$103+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Aug 23 — Aug 301
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 July 24, 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 July 24, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/24. 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 8/189:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Sat 8/222:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/24![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Sat 8/2910:43 am
DEN
- ORD
1 stop8h 25m
Frontier
Wed 9/22:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/22![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Thu 9/32:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/22![Frontier logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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.
Fri 9/186:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Sun 9/2011:06 am
ORD
- DEN
Nonstop2h 54m
Frontier
Deal found 7/22![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Tue 8/187:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Mon 8/242:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/23![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Thu 8/208:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Sun 8/233:59 pm
RFD
- DEN
1 stop24h 02m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Thu 8/206:22 am
DEN
- ORD
1 stop17h 27m
Frontier
Thu 8/272:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/21![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Sat 8/155:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Fri 8/212:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/23![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Thu 9/108:44 pm
DEN
- ORD
1 stop23h 50m
Frontier
Tue 9/152:46 pm
ORD
- DEN
1 stop10h 07m
Frontier
Deal found 7/22![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:10 pm
DEN
- ORD
1 stop13h 10m
Frontier
Sat 9/266:30 am
ORD
- DEN
Nonstop2h 45m
Frontier
Deal found 7/24![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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.
Fri 8/145:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Wed 8/192:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/19![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Fri 8/2111:59 pm
DEN
- ORD
1 stop6h 54m
Frontier
Sun 8/237:05 am
ORD
- DEN
1 stop7h 56m
Frontier
Deal found 7/20![Frontier logo]()
$181
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 July 24, 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 July 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Thu 8/278:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Sun 8/309:35 pm
RFD
- DEN
1 stop7h 13m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$203
This Southwest deal was found by Cheapflights users on 7/20. 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 8/117:25 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 8/188:20 am
MDW
- DEN
1 stop5h 00m
Southwest
Deal found 7/20![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 7/23. 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.
Tue 9/158:45 am
DEN
- ORD
1 stop7h 14m
Delta
Wed 9/165:10 pm
ORD
- DEN
1 stop5h 22m
Delta
Deal found 7/23![Delta logo]()
$225
This United Airlines deal was found by Cheapflights users on 7/19. 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.
Wed 10/214:40 pm
DEN
- ORD
Nonstop2h 42m
United Airlines
Sat 10/2410:00 pm
ORD
- DEN
Nonstop2h 54m
United Airlines
Deal found 7/19![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 7/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:47 pm
DRO
- ORD
1 stop6h 27m
American Airlines
Mon 9/145:00 am
ORD
- DRO
1 stop5h 48m
American Airlines
Deal found 7/19![American Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 7/21. 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.
Mon 9/75:00 am
DEN
- MDW
Nonstop2h 25m
Southwest
Thu 9/1012:05 pm
MDW
- DEN
1 stop4h 55m
Southwest
Deal found 7/21![Southwest logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/208:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Sun 8/233:59 pm
RFD
- DEN
1 stop24h 02m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 7/23. 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.
Tue 9/156:30 am
DEN
- MDW
1 stop5h 09m
Delta
Wed 9/167:13 pm
MDW
- DEN
1 stop5h 22m
Delta
Deal found 7/23![Delta logo]()
$225
This Southwest deal was found by Cheapflights users on 7/21. 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 8/2211:10 am
DEN
- MDW
1 stop5h 00m
Southwest
Tue 8/2511:10 am
MDW
- DEN
1 stop4h 50m
Southwest
Deal found 7/21![Southwest logo]()
$216
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Tue 8/2511:55 am
COS
- ORD
Nonstop2h 43m
United Airlines
Tue 9/86:00 am
ORD
- COS
1 stop5h 44m
United Airlines
Deal found 7/21![United Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Thu 10/156:30 am
DEN
- RFD
2 stops12h 43m
Multiple Airlines
Sun 10/181:12 pm
RFD
- DEN
1 stop24h 32m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$243
This Delta deal was found by Cheapflights users on 7/19. 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 10/216:10 am
DEN
- ORD
1 stop5h 51m
Delta
Sat 10/249:59 am
ORD
- DEN
1 stop6h 50m
Delta
Deal found 7/19![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 7/21. 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.
Tue 9/16:00 am
DEN
- MDW
1 stop5h 00m
Southwest
Tue 9/11:55 pm
MDW
- DEN
2 stops6h 55m
Southwest
Deal found 7/21![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Tue 9/1511:55 am
COS
- ORD
Nonstop2h 43m
United Airlines
Wed 9/165:00 am
ORD
- COS
1 stop4h 40m
United Airlines
Deal found 7/22![United Airlines logo]()
$253
This Delta deal was found by Cheapflights users on 7/20. 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 8/136:05 am
DEN
- MDW
1 stop5h 34m
Delta
Mon 8/171:25 pm
MDW
- DEN
1 stop4h 58m
Delta
Deal found 7/20![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/266:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 8/318:15 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/20![Southwest logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Thu 9/1010:29 am
DEN
- RFD
1 stop9h 10m
Multiple Airlines
Sun 9/139:29 pm
RFD
- DEN
1 stop7h 23m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$252
This American Airlines deal was found by Cheapflights users on 7/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:40 pm
DRO
- ORD
1 stop6h 50m
American Airlines
Mon 8/315:00 am
ORD
- DRO
1 stop8h 00m
American Airlines
Deal found 7/19![American Airlines logo]()
$308
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Tue 12/298:00 am
COS
- ORD
Nonstop2h 34m
United Airlines
Tue 1/55:00 am
ORD
- COS
1 stop5h 05m
United Airlines
Deal found 7/21![United Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:47 pm
DRO
- ORD
1 stop6h 31m
American Airlines
Sat 9/51:40 pm
ORD
- DRO
1 stop8h 34m
American Airlines
Deal found 7/21![American Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 7/23. 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 10/812:59 am
DEN
- ORD
1 stop6h 04m
Delta
Tue 10/136:30 am
ORD
- DEN
1 stop4h 27m
Delta
Deal found 7/23![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 7/19. 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 8/2211:10 am
DEN
- MDW
1 stop5h 00m
Southwest
Mon 8/245:00 pm
MDW
- DEN
1 stop3h 50m
Southwest
Deal found 7/19![Southwest logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Fri 9/117:00 am
DEN
- RFD
1 stop10h 11m
Multiple Airlines
Sun 9/133:53 pm
RFD
- DEN
1 stop6h 56m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$276
This United Airlines deal was found by Cheapflights users on 7/20. 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 8/2012:40 pm
MTJ
- ORD
Nonstop3h 10m
United Airlines
Mon 8/249:15 am
ORD
- MTJ
Nonstop3h 33m
United Airlines
Deal found 7/20![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 7/22. 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.
Thu 10/812:59 am
DEN
- ORD
1 stop6h 04m
Delta
Thu 10/152:00 pm
ORD
- DEN
1 stop8h 15m
Delta
Deal found 7/22![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 7/21. 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 9/256:30 pm
DEN
- MDW
Nonstop2h 30m
Southwest
Mon 9/284:10 pm
MDW
- DEN
1 stop4h 40m
Southwest
Deal found 7/21![Southwest logo]()
$250
This American Airlines deal was found by Cheapflights users on 7/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:54 pm
ASE
- ORD
Nonstop3h 13m
American Airlines
Sun 8/236:45 pm
ORD
- ASE
Nonstop3h 10m
American Airlines
Deal found 7/19![American Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 7/20. 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 9/312:59 am
DEN
- ORD
1 stop5h 57m
Delta
Sun 9/66:00 am
ORD
- DEN
1 stop4h 59m
Delta
Deal found 7/20![Delta logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 9/38:31 am
DEN
- RFD
1 stop5h 32m
Multiple Airlines
Sun 9/69:29 pm
RFD
- DEN
2 stops35h 14m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 7/24. 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.
Sat 10/106:00 am
DEN
- ORD
Nonstop2h 43m
United Airlines
Sat 10/171:30 pm
ORD
- DEN
Nonstop2h 47m
United Airlines
Deal found 7/24![United Airlines logo]()
$296
Last-minute flights from Colorado to ChicagoDiscover last-minute flight deals from Colorado to Chicago. Data last updated July 24, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado to Chicago. Data last updated July 24, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/21. 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.
Mon 8/35:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 8/119:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/21![Frontier logo]()
$198
This Southwest deal was found by Cheapflights users on 7/21. 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.
Thu 8/1311:00 am
DEN
- MDW
1 stop5h 00m
Southwest
Mon 8/177:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/21![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 7/22. 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.
Sat 8/1511:10 am
DEN
- MDW
1 stop5h 00m
Southwest
Tue 8/181:55 pm
MDW
- DEN
2 stops6h 55m
Southwest
Deal found 7/22![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 7/22. 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 8/1811:15 am
DEN
- MDW
1 stop4h 45m
Southwest
Tue 8/258:20 am
MDW
- DEN
1 stop5h 00m
Southwest
Deal found 7/22![Southwest logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Thu 8/208:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Sun 8/233:59 pm
RFD
- DEN
1 stop24h 02m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Thu 8/208:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Mon 8/246:56 pm
RFD
- DEN
2 stops28h 09m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 7/21. 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.
Thu 8/203:15 pm
DEN
- MDW
1 stop3h 30m
Southwest
Thu 8/2712:05 pm
MDW
- DEN
1 stop4h 55m
Southwest
Deal found 7/21![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 7/22. 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.
Sat 8/227:15 am
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 8/256:00 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/22![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 7/21. 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 8/2211:10 am
DEN
- MDW
1 stop5h 00m
Southwest
Sat 9/56:00 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/21![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 7/24. 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 8/226:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Sat 8/296:50 am
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 7/24![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/2611:15 am
DEN
- MDW
1 stop3h 45m
Southwest
Sat 9/56:00 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/20![Southwest logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Thu 8/278:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Sun 8/309:35 pm
RFD
- DEN
1 stop7h 13m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$203
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 July 24, 2026.
Search for one-way flight options from Colorado to Chicago. Find affordable one-way fares based on user searches. Data last updated July 24, 2026.
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 8/136:18 pm
DEN
- ORD
Nonstop2h 42m
United Airlines
Deal found 7/22![United Airlines logo]()
$103
This Southwest deal was found by Cheapflights users on 7/22. 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 8/248:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/22![Southwest logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Thu 10/228:50 am
DEN
- ORD
1 stop11h 44m
Frontier
Deal found 7/22![Frontier logo]()
$106
This American Airlines deal was found by Cheapflights users on 7/24. 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.
Tue 8/185:44 pm
DEN
- ORD
Nonstop3h 01m
American Airlines
Deal found 7/24![American Airlines logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Sat 9/58:31 am
DEN
- RFD
1 stop29h 32m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$107
This Southwest deal was found by Cheapflights users on 7/24. 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.
Mon 9/216:30 pm
DEN
- MDW
Nonstop2h 35m
Southwest
Deal found 7/24![Southwest logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Sat 9/59:21 pm
DEN
- ORD
1 stop26h 28m
Frontier
Deal found 7/23![Frontier logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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.
Thu 8/209:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Deal found 7/19![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Thu 8/278:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$109
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Thu 9/38:29 pm
DEN
- ORD
Nonstop2h 30m
United Airlines
Deal found 7/21![United Airlines logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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.
Mon 8/35:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 7/22![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Sat 9/268:40 am
DEN
- ORD
1 stop11h 54m
Frontier
Deal found 7/23![Frontier logo]()
$112
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 July 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $172 (Kiwi.com) |
One-way from | $103 (United Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $296 |
Good round-trip deal | $269 or less |
Good one-way deal | $162 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 July 24, 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 - RFD
DENRFD
Denver Intl
Thu 8/27
8:31 am-3:09 pm
1 stop5h 38m
Chicago Greater Rockford
Sun 8/30
9:35 pm-3:48 am
1 stop7h 13m
$203
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 8/11
7:25 pm-10:50 pm
Nonstop2h 25m
Chicago Midway
Tue 8/18
8:20 am-12:20 pm
1 stop5h 00m
$211
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Mon 9/7
5:00 am-8:25 am
Nonstop2h 25m
Chicago Midway
Thu 9/10
12:05 pm-4:00 pm
1 stop4h 55m
$215
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 8/22
11:10 am-5:10 pm
1 stop5h 00m
Chicago Midway
Tue 8/25
11:10 am-3:00 pm
1 stop4h 50m
$216
DenverChicago
DEN - RFD
DENRFD
Denver Intl
Thu 8/20
8:31 am-3:09 pm
1 stop5h 38m
Chicago Greater Rockford
Sun 8/23
3:59 pm-3:01 pm
1 stop24h 02m
$222
DenverChicago
DEN - ORD
DENORD
Denver Intl
Tue 9/15
8:45 am-4:59 pm
1 stop7h 14m
Chicago O'Hare Intl
Wed 9/16
5:10 pm-9:32 pm
1 stop5h 22m
$225
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 9/15
6:30 am-12:39 pm
1 stop5h 09m
Chicago Midway
Wed 9/16
7:13 pm-11:35 pm
1 stop5h 22m
$225
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 9/1
6:00 am-12:00 pm
1 stop5h 00m
Chicago Midway
Tue 9/1
1:55 pm-7:50 pm
2 stops6h 55m
$226
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 10/21
4:40 pm-8:22 pm
Nonstop2h 42m
Chicago O'Hare Intl
Sat 10/24
10:00 pm-11:54 pm
Nonstop2h 54m
$227
Quickest round-trip
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 8/26
6:30 am-9:50 am
Nonstop2h 20m
Chicago Midway
Mon 8/31
8:15 pm-9:50 pm
Nonstop2h 35m
$227
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-MDW
DEN-RFD
DEN-ORD
MTJ-ORD
COS-MDW
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-MDW
DEN-RFD
DEN-ORD
MTJ-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 $242). Flying from Colorado to Chicago in June is currently the most expensive (average of $352). 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 July 24, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 58% 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 July 24, 2026.
The most flights from USCO to CHI are scheduled on a Friday (83 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 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 $190 and $338 in August.The cheapest round-trip price found within the last 5 days was $172 on Frontier (Aug 29-Sep 2).
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 July 18, 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
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
Chicago flight 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 July 24, 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 July 24, 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 July 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$193 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$281 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$168 | Average$429 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$169 | Average$340 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$179 | Average$469 | FlexibilityNo cancel fee | On-time69% |