip · return Dec 1–14: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Nov 30 – Dec 1, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

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

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

Tue, Dec 1, 2026 · round trip · return Dec 2–15: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 1–2, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Dec 2, 2026 · round trip · return Dec 3–16: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 2–3, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Dec 3, 2026 · round trip · return Dec 4–17: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 3–4, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Dec 4, 2026 · round trip · return Dec 5–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 4–5, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Dec 5, 2026 · round trip · return Dec 6–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 5–6, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Dec 6, 2026 · round trip · return Dec 7–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–20: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 6–7, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Dec 7, 2026 · round trip · return Dec 8–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–21: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 7–8, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Dec 8, 2026 · round trip · return Dec 9–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–22: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 8–9, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Nobu Hotel Chicago, $393 total

Wed, Dec 9, 2026 · round trip · return Dec 10–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–23: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 9–10, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $83 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Nobu Hotel Chicago, $407 total

Thu, Dec 10, 2026 · round trip · return Dec 11–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–24: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 10–11, 2026 · 1 night · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $92 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $232 total

Fri, Dec 11, 2026 · round trip · return Dec 12–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–25: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 11–12, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $119 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $69 total · 5★ Sofitel Chicago Magnificent Mile, $391 total

Sat, Dec 12, 2026 · round trip · return Dec 13–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–26: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 12–13, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $113 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $69 total · 5★ Sofitel Chicago Magnificent Mile, $362 total

Sun, Dec 13, 2026 · round trip · return Dec 14–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–27: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 13–14, 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

Mon, Dec 14, 2026 · round trip · return Dec 15–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–27: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 14–15, 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, $206 total

Tue, Dec 15, 2026 · round trip · return Dec 16–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–27: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28–29: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 15–16, 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, $274 total

Wed, Dec 16, 2026 · round trip · return Dec 17–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–27: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28–30: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 16–17, 2026 · 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, $202 total

Thu, Dec 17, 2026 · round trip · return Dec 18: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 19–27: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28–31: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 17–18, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $89 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $210 total

Fri, Dec 18, 2026 · round trip · return Dec 19–27: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 1, 2027: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 18–28, 2026 · 10 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $1,032 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $404 total · 5★ Sofitel Chicago Magnificent Mile, $2,383 total

Sat, Dec 19, 2026 · round trip · return Dec 20–27: United $533, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 2, 2027: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $312, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 19–28, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $899 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $335 total · 5★ Sofitel Chicago Magnificent Mile, $2,181 total

Sun, Dec 20, 2026 · round trip · return Dec 21–27: United $533, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 3, 2027: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $312, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 20–28, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $769 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $266 total · 5★ Sofitel Chicago Magnificent Mile, $1,867 total

Mon, Dec 21, 2026 · round trip · return Dec 22–27: United $533, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 3, 2027: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4, 2027: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $312, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 21 – Jan 4, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,479 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $807 total · 5★ Sofitel Chicago Magnificent Mile, $3,522 total

Tue, Dec 22, 2026 · round trip · return Dec 23–27: United $533, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 3, 2027: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–5, 2027: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $312, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 22 – Jan 4, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,377 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $788 total · 5★ Sofitel Chicago Magnificent Mile, $3,315 total

Wed, Dec 23, 2026 · round trip · return Dec 24–27: United $533, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 3, 2027: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–6, 2027: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $312, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 23 – Jan 4, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,282 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $769 total · 5★ Sofitel Chicago Magnificent Mile, $3,109 total

Thu, Dec 24, 2026 · round trip · return Dec 25–27: United $533, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 3, 2027: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–7, 2027: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $312, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 24 – Jan 4, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,189 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $750 total · 5★ Sofitel Chicago Magnificent Mile, $2,830 total

Fri, Dec 25, 2026 · round trip · return Dec 26–27: United $533, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 3, 2027: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–8, 2027: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $312, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 25 – Jan 4, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,082 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $731 total · 5★ Sofitel Chicago Magnificent Mile, $2,565 total

Sat, Dec 26, 2026 · round trip · return Dec 27: United $533, out: 1 stop via DEN, back: 1 stop via DEN; return Dec 28, 2026–Jan 3, 2027: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–9, 2027: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $312, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 26 – Jan 4, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $991 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $621 total · 5★ Sofitel Chicago Magnificent Mile, $2,351 total

Sun, Dec 27, 2026 · round trip · return Dec 28, 2026–Jan 3, 2027: United $512.50, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–10, 2027: United $471.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $312, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 27 – Jan 4, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $900 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $579 total · 5★ Sofitel Chicago Magnificent Mile, $2,142 total

Mon, Dec 28, 2026 · round trip · return Dec 29, 2026–Jan 3, 2027: United $492, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–11, 2027: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $288, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 28 – Jan 4, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $805 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $560 total · 5★ Sofitel Chicago Magnificent Mile, $1,857 total

Tue, Dec 29, 2026 · round trip · return Dec 30, 2026–Jan 3, 2027: United $492, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–12, 2027: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $288, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 29 – Jan 4, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $703 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $538 total · 5★ Sofitel Chicago Magnificent Mile, $1,623 total

Wed, Dec 30, 2026 · round trip · return Dec 31, 2026–Jan 3, 2027: United $492, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–13, 2027: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $288, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 30 – Jan 4, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $608 total · 4★ Freehand Chicago, $487 total · 5★ Sofitel Chicago Magnificent Mile, $1,338 total

Thu, Dec 31, 2026 · round trip · return Jan 1–3, 2027: United $492, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–14, 2027: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $288, out: 1 stop via DEN
Hotels in Chicago for these nights (Dec 31 – Jan 4, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $481 total · 4★ Freehand Chicago, $404 total · 5★ Sofitel Chicago Magnificent Mile, $1,132 total

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

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

Fri, Jan 1, 2027 · round trip · return Jan 2–3: United $492, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–15: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $288, out: 1 stop via DEN
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: United $492, out: 1 stop via DEN, back: 1 stop via DEN; return Jan 4–16: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $288, out: 1 stop via DEN
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 4–17: United $451, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $288, out: 1 stop via DEN
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 5–18: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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 6–19: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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 7–20: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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 8–21: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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 9–22: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, 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, $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 10–23: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, 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, $73 total · 4★ Freehand Chicago, $80 total · 5★ Sofitel Chicago Magnificent Mile, $202 total

Sun, Jan 10, 2027 · round trip · return Jan 11–24: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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 12–25: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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 13–26: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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 14–27: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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 15–28: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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 16–29: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, 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, $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 17–30: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, 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, $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 18–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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 19–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 18 – Feb 1, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,062 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $960 total · 5★ Nobu Hotel Chicago, $5,106 total

Tue, Jan 19, 2027 · round trip · return Jan 20–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–2: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 19 – Feb 1, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $989 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $889 total · 5★ Nobu Hotel Chicago, $4,759 total

Wed, Jan 20, 2027 · round trip · return Jan 21–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–3: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 20 – Feb 1, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $905 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $818 total · 5★ Nobu Hotel Chicago, $4,395 total

Thu, Jan 21, 2027 · round trip · return Jan 22–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–4: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 21 – Feb 1, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $820 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $747 total · 5★ Nobu Hotel Chicago, $4,031 total

Fri, Jan 22, 2027 · round trip · return Jan 23–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–5: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 22 – Feb 1, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $747 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $728 total · 5★ Nobu Hotel Chicago, $3,663 total

Sat, Jan 23, 2027 · round trip · return Jan 24–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–6: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 23 – Feb 1, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $674 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $631 total · 5★ Nobu Hotel Chicago, $3,274 total

Sun, Jan 24, 2027 · round trip · return Jan 25–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–7: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 24 – Feb 1, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $601 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $534 total · 5★ Nobu Hotel Chicago, $2,903 total

Mon, Jan 25, 2027 · round trip · return Jan 26–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–8: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 25 – Feb 1, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $531 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $454 total · 5★ Nobu Hotel Chicago, $2,570 total

Tue, Jan 26, 2027 · round trip · return Jan 27–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–9: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 26 – Feb 1, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $458 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $435 total · 5★ Sofitel Chicago Magnificent Mile, $1,701 total

Wed, Jan 27, 2027 · round trip · return Jan 28–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–10: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 27 – Feb 1, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $377 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $355 total · 5★ Sofitel Chicago Magnificent Mile, $1,321 total

Thu, Jan 28, 2027 · round trip · return Jan 29–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–11: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 28 – Feb 1, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $304 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $275 total · 5★ Sofitel Chicago Magnificent Mile, $1,049 total

Fri, Jan 29, 2027 · round trip · return Jan 30–31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–12: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $204 total · 5★ Sofitel Chicago Magnificent Mile, $791 total

Sat, Jan 30, 2027 · round trip · return Jan 31: United $410, out: 1 stop via DEN, back: 1 stop via DEN; return Feb 1–13: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
Hotels in Chicago for these nights (Jan 30 – Feb 1, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $146 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $45 total · 5★ Sofitel Chicago Magnificent Mile, $524 total

Sun, Jan 31, 2027 · round trip · return Feb 1–14: United $399.75, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $240, out: 1 stop via DEN
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

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

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

Mon, Feb 1, 2027 · round trip · return Feb 2–15: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, out: 1 stop via DEN
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 3–16: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, out: 1 stop via DEN
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 4–17: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, out: 1 stop via DEN
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 5–18: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, out: 1 stop via DEN
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 6–19: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, out: 1 stop via DEN
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 7–20: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, out: 1 stop via DEN
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 8–21: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, out: 1 stop via DEN
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 9–22: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, out: 1 stop via DEN
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 10–23: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, 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★ The Chicago Hotel Collection Ambassador Gold Coast, $26 total · 5★ Sofitel Chicago Magnificent Mile, $262 total

Wed, Feb 10, 2027 · round trip · return Feb 11–24: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, out: 1 stop via DEN
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 12–25: United $389.50, out: 1 stop via DEN, back: 1 stop via DEN · one-way: United $228, out: 1 stop via DEN
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

Departure dateItineraries searchedNonstopAirlines and flights
Tue Nov 1024none seen—
Tue Dec 824none seen—
Fri Sep 324none seen—

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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Airports covered: CYS → 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.

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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: Cindy Lyn Motel · Homewood Suites by Hilton Chicago-Downtown · Sofitel Chicago Magnificent Mile · All 200 hotels in Chicago

Near ORD: Country Inn & Suites by Radisson, Hoffman Estates, IL (Hoffman Estates) · Red Lion Inn & Suites Elk Grove Village (Elk Grove Village)

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