$87+ Cheap flights from Colorado to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Jun 19 — Jun 261
Round-trip
1 adult, Economy
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Find cheap flights from Colorado to Chicago with Cheapflights
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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 May 20, 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 May 20, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/17. 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.
Sat 6/275:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 7/119:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 5/17![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Sat 11/76:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Mon 11/910:40 pm
ORD
- DEN
Nonstop2h 49m
Frontier
Deal found 5/18![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 5/17. 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 7/36:30 am
DEN
- ORD
1 stop12h 20m
Frontier
Fri 7/109:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 5/17![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/157:26 pm
DEN
- ORD
1 stop8h 41m
Frontier
Fri 6/199:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/18![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Fri 6/129:58 am
DEN
- ORD
1 stop8h 52m
Frontier
Sat 6/209:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/18![Frontier logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 5/17. 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.
Sat 6/2711:46 pm
DEN
- ORD
1 stop7h 17m
Frontier
Thu 7/29:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/17![Frontier logo]()
$186
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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 6/165:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Tue 6/239:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/19![Frontier logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 5/18. 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 6/306:30 am
DEN
- ORD
1 stop12h 20m
Frontier
Tue 7/75:46 pm
ORD
- DEN
1 stop15h 28m
Frontier
Deal found 5/18![Frontier logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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.
Sat 6/135:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 6/174:59 pm
ORD
- DEN
1 stop16h 21m
Frontier
Deal found 5/19![Frontier logo]()
$189
This Frontier deal was found by Cheapflights users on 5/18. 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.
Tue 8/411:46 pm
DEN
- ORD
1 stop7h 07m
Frontier
Tue 8/117:15 am
ORD
- DEN
1 stop11h 45m
Frontier
Deal found 5/18![Frontier logo]()
$190
This Priceline deal was found by Cheapflights users on 5/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3011:46 pm
DEN
- MDW
1 stop10h 23m
Frontier
Tue 7/712:11 pm
MDW
- DEN
1 stop10h 54m
Frontier
Deal found 5/18![Frontier logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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 6/99:06 pm
DEN
- ORD
1 stop26h 42m
Frontier
Fri 6/129:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/19![Frontier logo]()
$191
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 May 20, 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 May 20, 2026.
This Southwest deal was found by Cheapflights users on 5/17. 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 7/87:00 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 7/149:05 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 5/17![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 5/16. 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 8/59:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Sat 8/86:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Deal found 5/16![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 5/19. 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.
Wed 8/512:59 am
DEN
- ORD
1 stop5h 57m
Delta
Tue 8/116:25 am
ORD
- DEN
1 stop6h 41m
Delta
Deal found 5/19![Delta logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 7/159:15 am
DEN
- RFD
1 stop9h 44m
Multiple Airlines
Sun 7/199:19 am
RFD
- DEN
1 stop5h 56m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$326
This KAYAK deal was found by Cheapflights users on 5/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:22 am
DEN
- ORD
Nonstop2h 38m
American Airlines
Thu 6/410:30 pm
ORD
- DEN
Nonstop2h 47m
American Airlines
Deal found 5/15![American Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 5/16. 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 8/51:55 pm
DEN
- MDW
1 stop4h 30m
Southwest
Mon 8/108:45 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 5/16![Southwest logo]()
$233
This United Airlines deal was found by Cheapflights users on 5/16. 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 7/147:10 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Sat 7/187:05 am
ORD
- DEN
Nonstop2h 50m
United Airlines
Deal found 5/16![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 5/17. 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 10/55:55 am
DEN
- MDW
Nonstop2h 20m
Southwest
Thu 10/86:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 5/17![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 5/17. 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.
Wed 7/86:05 am
DEN
- MDW
1 stop5h 33m
Delta
Sun 7/129:49 am
MDW
- DEN
1 stop6h 41m
Delta
Deal found 5/17![Delta logo]()
$261
This United Airlines deal was found by Cheapflights users on 5/15. 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 6/249:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Mon 6/295:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Deal found 5/15![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 5/16. 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 8/57:25 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Sat 8/81:45 pm
MDW
- DEN
1 stop5h 55m
Southwest
Deal found 5/16![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 5/18. 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 7/1712:59 am
DEN
- MDW
1 stop7h 09m
Delta
Tue 7/217:06 pm
MDW
- DEN
1 stop5h 21m
Delta
Deal found 5/18![Delta logo]()
$261
This United Airlines deal was found by Cheapflights users on 5/15. 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 7/34:29 pm
DEN
- ORD
Nonstop2h 45m
United Airlines
Sun 7/55:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Deal found 5/15![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 5/15. 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 10/85:55 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 10/125:00 am
MDW
- DEN
1 stop4h 55m
Southwest
Deal found 5/15![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 5/19. 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 8/610:26 am
DEN
- ORD
1 stop7h 02m
Delta
Fri 8/145:57 pm
ORD
- DEN
1 stop6h 37m
Delta
Deal found 5/19![Delta logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 5/19. 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.
Thu 10/1512:45 pm
GJT
- ORD
1 stop15h 57m
Multiple Airlines
Mon 10/192:46 pm
ORD
- GJT
2 stops22h 14m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 5/19. 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 6/256:00 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Mon 6/296:00 am
ORD
- DEN
Nonstop2h 42m
United Airlines
Deal found 5/19![United Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 5/19. 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 8/66:05 am
DEN
- MDW
1 stop5h 34m
Delta
Sun 8/99:24 am
MDW
- DEN
1 stop5h 21m
Delta
Deal found 5/19![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 5/19. 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 7/2210:15 am
DEN
- MDW
1 stop5h 35m
Southwest
Mon 7/275:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 5/19![Southwest logo]()
$251
This American Airlines deal was found by Cheapflights users on 5/16. 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 7/32:21 pm
MTJ
- ORD
1 stop6h 01m
American Airlines
Tue 7/710:30 pm
ORD
- MTJ
2 stops12h 15m
American Airlines
Deal found 5/16![American Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 7/209:15 am
DEN
- RFD
1 stop10h 08m
Multiple Airlines
Thu 7/239:19 am
RFD
- DEN
1 stop5h 56m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 5/19. 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 7/410:05 am
DEN
- MDW
1 stop3h 45m
Southwest
Wed 7/84:30 pm
MDW
- DEN
1 stop5h 20m
Southwest
Deal found 5/19![Southwest logo]()
$256
This United Airlines deal was found by Cheapflights users on 5/18. 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 7/36:05 pm
DRO
- ORD
1 stop5h 39m
United Airlines
Sun 7/55:00 am
ORD
- DRO
1 stop5h 33m
United Airlines
Deal found 5/18![United Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 5/16. 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 7/15:06 pm
DRO
- ORD
1 stop6h 33m
American Airlines
Wed 7/85:00 am
ORD
- DRO
1 stop5h 51m
American Airlines
Deal found 5/16![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 5/16. 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.
Wed 5/2710:27 am
DEN
- ORD
1 stop5h 02m
Delta
Fri 5/2911:09 am
ORD
- DEN
1 stop7h 05m
Delta
Deal found 5/16![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 5/19. 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 6/268:50 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 6/309:05 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 5/19![Southwest logo]()
$261
This United Airlines deal was found by Cheapflights users on 5/15. 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 6/95:15 am
DRO
- ORD
1 stop5h 08m
United Airlines
Tue 6/165:00 am
ORD
- DRO
1 stop5h 33m
United Airlines
Deal found 5/15![United Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 7/1410:36 pm
DEN
- RFD
1 stop20h 23m
Multiple Airlines
Sun 7/199:19 am
RFD
- DEN
1 stop5h 56m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 5/16. 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 7/36:50 pm
GJT
- MDW
2 stops13h 24m
Delta
Wed 7/89:49 am
MDW
- GJT
2 stops9h 28m
Delta
Deal found 5/16![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 5/18. 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 7/108:50 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 7/135:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 5/18![Southwest logo]()
$265
Last-minute flights from Colorado to ChicagoDiscover last-minute flight deals from Colorado to Chicago. Data last updated May 20, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado to Chicago. Data last updated May 20, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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 6/99:06 pm
DEN
- ORD
1 stop26h 42m
Frontier
Fri 6/129:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/19![Frontier logo]()
$191
This Frontier deal was found by Cheapflights users on 5/16. 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 6/1211:46 pm
DEN
- ORD
1 stop7h 17m
Frontier
Fri 6/199:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/16![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Fri 6/129:58 am
DEN
- ORD
1 stop8h 52m
Frontier
Sat 6/209:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/18![Frontier logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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.
Sat 6/135:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 6/174:59 pm
ORD
- DEN
1 stop16h 21m
Frontier
Deal found 5/19![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/157:26 pm
DEN
- ORD
1 stop8h 41m
Frontier
Fri 6/199:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/18![Frontier logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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 6/165:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Tue 6/239:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/19![Frontier logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 5/18. 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.
Sat 6/205:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Tue 6/231:29 pm
ORD
- DEN
1 stop9h 47m
Frontier
Deal found 5/18![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 5/17. 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.
Sat 6/275:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 7/119:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 5/17![Frontier logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 5/17. 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.
Sat 6/2711:46 pm
DEN
- ORD
1 stop7h 17m
Frontier
Thu 7/29:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 5/17![Frontier logo]()
$186
This Cheapflightsfares deal was found by Cheapflights users on 5/18. 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 6/306:30 am
DEN
- ORD
1 stop12h 20m
Frontier
Tue 7/75:46 pm
ORD
- DEN
1 stop15h 28m
Frontier
Deal found 5/18![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 5/16. 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.
Tue 6/3011:46 pm
DEN
- ORD
1 stop7h 17m
Frontier
Tue 7/141:50 pm
ORD
- DEN
1 stop9h 15m
Frontier
Deal found 5/16![Frontier logo]()
$190
This Priceline deal was found by Cheapflights users on 5/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3011:46 pm
DEN
- MDW
1 stop10h 23m
Frontier
Tue 7/712:11 pm
MDW
- DEN
1 stop10h 54m
Frontier
Deal found 5/18![Frontier 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 May 20, 2026.
Search for one-way flight options from Colorado to Chicago. Find affordable one-way fares based on user searches. Data last updated May 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/15. 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.
Sat 6/135:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 5/15![Frontier logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 8/46:30 am
DEN
- ORD
1 stop12h 23m
Frontier
Deal found 5/19![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 6/106:30 am
DEN
- MDW
1 stop14h 41m
Frontier
Deal found 5/19![Frontier logo]()
$90
This Super.com deal was found by Cheapflights users on 5/15. 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.
Wed 6/247:26 pm
DEN
- ORD
1 stop8h 41m
Frontier
Deal found 5/15![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 5/18. 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.
Wed 7/2911:46 pm
DEN
- ORD
1 stop7h 07m
Frontier
Deal found 5/18![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 6/96:30 am
DEN
- ORD
1 stop12h 23m
Frontier
Deal found 5/19![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 5/20. 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.
Tue 8/186:30 am
DEN
- MDW
1 stop27h 39m
Frontier
Deal found 5/20![Frontier logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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.
Wed 7/157:26 pm
DEN
- ORD
1 stop9h 02m
Frontier
Deal found 5/19![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 5/15. 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.
Wed 7/110:29 pm
DEN
- ORD
1 stop29h 38m
Frontier
Deal found 5/15![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 5/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/185:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 5/20![Frontier logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 5/20. 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.
Wed 6/105:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 5/20![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 6/155:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 5/19![Frontier logo]()
$100
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 May 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $181 (Cheapflightsfares) |
One-way from | $87 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $270 |
Good round-trip deal | $293 or less |
Good one-way deal | $150 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 2,558,603 searches. Data last updated May 20, 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 - MDW
DENMDW
Denver Intl
Wed 7/8
7:00 pm-10:25 pm
Nonstop2h 25m
Chicago Midway
Tue 7/14
9:05 pm-10:50 pm
Nonstop2h 45m
$217
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 8/5
9:05 pm-12:44 am
Nonstop2h 39m
Chicago O'Hare Intl
Sat 8/8
6:00 am-7:41 am
Nonstop2h 41m
$227
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 8/5
1:55 pm-7:25 pm
1 stop4h 30m
Chicago Midway
Mon 8/10
8:45 pm-10:20 pm
Nonstop2h 35m
$233
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Mon 10/5
5:55 am-9:15 am
Nonstop2h 20m
Chicago Midway
Thu 10/8
6:00 am-7:40 am
Nonstop2h 40m
$237
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 8/5
7:25 pm-10:50 pm
Nonstop2h 25m
Chicago Midway
Sat 8/8
1:45 pm-6:40 pm
1 stop5h 55m
$237
DenverChicago
DEN - ORD
DENORD
Denver Intl
Tue 7/14
7:10 pm-10:49 pm
Nonstop2h 39m
Chicago O'Hare Intl
Sat 7/18
7:05 am-8:55 am
Nonstop2h 50m
$241
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 6/24
9:05 pm-12:44 am
Nonstop2h 39m
Chicago O'Hare Intl
Mon 6/29
5:00 am-6:41 am
Nonstop2h 41m
$241
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 10/8
5:55 am-9:15 am
Nonstop2h 20m
Chicago Midway
Mon 10/12
5:00 am-8:55 am
1 stop4h 55m
$243
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 8/5
12:59 am-7:56 am
1 stop5h 57m
Chicago O'Hare Intl
Tue 8/11
6:25 am-12:06 pm
1 stop6h 41m
$247
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 7/22
10:15 am-4:50 pm
1 stop5h 35m
Chicago Midway
Mon 7/27
5:15 am-6:50 am
Nonstop2h 35m
$251
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
DEN-RFD
ASE-ORD
COS-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
DEN-RFD
ASE-ORD
What is the cheapest month to book a flight from Colorado to Chicago?
Currently, August is the cheapest month in which you can book a flight from Colorado to Chicago (average of $224). Flying from Colorado to Chicago in December is currently the most expensive (average of $414). 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 May 20, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 59% 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 May 20, 2026.
The most flights from USCO to CHI are scheduled on a Wednesday (76 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Colorado to Chicago?
How far ahead should I book a flight from Colorado to Chicago?
Booking 78 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 May 16, 2026.
Travelers seeking maximum savings on their Colorado to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday at noon 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
Lansing
Merrillville
Hammond
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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Complete your trip
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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 May 20, 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 May 20, 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 2,558,603 searches. Data last updated May 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$75 | Average$186 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$316 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$164 | Average$408 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$174 | Average$455 | FlexibilityNo cancel fee | On-time69% |