$94+ Cheap flights from Denver (DEN) 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Jul 20 — Jul 271
Round-trip
1 adult, Economy
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Find cheap flights from Denver to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Denver Intl to Chicago are usually found in January or August, booked 79 days in advance, depart on a Friday or Thursday and return on a Wednesday
Cheap flight deals from Denver to Chicago
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Best
Last-minute
One-way
Cheapest flights from Denver to ChicagoExplore the most affordable flight options available from Denver to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 2026.
Explore the most affordable flight options available from Denver to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 2026.
This Super.com deal was found by Cheapflights users on 6/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Sun 8/239:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/16![Frontier logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:15 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sun 8/239:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/15![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Wed 7/15:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Tue 7/149:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/15![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 6/17. 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.
Wed 8/510:00 am
DEN
- ORD
1 stop8h 53m
Frontier
Wed 8/59:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/17![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/147:00 am
DEN
- ORD
1 stop16h 49m
Frontier
Wed 7/229:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/19![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 7/235:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/289:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/16![Frontier logo]()
$186
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 10/106:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Tue 10/136:05 am
ORD
- DEN
1 stop9h 53m
Frontier
Deal found 6/19![Frontier logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/145:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/219:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/19![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 6/17. 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.
Sat 8/155:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 8/186:55 am
ORD
- DEN
1 stop8h 04m
Frontier
Deal found 6/17![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Fri 7/245:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/289:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/17![Frontier logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 8/1210:00 am
DEN
- ORD
1 stop18h 37m
Frontier
Sun 8/169:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/19![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 7/45:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Thu 7/169:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/15![Frontier logo]()
$192
Best flights from Denver to ChicagoDiscover carefully curated flight deals from Denver to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
Discover carefully curated flight deals from Denver to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
This Southwest deal was found by Cheapflights users on 6/19. 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.
Tue 7/146:15 am
DEN
- MDW
Nonstop2h 25m
Southwest
Wed 7/155:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/19![Southwest logo]()
$205
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Thu 10/86:00 am
DEN
- ORD
Nonstop2h 43m
United Airlines
Sat 10/105:51 pm
ORD
- DEN
Nonstop2h 54m
United Airlines
Deal found 6/15![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 6/19. 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.
Sat 9/126:05 am
DEN
- ORD
1 stop5h 58m
Delta
Mon 9/146:15 am
ORD
- DEN
1 stop6h 53m
Delta
Deal found 6/19![Delta logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Fri 9/187:00 am
DEN
- RFD
1 stop10h 11m
Multiple Airlines
Sun 9/209:29 pm
RFD
- DEN
1 stop13h 05m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 6/17. 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 8/56:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 8/113:50 pm
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 6/17![Southwest logo]()
$216
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:05 am
DEN
- ORD
1 stop5h 59m
Delta
Sat 9/128:55 am
ORD
- DEN
1 stop6h 03m
Delta
Deal found 6/15![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 6/19. 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.
Thu 11/56:45 pm
DEN
- MDW
Nonstop2h 15m
Southwest
Mon 11/912:45 pm
MDW
- DEN
1 stop4h 50m
Southwest
Deal found 6/19![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:00 am
DEN
- ORD
1 stop8h 22m
Delta
Mon 9/287:01 am
ORD
- DEN
1 stop7h 50m
Delta
Deal found 6/15![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 6/19. 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.
Mon 7/208:50 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Wed 7/225:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/19![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 6/18. 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.
Sat 8/86:05 am
DEN
- ORD
1 stop6h 45m
Delta
Mon 8/108:48 am
ORD
- DEN
1 stop5h 57m
Delta
Deal found 6/18![Delta logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Thu 9/108:30 am
DEN
- RFD
1 stop11h 09m
Multiple Airlines
Sun 9/133:53 pm
RFD
- DEN
1 stop6h 56m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 6/16. 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.
Fri 9/116:30 pm
DEN
- MDW
Nonstop2h 30m
Southwest
Tue 9/1511:10 am
MDW
- DEN
1 stop4h 50m
Southwest
Deal found 6/16![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 6/19. 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.
Sat 8/86:05 am
DEN
- ORD
1 stop6h 45m
Delta
Tue 8/118:28 am
ORD
- DEN
1 stop4h 40m
Delta
Deal found 6/19![Delta logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 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 6/18![Multiple Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 6/19. 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.
Tue 7/148:10 am
DEN
- MDW
1 stop5h 25m
Southwest
Thu 7/235:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/19![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 6/17. 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.
Fri 12/46:10 am
DEN
- MDW
1 stop4h 41m
Delta
Tue 12/812:30 pm
MDW
- DEN
1 stop4h 26m
Delta
Deal found 6/17![Delta logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/227:56 am
DEN
- RFD
1 stop23h 33m
Multiple Airlines
Thu 7/3011:27 am
RFD
- DEN
2 stops46h 36m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 7/237:05 pm
DEN
- MDW
1 stop5h 00m
Southwest
Tue 7/285:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/16![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 6/19. 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.
Fri 8/1410:19 am
DEN
- MDW
1 stop7h 14m
Delta
Tue 8/187:25 pm
MDW
- DEN
1 stop5h 09m
Delta
Deal found 6/19![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 6/15. 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 10/225:55 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 10/269:55 am
MDW
- DEN
1 stop4h 20m
Southwest
Deal found 6/15![Southwest logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Thu 9/1710:45 pm
DEN
- RFD
1 stop18h 26m
Multiple Airlines
Sun 9/203:53 pm
RFD
- DEN
1 stop6h 56m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 6/16. 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 7/1511:08 am
DEN
- ORD
1 stop7h 22m
Delta
Tue 7/285:54 pm
ORD
- DEN
1 stop6h 33m
Delta
Deal found 6/16![Delta logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 8/39:15 am
DEN
- RFD
1 stop10h 08m
Multiple Airlines
Fri 8/79:24 pm
RFD
- DEN
1 stop23h 23m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$338
This Southwest deal was found by Cheapflights users on 6/18. 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.
Thu 9/103:55 pm
DEN
- MDW
1 stop4h 35m
Southwest
Sun 9/137:55 am
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 6/18![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 6/19. 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.
Tue 7/216:05 am
DEN
- ORD
1 stop5h 58m
Delta
Tue 7/215:54 pm
ORD
- DEN
1 stop6h 33m
Delta
Deal found 6/19![Delta logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Wed 7/297:56 am
DEN
- RFD
1 stop23h 33m
Multiple Airlines
Sun 8/29:19 am
RFD
- DEN
1 stop6h 04m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:05 am
DEN
- ORD
1 stop5h 59m
Delta
Sun 10/45:42 pm
ORD
- DEN
1 stop6h 43m
Delta
Deal found 6/15![Delta logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Wed 7/159:15 am
DEN
- RFD
1 stop9h 44m
Multiple Airlines
Thu 7/169:19 am
RFD
- DEN
1 stop6h 04m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 6/17. 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.
Thu 8/2712:59 am
DEN
- ORD
1 stop5h 57m
Delta
Mon 8/3111:22 am
ORD
- DEN
1 stop7h 01m
Delta
Deal found 6/17![Delta logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Wed 7/159:15 am
DEN
- RFD
1 stop9h 44m
Multiple Airlines
Sun 7/199:19 am
RFD
- DEN
1 stop6h 04m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$377
Last-minute flights from Denver to ChicagoDiscover last-minute flight deals from Denver to Chicago. Data last updated June 20, 2026 and is based on user searches.
Discover last-minute flight deals from Denver to Chicago. Data last updated June 20, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Wed 7/15:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Tue 7/149:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/15![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 7/45:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Thu 7/169:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/15![Frontier logo]()
$192
This Southwest deal was found by Cheapflights users on 6/16. 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 7/86:10 am
DEN
- MDW
1 stop4h 45m
Southwest
Tue 7/145:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/16![Southwest logo]()
$215
This Super.com deal was found by Cheapflights users on 6/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Sun 8/239:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/16![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Tue 7/147:00 am
DEN
- ORD
1 stop16h 49m
Frontier
Wed 7/229:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/16![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/145:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/219:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/19![Frontier logo]()
$188
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/146:15 am
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 7/217:00 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/16![Southwest logo]()
$205
This Frontier deal was found by Cheapflights users on 6/16. 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.
Wed 7/155:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/219:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/16![Frontier logo]()
$187
This Frontier deal was found by Cheapflights users on 6/16. 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.
Sat 7/185:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Wed 8/51:50 pm
ORD
- DEN
1 stop9h 15m
Frontier
Deal found 6/16![Frontier logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/215:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/289:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/17![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 7/235:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/289:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/16![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Fri 7/245:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/289:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/17![Frontier logo]()
$190
One-way flights from Denver to ChicagoSearch for one-way flight options from Denver to Chicago. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
Search for one-way flight options from Denver to Chicago. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Wed 9/95:56 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Deal found 6/15![Frontier logo]()
$94
This United Airlines deal was found by Cheapflights users on 6/15. 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 7/216:00 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 6/15![United Airlines logo]()
$103
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/146:15 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 6/16![Southwest logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 6/20. 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.
Sat 7/45:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/20![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/411:46 pm
DEN
- MDW
1 stop9h 05m
Frontier
Deal found 6/17![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 6/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
DEN
- ORD
1 stop8h 16m
Frontier
Deal found 6/20![Frontier logo]()
$105
This Priceline deal was found by Cheapflights users on 6/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1211:46 pm
DEN
- MDW
1 stop9h 05m
Frontier
Deal found 6/20![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 6/16. 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 9/155:17 pm
DEN
- ORD
1 stop6h 07m
Frontier
Deal found 6/16![Frontier logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/15![Frontier logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 7/75:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/19![Frontier logo]()
$109
This CheapOair deal was found by Cheapflights users on 6/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:46 pm
DEN
- MDW
1 stop9h 05m
Frontier
Deal found 6/18![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 6/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/19![Frontier logo]()
$111
Find flight deals from Denver to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Denver (DEN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $181 (Super.com) |
One-way from | $94 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $289 |
Good round-trip deal | $287 or less |
Good one-way deal | $145 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Denver 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 June 20, 2026.
Use the filters below to find and compare flights from Denver to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 7/14
6:15 am-9:40 am
Nonstop2h 25m
Chicago Midway
Wed 7/15
5:30 am-7:05 am
Nonstop2h 35m
$205
Quickest round-trip
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 8/5
6:30 am-9:50 am
Nonstop2h 20m
Chicago Midway
Tue 8/11
3:50 pm-5:20 pm
Nonstop2h 30m
$216
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 10/8
6:00 am-9:43 am
Nonstop2h 43m
Chicago O'Hare Intl
Sat 10/10
5:51 pm-7:45 pm
Nonstop2h 54m
$227
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 11/5
6:45 pm-10:00 pm
Nonstop2h 15m
Chicago Midway
Mon 11/9
12:45 pm-4:35 pm
1 stop4h 50m
$233
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Mon 7/20
8:50 pm-12:15 am
Nonstop2h 25m
Chicago Midway
Wed 7/22
5:30 am-7:05 am
Nonstop2h 35m
$235
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 9/12
6:05 am-1:03 pm
1 stop5h 58m
Chicago O'Hare Intl
Mon 9/14
6:15 am-12:08 pm
1 stop6h 53m
$236
DenverChicago
DEN - ORD
DENORD
Denver Intl
Tue 9/8
6:05 am-1:04 pm
1 stop5h 59m
Chicago O'Hare Intl
Sat 9/12
8:55 am-1:58 pm
1 stop6h 03m
$236
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 9/11
6:30 pm-10:00 pm
Nonstop2h 30m
Chicago Midway
Tue 9/15
11:10 am-3:00 pm
1 stop4h 50m
$241
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 7/14
8:10 am-2:35 pm
1 stop5h 25m
Chicago Midway
Thu 7/23
5:15 am-6:50 am
Nonstop2h 35m
$245
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 7/23
7:05 pm-1:05 am
1 stop5h 00m
Chicago Midway
Tue 7/28
5:30 am-7:05 am
Nonstop2h 35m
$245
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from Denver to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Denver to Chicago in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Denver-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Denver-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Denver-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Denver-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Denver-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Denver to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Denver with our price prediction graph.
DEN-CHI
DEN-ORD
DEN-MDW
DEN-RFD
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 Denver to Chicago
DEN-CHI
DEN-ORD
DEN-MDW
DEN-RFD
What is the cheapest month to book a flight from Denver to Chicago?
Currently, September is the cheapest month in which you can book a flight from Denver to Chicago (average of $230). Flying from Denver to Chicago in December is currently the most expensive (average of $490). 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 DEN to CHI?
Find hourly flight availability from Denver 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 June 20, 2026.
It’s optimal to fly from Denver to Chicago in the evening. By choosing this option you can save up to 48% on the cost of your flight, compared to a flight at noon.
Weekly flight availability from Denver to Chicago
Explore weekly flight availability from Denver 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 June 20, 2026.
The most flights from DEN 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 (42 on average).
How much does it cost to fly round-trip from Denver to Chicago?
How far ahead should I book a flight from Denver to Chicago?
The price you pay for your flight from Denver to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 78 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Denver to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Denver to Chicago. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their Denver to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Denver to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Denver to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 20, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Denver to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Denver 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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Alternative routes for Denver 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 June 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 Denver to Chicago by cabin class
Find flights from Denver to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Denver and Chicago flights
Browse other Denver and Chicago flight options. Last updated on June 20, 2026.
Other flights from Denver
Browse through other flights departing from Denver. Flights are based on user searches made on Cheapflights and were last updated on June 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Denver to Chicago
Discover the top 5 airlines that operate flights from Denver 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 June 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$75 | Average$188 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$296 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$168 | Average$281 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$354 | FlexibilityNo cancel fee | On-time69% |