$89+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
May 9 — May 161
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 April 9, 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 April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 4/246:30 am
DEN
- ORD
1 stop9h 30m
Frontier
Sat 4/255:50 am
ORD
- DEN
1 stop7h 24m
Frontier
Deal found 4/4![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 4/4. 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 4/237:05 pm
DEN
- ORD
1 stop10h 03m
Frontier
Sat 4/255:50 am
ORD
- DEN
1 stop7h 24m
Frontier
Deal found 4/4![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/67:15 am
DEN
- MDW
2 stops13h 47m
Frontier
Wed 5/133:07 pm
MDW
- DEN
1 stop16h 26m
Frontier
Deal found 4/5![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 5/159:06 pm
DEN
- ORD
1 stop24h 55m
Frontier
Mon 5/189:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Deal found 4/6![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 4/5. 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 5/811:54 pm
DEN
- MDW
1 stop10h 10m
Frontier
Wed 5/1312:04 pm
MDW
- DEN
1 stop11h 20m
Frontier
Deal found 4/5![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 4/7. 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 5/311:59 pm
DEN
- ORD
1 stop10h 33m
Frontier
Tue 5/51:59 pm
ORD
- DEN
1 stop9h 25m
Frontier
Deal found 4/7![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 4/6. 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 4/271:07 pm
DEN
- MDW
1 stop8h 12m
Frontier
Sat 5/29:14 am
MDW
- DEN
1 stop14h 45m
Frontier
Deal found 4/6![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 4/5. 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 4/119:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Fri 4/1710:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Deal found 4/5![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 4/7. 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.
Wed 4/221:09 pm
DEN
- MDW
1 stop8h 05m
Frontier
Sat 4/259:14 am
MDW
- DEN
1 stop14h 45m
Frontier
Deal found 4/7![Frontier logo]()
$182
This Super.com deal was found by Cheapflights users on 4/6. 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 5/214:54 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sun 5/249:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Deal found 4/6![Frontier logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 5/159:06 pm
DEN
- ORD
1 stop24h 55m
Frontier
Thu 5/216:55 am
ORD
- DEN
1 stop8h 09m
Frontier
Deal found 4/6![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/57:30 am
DEN
- MDW
2 stops13h 32m
Frontier
Sat 5/93:07 pm
MDW
- DEN
1 stop6h 36m
Frontier
Deal found 4/6![Frontier logo]()
$184
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 April 9, 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 April 9, 2026.
This Southwest deal was found by Cheapflights users on 4/8. 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 5/66:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Wed 5/136:30 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 4/8![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 4/5. 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 5/209:06 am
DEN
- ORD
1 stop6h 45m
Delta
Fri 5/228:05 pm
ORD
- DEN
1 stop4h 36m
Delta
Deal found 4/5![Delta logo]()
$243
This United Airlines deal was found by Cheapflights users on 4/8. 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 5/79:20 pm
DEN
- ORD
Nonstop2h 38m
United Airlines
Sat 5/910:49 am
ORD
- DEN
Nonstop2h 56m
United Airlines
Deal found 4/8![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 4/4. 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 4/305:04 pm
DRO
- ORD
1 stop5h 44m
American Airlines
Sun 5/35:00 am
ORD
- DRO
1 stop7h 11m
American Airlines
Deal found 4/4![American Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 4/4. 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 6/26:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Sat 6/62:15 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 4/4![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 4/8. 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 5/76:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Sat 5/95:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 4/8![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 4/6. 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.
Mon 7/66:00 am
DEN
- ORD
1 stop4h 31m
Delta
Thu 7/95:54 pm
ORD
- DEN
1 stop6h 33m
Delta
Deal found 4/6![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 4/5. 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 4/299:20 am
DEN
- ORD
1 stop8h 30m
Southwest
Thu 4/306:15 pm
ORD
- DEN
Nonstop2h 50m
Southwest
Deal found 4/5![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 4/6. 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 5/88:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 5/126:30 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 4/6![Southwest logo]()
$223
This United Airlines deal was found by Cheapflights users on 4/8. 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 7/96:10 pm
GJT
- ORD
1 stop5h 34m
United Airlines
Fri 7/175:00 am
ORD
- GJT
1 stop4h 53m
United Airlines
Deal found 4/8![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 4/6. 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 5/1311:45 am
DEN
- MDW
1 stop3h 55m
Southwest
Fri 5/155:15 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 4/6![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 4/5. 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 7/96:56 pm
GJT
- ORD
2 stops12h 03m
Delta
Tue 7/142:07 pm
ORD
- GJT
2 stops8h 43m
Delta
Deal found 4/5![Delta logo]()
$309
This United Airlines deal was found by Cheapflights users on 4/8. 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 8/2012:50 pm
MTJ
- ORD
Nonstop2h 59m
United Airlines
Sat 8/229:00 am
ORD
- MTJ
Nonstop3h 26m
United Airlines
Deal found 4/8![United Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 4/9. 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 4/234:58 pm
GJT
- ORD
1 stop5h 50m
American Airlines
Sun 4/265:00 am
ORD
- GJT
1 stop8h 12m
American Airlines
Deal found 4/9![American Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 4/8. 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 5/95:45 pm
DEN
- MDW
Nonstop2h 35m
Southwest
Sun 5/106:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 4/8![Southwest logo]()
$231
This United Airlines deal was found by Cheapflights users on 4/7. 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 8/2712:50 pm
MTJ
- ORD
Nonstop2h 59m
United Airlines
Mon 8/319:00 am
ORD
- MTJ
Nonstop3h 26m
United Airlines
Deal found 4/7![United Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 4/4. 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 6/47:05 pm
DEN
- MDW
1 stop4h 55m
Southwest
Mon 6/89:25 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 4/4![Southwest logo]()
$231
This United Airlines deal was found by Cheapflights users on 4/4. 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 5/2812:31 pm
MTJ
- ORD
Nonstop3h 18m
United Airlines
Fri 6/59:04 am
ORD
- MTJ
Nonstop3h 39m
United Airlines
Deal found 4/4![United Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 4/8. 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 5/2011:55 am
COS
- ORD
1 stop5h 55m
Delta
Fri 5/2911:09 am
ORD
- COS
2 stops11h 18m
Delta
Deal found 4/8![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 4/4. 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 5/162:25 pm
DEN
- ORD
1 stop8h 00m
Southwest
Tue 5/1911:55 am
ORD
- DEN
2 stops8h 30m
Southwest
Deal found 4/4![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 4/6. 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 4/297:45 am
GJT
- ORD
2 stops12h 40m
Delta
Sat 5/27:10 am
ORD
- GJT
2 stops12h 25m
Delta
Deal found 4/6![Delta logo]()
$370
This United Airlines deal was found by Cheapflights users on 4/8. 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 5/811:43 am
COS
- ORD
Nonstop2h 44m
United Airlines
Sun 5/108:46 am
ORD
- COS
Nonstop3h 01m
United Airlines
Deal found 4/8![United Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 4/5. 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 6/198:50 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 6/225:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 4/5![Southwest logo]()
$245
This American Airlines deal was found by Cheapflights users on 4/5. 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 6/186:00 am
DRO
- ORD
1 stop5h 43m
American Airlines
Tue 6/236:48 pm
ORD
- DRO
1 stop6h 16m
American Airlines
Deal found 4/5![American Airlines logo]()
$480
This Delta deal was found by Cheapflights users on 4/5. 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 5/201:55 pm
COS
- MDW
1 stop6h 14m
Delta
Fri 5/291:22 pm
MDW
- COS
2 stops10h 00m
Delta
Deal found 4/5![Delta logo]()
$370
This United Airlines deal was found by Cheapflights users on 4/5. 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 5/21:25 pm
COS
- ORD
1 stop6h 58m
United Airlines
Tue 5/57:50 pm
ORD
- COS
Nonstop3h 11m
United Airlines
Deal found 4/5![United Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 4/8. 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 5/71:00 pm
DEN
- ORD
2 stops9h 55m
Southwest
Sat 5/92:05 pm
ORD
- DEN
2 stops9h 15m
Southwest
Deal found 4/8![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 4/5. 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 8/251:40 pm
COS
- MDW
1 stop7h 06m
Delta
Fri 8/2810:35 am
MDW
- COS
2 stops12h 54m
Delta
Deal found 4/5![Delta logo]()
$378
This Southwest deal was found by Cheapflights users on 4/7. 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 4/296:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Sun 5/36:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 4/7![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 4/5. 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 5/13:13 pm
EGE
- ORD
1 stop6h 45m
United Airlines
Sun 5/37:00 am
ORD
- EGE
1 stop6h 42m
United Airlines
Deal found 4/5![United Airlines logo]()
$369
Last-minute flights from Colorado to ChicagoDiscover last-minute flight deals from Colorado to Chicago. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado to Chicago. Data last updated April 9, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/5. 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 4/1411:59 pm
DEN
- ORD
1 stop9h 03m
Frontier
Fri 5/18:58 pm
ORD
- DEN
1 stop8h 01m
Frontier
Deal found 4/5![Frontier logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 4/4. 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 4/181:09 pm
DEN
- ORD
1 stop8h 30m
Frontier
Sun 4/195:59 am
ORD
- DEN
1 stop7h 10m
Frontier
Deal found 4/4![Frontier logo]()
$179
This Expedia deal was found by Cheapflights users on 4/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:09 pm
DEN
- ORD
1 stop8h 30m
Frontier
Tue 4/2110:45 am
ORD
- DEN
1 stop12h 44m
Frontier
Deal found 4/4![Frontier logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 4/4. 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 4/181:09 pm
DEN
- ORD
1 stop8h 30m
Frontier
Mon 4/2010:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Deal found 4/4![Frontier logo]()
$183
This Trip.com deal was found by Cheapflights users on 4/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:09 pm
DEN
- MDW
1 stop8h 05m
Frontier
Thu 4/232:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Deal found 4/4![Frontier logo]()
$186
This Frontier deal was found by Cheapflights users on 4/7. 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.
Wed 4/221:09 pm
DEN
- MDW
1 stop8h 05m
Frontier
Sat 4/259:14 am
MDW
- DEN
1 stop14h 45m
Frontier
Deal found 4/7![Frontier logo]()
$182
This Trip.com deal was found by Cheapflights users on 4/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/241:09 pm
DEN
- MDW
1 stop8h 17m
Frontier
Wed 4/292:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Deal found 4/6![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 4/6. 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 4/271:07 pm
DEN
- MDW
1 stop8h 12m
Frontier
Sat 5/29:14 am
MDW
- DEN
1 stop14h 45m
Frontier
Deal found 4/6![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/57:30 am
DEN
- MDW
2 stops13h 32m
Frontier
Sat 5/93:07 pm
MDW
- DEN
1 stop6h 36m
Frontier
Deal found 4/6![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/67:15 am
DEN
- MDW
2 stops13h 47m
Frontier
Wed 5/133:07 pm
MDW
- DEN
1 stop16h 26m
Frontier
Deal found 4/5![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 4/5. 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 5/811:54 pm
DEN
- MDW
1 stop10h 10m
Frontier
Wed 5/1312:04 pm
MDW
- DEN
1 stop11h 20m
Frontier
Deal found 4/5![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 4/5. 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 5/197:00 am
DEN
- MDW
1 stop6h 12m
Frontier
Sun 5/246:00 am
MDW
- DEN
1 stop9h 04m
Frontier
Deal found 4/5![Frontier logo]()
$185
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 April 9, 2026.
Search for one-way flight options from Colorado to Chicago. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 4/241:09 pm
DEN
- ORD
1 stop8h 30m
Frontier
Deal found 4/8![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 4/7. 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.
Fri 4/241:09 pm
DEN
- MDW
1 stop8h 17m
Frontier
Deal found 4/7![Frontier logo]()
$89
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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.
Sun 5/1711:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 4/6![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 4/6. 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 5/185:05 am
DEN
- MDW
1 stop8h 07m
Frontier
Deal found 4/6![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 5/111:59 pm
DEN
- ORD
1 stop20h 13m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$91
This Frontier deal was found by Cheapflights users on 4/8. 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 5/811:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 4/8![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 6/35:05 am
DEN
- ORD
1 stop8h 58m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 6/111:54 pm
DEN
- MDW
1 stop10h 18m
Frontier
Deal found 4/4![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 4/4. 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 4/236:00 am
DEN
- ORD
1 stop23h 20m
Frontier
Deal found 4/4![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 4/4. 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 5/1711:54 pm
DEN
- MDW
1 stop10h 15m
Frontier
Deal found 4/4![Frontier logo]()
$94
This Frontier deal was found by Cheapflights users on 4/6. 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.
Wed 6/1011:42 pm
DEN
- ORD
1 stop7h 21m
Frontier
Deal found 4/6![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/309:00 pm
DEN
- MDW
1 stop23h 37m
Frontier
Deal found 4/6![Frontier logo]()
$95
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 April 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $178 (Kiwi.com) |
One-way from | $89 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $262 |
Good round-trip deal | $229 or less |
Good one-way deal | $149 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 April 9, 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 5/6
6:35 am-9:55 am
Nonstop2h 20m
Chicago Midway
Wed 5/13
6:30 am-8:10 am
Nonstop2h 40m
$201
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 6/2
6:35 am-9:55 am
Nonstop2h 20m
Chicago Midway
Sat 6/6
2:15 pm-3:55 pm
Nonstop2h 40m
$211
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 5/7
6:35 am-9:55 am
Nonstop2h 20m
Chicago Midway
Sat 5/9
5:30 pm-7:10 pm
Nonstop2h 40m
$219
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 4/29
9:20 am-6:50 pm
1 stop8h 30m
Chicago O'Hare Intl
Thu 4/30
6:15 pm-8:05 pm
Nonstop2h 50m
$221
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 5/8
8:20 pm-11:40 pm
Nonstop2h 20m
Chicago Midway
Tue 5/12
6:30 am-8:10 am
Nonstop2h 40m
$223
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 5/13
11:45 am-4:40 pm
1 stop3h 55m
Chicago Midway
Fri 5/15
5:15 pm-6:55 pm
Nonstop2h 40m
$229
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 5/9
5:45 pm-9:20 pm
Nonstop2h 35m
Chicago Midway
Sun 5/10
6:00 am-7:40 am
Nonstop2h 40m
$231
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 6/4
7:05 pm-1:00 am
1 stop4h 55m
Chicago Midway
Mon 6/8
9:25 pm-11:05 pm
Nonstop2h 40m
$231
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 5/16
2:25 pm-11:25 pm
1 stop8h 00m
Chicago O'Hare Intl
Tue 5/19
11:55 am-7:25 pm
2 stops8h 30m
$234
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 5/20
9:06 am-4:51 pm
1 stop6h 45m
Chicago O'Hare Intl
Fri 5/22
8:05 pm-11:41 pm
1 stop4h 36m
$243
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-ORD
DRO-ORD
GJT-ORD
MTJ-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-MDW
DEN-ORD
DRO-ORD
GJT-ORD
What is the cheapest month to book a flight from Colorado to Chicago?
Currently, December is the cheapest month in which you can book a flight from Colorado to Chicago (average of $86). Flying from Colorado to Chicago in March is currently the most expensive (average of $170). 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 April 9, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 61% on flights from Colorado to Chicago by exploring options for tickets in the evening.
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 April 4, 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. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 9, 2026.
The most flights from USCO to CHI are scheduled on a Wednesday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 on average).
How much does it cost to fly round-trip from Colorado to Chicago?
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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 April 9, 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 April 9, 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 April 9, 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$155 | Average$300 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$413 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$164 | Average$439 | FlexibilityNo cancel fee | On-time69% |