$105+ Cheap flights from Colorado to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from Colorado to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Colorado to Chicago
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Cheapest flights from Colorado to ChicagoExplore the most affordable flight options available from Colorado to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from Colorado to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
This Frontier deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:55 pm -
Nonstop2h 26m
Mon 11/98:30 pm -
1 stop12h 52m
Deal found 10/23![Frontier logo]()
$190
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:50 am -
2 stops8h 00m
Tue 12/13:45 pm -
1 stop4h 40m
Deal found 10/22![Southwest logo]()
$190
This Mytrip deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:25 am -
2 stops19h 50m
Sun 12/68:53 pm -
1 stop12h 57m
Deal found 10/24![Frontier logo]()
$191
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:10 pm -
1 stop12h 36m
Sun 11/157:50 pm -
1 stop13h 32m
Deal found 10/22![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:41 am -
1 stop12h 01m
Sun 12/138:37 pm -
1 stop25h 53m
Deal found 10/22![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:26 pm -
Nonstop2h 27m
Tue 12/17:00 am -
Nonstop3h 02m
Deal found 10/24![Frontier logo]()
$193
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:00 am -
1 stop5h 35m
Thu 11/2610:30 am -
1 stop5h 00m
Deal found 10/22![Southwest logo]()
$193
This Frontier deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:55 pm -
Nonstop2h 26m
Sun 11/87:50 pm -
1 stop13h 32m
Deal found 10/24![Frontier logo]()
$194
This Frontier deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/118:40 pm -
1 stop12h 05m
Tue 12/1512:28 pm -
1 stop8h 29m
Deal found 10/23![Frontier logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:30 am -
1 stop20h 43m
Wed 11/116:30 am -
Nonstop2h 56m
Deal found 10/21![Frontier logo]()
$195
This Cheapflightsfares deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:41 am -
1 stop12h 06m
Tue 11/1012:27 pm -
1 stop10h 07m
Deal found 10/24![Frontier logo]()
$195
This Mytrip deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:41 am -
2 stops11h 32m
Tue 11/177:35 pm -
2 stops21h 18m
Deal found 10/24![Frontier logo]()
$196
Best flights from Colorado to ChicagoDiscover carefully curated flight deals from Colorado to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Colorado to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:00 am -
1 stop5h 35m
Thu 11/2610:30 am -
1 stop5h 00m
Deal found 10/22![Southwest logo]()
$193
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:30 am -
1 stop7h 25m
Thu 11/2611:18 am -
1 stop5h 09m
Deal found 10/22![Delta logo]()
$199
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:45 am -
Nonstop2h 51m
Mon 12/1412:59 pm -
1 stop4h 25m
Deal found 10/24![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:09 pm -
1 stop9h 13m
Thu 12/315:00 am -
1 stop6h 09m
Deal found 10/25![American Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:36 am -
1 stop6h 54m
Sun 11/156:23 am -
1 stop4h 35m
Deal found 10/23![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/135:25 pm -
Nonstop2h 25m
Tue 2/166:15 am -
Nonstop2h 45m
Deal found 10/21![Southwest logo]()
$208
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:08 am -
1 stop7h 31m
Sun 11/156:23 am -
1 stop4h 35m
Deal found 10/22![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/258:55 pm -
Nonstop2h 20m
Mon 11/3010:50 pm -
Nonstop2h 50m
Deal found 10/23![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:05 pm -
Nonstop2h 25m
Tue 12/88:05 am -
Nonstop2h 55m
Deal found 10/24![Southwest logo]()
$221
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/296:45 am -
1 stop4h 52m
Mon 2/112:15 pm -
1 stop4h 41m
Deal found 10/23![Delta logo]()
$238
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:40 pm -
Nonstop2h 15m
Mon 11/3010:50 pm -
Nonstop2h 50m
Deal found 10/22![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:10 am -
1 stop5h 51m
Mon 12/149:37 am -
1 stop6h 38m
Deal found 10/24![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:45 am -
1 stop5h 40m
Mon 12/148:55 pm -
Nonstop2h 45m
Deal found 10/24![Southwest logo]()
$231
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:59 am -
1 stop7h 59m
Tue 12/155:00 am -
1 stop7h 29m
Deal found 10/20![American Airlines logo]()
$358
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1712:32 pm -
Nonstop3h 09m
Thu 12/248:53 am -
Nonstop3h 58m
Deal found 10/24![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:30 am -
1 stop7h 23m
Tue 1/197:00 am -
1 stop8h 05m
Deal found 10/24![Delta logo]()
$263
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2412:32 pm -
Nonstop3h 09m
Fri 1/18:53 am -
Nonstop3h 58m
Deal found 10/20![United Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
1 stop8h 00m
Tue 11/173:52 pm -
1 stop7h 42m
Deal found 10/20![American Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/174:15 pm -
Nonstop2h 20m
Tue 11/2410:50 pm -
Nonstop2h 50m
Deal found 10/20![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/111:26 pm -
1 stop7h 09m
Wed 1/209:59 am -
1 stop7h 05m
Deal found 10/24![Delta logo]()
$263
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/25:47 am -
Nonstop2h 58m
Wed 2/37:45 pm -
Nonstop3h 14m
Deal found 10/20![United Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:43 am -
Nonstop2h 46m
Sun 12/137:00 am -
1 stop6h 37m
Deal found 10/21![United Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/146:00 am -
1 stop9h 10m
Sun 1/175:00 am -
1 stop7h 30m
Deal found 10/24![American Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/91:25 pm -
Nonstop2h 15m
Fri 2/1212:55 pm -
1 stop5h 50m
Deal found 10/23![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1912:55 am -
1 stop7h 54m
Wed 1/209:59 am -
1 stop7h 05m
Deal found 10/24![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/273:35 pm -
1 stop4h 58m
Sun 1/318:55 am -
Nonstop3h 58m
Deal found 10/22![United Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop6h 40m
Wed 11/115:00 am -
1 stop7h 28m
Deal found 10/23![American Airlines logo]()
$419
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:25 pm -
1 stop4h 15m
Tue 12/295:05 am -
1 stop5h 40m
Deal found 10/21![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:36 am -
1 stop6h 28m
Sun 11/159:30 am -
1 stop6h 44m
Deal found 10/20![Delta logo]()
$306
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1812:50 pm -
Nonstop3h 09m
Sun 3/217:15 am -
1 stop6h 33m
Deal found 10/24![United Airlines logo]()
$391
Last-minute flights from Colorado to ChicagoDiscover last-minute flight deals from Colorado to Chicago. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado to Chicago. Data last updated October 25, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:55 pm -
Nonstop2h 26m
Thu 11/126:30 am -
Nonstop2h 56m
Deal found 10/20![Frontier logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/44:17 pm -
1 stop5h 56m
Tue 11/104:36 pm -
1 stop16h 46m
Deal found 10/20![Frontier logo]()
$201
This CheapOair deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:12 pm -
1 stop21h 47m
Mon 11/97:50 pm -
1 stop13h 32m
Deal found 10/21![Frontier logo]()
$203
This Cheapflightsfares deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:41 am -
1 stop12h 06m
Tue 11/1012:27 pm -
1 stop10h 07m
Deal found 10/24![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/911:21 am -
2 stops11h 26m
Thu 11/196:42 pm -
1 stop12h 54m
Deal found 10/20![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:31 pm -
2 stops15h 54m
Mon 11/166:42 pm -
1 stop14h 40m
Deal found 10/21![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:30 am -
2 stops16h 17m
Mon 11/166:42 pm -
2 stops22h 11m
Deal found 10/21![Frontier logo]()
$203
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:36 am -
1 stop6h 28m
Wed 11/1810:34 am -
1 stop6h 28m
Deal found 10/21![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1911:20 am -
1 stop4h 35m
Thu 11/2612:45 pm -
Nonstop2h 40m
Deal found 10/20![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:00 am -
1 stop5h 35m
Thu 11/2610:30 am -
1 stop5h 00m
Deal found 10/22![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/258:55 pm -
Nonstop2h 20m
Mon 11/3010:50 pm -
Nonstop2h 50m
Deal found 10/21![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:50 am -
2 stops8h 00m
Tue 12/13:45 pm -
1 stop4h 40m
Deal found 10/22![Southwest logo]()
$190
One-way flights from Colorado to ChicagoSearch for one-way flight options from Colorado to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Colorado to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Super.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:55 pm -
Nonstop2h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$105
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/169:19 pm -
2 stops25h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$105
This Super.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:30 am -
1 stop20h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:00 am -
1 stop10h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$106
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/187:25 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$107
This Mytrip deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/109:20 pm -
2 stops20h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$108
This CheapOair deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:20 pm -
1 stop11h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$108
This Mytrip deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:10 am -
2 stops13h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/174:09 pm -
2 stops25h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:10 am -
2 stops16h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/257:39 am -
1 stop10h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$111
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:45 pm -
1 stop3h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$111
Find flight deals from Colorado to Chicago
Keep the following information in mind while searching for Colorado to Chicago flight deals. Data was last updated October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $190 (Kiwi.com) |
One-way from | $105 (Super.com) |
Popular in | July |
Cheapest in | January |
Average price | $289 |
Good round-trip deal | $343 or less |
Good one-way deal | $190 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Colorado to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 25, 2026.
Use the filters below to find and compare flights from Colorado to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Tue 12/29
6:45 pm-11:25 pm
1 stop3h 40m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Sat 11/21
5:58 pm-9:30 pm
Nonstop2h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Thu 12/31
8:57 pm-12:30 am
Nonstop2h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
Quickest round-trip
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Fri 12/11
8:40 pm-11:55 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Mon 11/16
7:05 am-10:30 am
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Thu 1/21
4:00 pm-7:25 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Wed 12/16
11:43 am-3:30 pm
Nonstop2h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Tue 12/8
1:40 pm-10:54 pm
1 stop8h 14m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$140
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Thu 11/19
1:31 pm-8:49 pm
1 stop6h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$140
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Mon 11/9
7:45 pm-5:45 am
1 stop9h 00m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$140
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Colorado to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Colorado with our price prediction graph.
DEN-ORD
DEN-MDW
COS-MDW
ASE-ORD
GJT-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Colorado to Chicago
USCO-CHI
DEN-ORD
DEN-MDW
COS-MDW
ASE-ORD
What is the cheapest month to book a flight from Colorado to Chicago?
Currently, January is the cheapest month in which you can book a flight from Colorado to Chicago (average of $243). Flying from Colorado to Chicago in July is currently the most expensive (average of $356). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CO to CHI?
Find hourly flight availability from Colorado to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 25, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 37% on flights from Colorado to Chicago by exploring options for tickets in the evening.
Weekly flight availability from Colorado to Chicago
Explore weekly flight availability from Colorado to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 25, 2026.
The most flights from USCO to CHI are scheduled on a Friday (89 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (12 on average).
How much does it cost to fly round-trip from Colorado to Chicago?
Airfare is below average for this route at the moment.
Colorado to Chicago flights typically cost between $206 and $364 in November.The cheapest round-trip price found within the last 5 days was $190 on Frontier (Nov 20-Dec 4).
How far ahead should I book a flight from Colorado to Chicago?
Booking 89 days in advance of your planned departure date is, on average, the best time to get cheap flights from Colorado to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Colorado to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Colorado to Chicago. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Colorado to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Colorado to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Colorado to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 25, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Colorado to Chicago by cabin class
Find flights from Colorado to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Colorado and Chicago flights
Browse other Colorado and Chicago flight options. Last updated on October 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Colorado to Chicago flights
Consider these flights traveling from Colorado to Chicago.
Top 5 airlines flying from Colorado to Chicago
Discover the top 5 airlines that operate flights from Colorado to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$81 | Average$208 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$281 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$170 | Average$359 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$387 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$190 | Average$503 | FlexibilityNo cancel fee | On-time69% |