$104+ Cheap flights from Denver (DEN) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Oct 22 — Oct 291
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 December, booked 79 days in advance, depart on a Friday or Thursday and return on a Friday
Cheap flight deals from Denver to Chicago
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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 September 22, 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 September 22, 2026.
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/223:48 pm -
Nonstop2h 34m
Fri 12/2510:41 pm -
Nonstop2h 55m
Deal found 9/16![Frontier logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:40 am -
1 stop8h 49m
Thu 10/228:01 pm -
1 stop23h 00m
Deal found 9/17![Frontier logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 10/228:55 pm -
Nonstop2h 29m
Thu 10/296:30 am -
Nonstop2h 56m
Deal found 9/19![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 9/17. 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.
Thu 10/226:30 am -
1 stop11h 26m
Sat 10/2412:37 pm -
1 stop10h 12m
Deal found 9/17![Frontier logo]()
$173
This Super.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/158:55 pm -
Nonstop2h 29m
Sun 10/186:30 am -
Nonstop2h 49m
Deal found 9/16![Frontier logo]()
$174
This Orbitz deal was found by Cheapflights users on 9/18. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:55 pm -
Nonstop2h 29m
Mon 10/197:44 pm -
1 stop13h 22m
Deal found 9/18![Frontier logo]()
$175
This Super.com deal was found by Cheapflights users on 9/17. 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.
Sat 12/1211:59 pm -
1 stop19h 43m
Tue 12/1512:28 pm -
1 stop8h 27m
Deal found 9/17![Frontier logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 10/218:55 pm -
Nonstop2h 29m
Tue 10/278:13 pm -
1 stop13h 09m
Deal found 9/19![Frontier logo]()
$177
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:05 pm -
1 stop15h 12m
Wed 10/146:30 am -
Nonstop2h 49m
Deal found 9/16![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 10/138:55 pm -
Nonstop2h 29m
Sat 10/176:30 am -
Nonstop2h 49m
Deal found 9/19![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/99:26 pm -
Nonstop2h 28m
Thu 12/1010:37 pm -
1 stop8h 52m
Deal found 9/18![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Sat 10/108:55 pm -
Nonstop2h 29m
Tue 10/138:30 am -
1 stop14h 19m
Deal found 9/17![Frontier logo]()
$181
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 September 22, 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 September 22, 2026.
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:10 pm -
Nonstop2h 42m
Sat 10/107:00 am -
Nonstop2h 47m
Deal found 9/16![United Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 9/21. 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 10/297:50 am -
Nonstop2h 20m
Mon 11/210:40 am -
Nonstop2h 45m
Deal found 9/21![Southwest logo]()
$243
This Cheapflightsfares deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1911:55 pm -
1 stop24h 14m
Sun 1/38:43 pm -
Nonstop3h 01m
Deal found 9/21![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 11/510:37 pm -
1 stop10h 56m
Sun 11/88:37 pm -
1 stop28h 12m
Deal found 9/17![Multiple Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:05 am -
1 stop4h 35m
Sat 11/76:20 am -
1 stop4h 42m
Deal found 9/21![Delta logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 9/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:35 am -
1 stop27h 40m
Tue 12/83:19 pm -
2 stops22h 37m
Deal found 9/19![Alaska Airlines logo]()
$518
This Southwest deal was found by Cheapflights users on 9/21. 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 11/94:30 pm -
Nonstop2h 15m
Fri 11/135:40 pm -
Nonstop2h 45m
Deal found 9/21![Southwest logo]()
$260
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:40 pm -
Nonstop2h 42m
Sun 10/186:00 am -
Nonstop2h 39m
Deal found 9/16![United Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 9/18. 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.
Tue 12/84:10 pm -
1 stop4h 25m
Sun 12/136:20 am -
1 stop7h 01m
Deal found 9/18![Delta logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/2910:37 pm -
1 stop11h 50m
Sun 11/18:53 pm -
2 stops21h 58m
Deal found 9/21![Multiple Airlines logo]()
$300
This Southwest deal was found by Cheapflights users on 9/18. 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.
Mon 10/194:20 pm -
1 stop3h 35m
Thu 10/229:20 pm -
Nonstop2h 45m
Deal found 9/18![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:15 am -
1 stop6h 44m
Thu 11/266:23 am -
1 stop7h 35m
Deal found 9/17![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 9/19. 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 11/216:30 pm -
Nonstop2h 25m
Fri 11/275:55 am -
Nonstop2h 50m
Deal found 9/19![Southwest logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 11/1210:37 pm -
1 stop10h 56m
Sun 11/158:37 pm -
2 stops22h 26m
Deal found 9/20![Multiple Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 9/18. 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 11/261:35 pm -
Nonstop2h 15m
Tue 12/18:55 pm -
Nonstop2h 45m
Deal found 9/18![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:36 am -
1 stop6h 28m
Sun 11/159:30 am -
1 stop6h 44m
Deal found 9/21![Delta logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:44 pm -
1 stop11h 43m
Sun 10/189:33 pm -
1 stop27h 10m
Deal found 9/19![Multiple Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sun 10/186:25 am -
Nonstop2h 20m
Thu 10/229:20 pm -
Nonstop2h 45m
Deal found 9/17![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:25 pm -
1 stop7h 02m
Sun 11/88:29 am -
1 stop7h 38m
Deal found 9/21![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 9/18. 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.
Wed 10/147:00 am -
Nonstop2h 20m
Sat 10/172:20 pm -
1 stop5h 20m
Deal found 9/18![Southwest logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 10/2210:44 pm -
1 stop11h 43m
Sun 10/258:53 pm -
2 stops21h 56m
Deal found 9/20![Multiple Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:20 am -
1 stop5h 39m
Mon 11/98:34 pm -
1 stop14h 24m
Deal found 9/21![Delta logo]()
$343
This Southwest deal was found by Cheapflights users on 9/21. 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 11/145:30 pm -
Nonstop2h 25m
Sun 11/156:30 am -
1 stop4h 20m
Deal found 9/21![Southwest logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/2010:44 pm -
1 stop13h 33m
Sun 10/2510:20 am -
2 stops22h 46m
Deal found 9/17![Multiple Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:20 am -
1 stop5h 39m
Sun 11/88:29 am -
1 stop7h 38m
Deal found 9/21![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 9/21. 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 11/124:10 pm -
1 stop4h 50m
Sun 11/155:20 am -
1 stop5h 35m
Deal found 9/21![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 9/21. 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 10/1711:35 am -
1 stop5h 30m
Sun 10/186:00 am -
Nonstop2h 40m
Deal found 9/21![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 9/18. 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.
Wed 10/286:20 am -
1 stop5h 39m
Wed 10/285:30 pm -
1 stop7h 14m
Deal found 9/18![Delta logo]()
$431
This Southwest deal was found by Cheapflights users on 9/18. 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.
Sun 10/186:25 am -
Nonstop2h 20m
Sun 10/255:25 am -
1 stop5h 45m
Deal found 9/18![Southwest logo]()
$335
Last-minute flights from Denver to ChicagoDiscover last-minute flight deals from Denver to Chicago. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Denver to Chicago. Data last updated September 22, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:40 am -
1 stop8h 49m
Thu 10/228:01 pm -
1 stop23h 00m
Deal found 9/17![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Sat 10/108:55 pm -
Nonstop2h 29m
Tue 10/138:30 am -
1 stop14h 19m
Deal found 9/17![Frontier logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 10/138:55 pm -
Nonstop2h 29m
Sat 10/176:30 am -
Nonstop2h 49m
Deal found 9/19![Frontier logo]()
$179
This Orbitz deal was found by Cheapflights users on 9/18. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:55 pm -
Nonstop2h 29m
Mon 10/197:44 pm -
1 stop13h 22m
Deal found 9/18![Frontier logo]()
$175
This Super.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:55 pm -
Nonstop2h 29m
Sun 10/186:30 am -
Nonstop2h 49m
Deal found 9/18![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 9/17. 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 10/176:10 am -
1 stop7h 15m
Mon 10/197:44 pm -
1 stop13h 22m
Deal found 9/17![Frontier logo]()
$173
This Mytrip deal was found by Cheapflights users on 9/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:12 pm -
2 stops20h 19m
Tue 11/36:30 am -
Nonstop2h 56m
Deal found 9/18![Frontier logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 10/218:55 pm -
Nonstop2h 29m
Tue 10/278:13 pm -
1 stop13h 09m
Deal found 9/19![Frontier logo]()
$177
This Super.com deal was found by Cheapflights users on 9/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:55 pm -
Nonstop2h 29m
Sat 10/246:30 am -
Nonstop2h 49m
Deal found 9/19![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/238:55 pm -
Nonstop2h 29m
Wed 11/46:30 am -
Nonstop2h 56m
Deal found 9/21![Frontier logo]()
$182
This Expedia deal was found by Cheapflights users on 9/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:55 pm -
Nonstop2h 29m
Tue 10/277:50 pm -
1 stop13h 32m
Deal found 9/21![Frontier logo]()
$178
This Southwest deal was found by Cheapflights users on 9/17. 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.
Tue 10/277:00 am -
Nonstop2h 20m
Tue 11/38:55 pm -
Nonstop2h 40m
Deal found 9/17![Southwest logo]()
$189
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 September 22, 2026.
Search for one-way flight options from Denver to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Frontier deal was found by Cheapflights users on 9/20. 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 12/19:26 pm -
Nonstop2h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 9/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/121:10 pm -
1 stop16h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$105
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sat 10/176:55 am -
1 stop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:10 am -
1 stop12h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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.
Mon 11/2311:59 pm -
1 stop18h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:25 am -
1 stop22h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$107
This CheapOair deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:00 am -
1 stop10h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:01 pm -
1 stop11h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1710:40 am -
2 stops12h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$108
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:16 pm -
2 stops17h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$109
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sat 12/56:00 am -
2 stops7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:55 pm -
Nonstop2h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $171 (Cheapflightsfares) |
One-way from | $104 (Frontier) |
Popular in | July |
Cheapest in | January |
Average price | $280 |
Good round-trip deal | $291 or less |
Good one-way deal | $178 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 7,457,451 searches. Data last updated September 22, 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 Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Sat 12/5
6:00 am-2:30 pm
2 stops7h 30m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$110
Quickest round-trip
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Tue 10/13
5:40 pm-9:00 pm
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Wed 10/21
7:00 am-10:20 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Tue 10/20
11:40 am-4:20 pm
1 stop3h 40m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$127
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Thu 12/17
1:26 pm-7:45 pm
1 stop5h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Tue 10/20
6:05 am-2:36 pm
1 stop7h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Sat 10/17
6:20 am-12:59 pm
1 stop5h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Wed 10/21
6:20 am-12:47 pm
1 stop5h 27m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Fri 10/16
12:30 am-7:30 am
1 stop6h 00m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Mon 11/23
6:30 am-11:50 am
1 stop4h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
Showing 1-10 of 59 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 September.
| 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*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| 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, January is the cheapest month in which you can book a flight from Denver to Chicago (average of $231). Flying from Denver to Chicago in July is currently the most expensive (average of $343). 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 September 22, 2026.
It’s optimal to fly from Denver to Chicago in the evening. By choosing this option you can save up to 45% 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 September 22, 2026.
The most flights from DEN to CHI are scheduled on a Sunday (91 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (51 on average).
How much does it cost to fly round-trip from Denver to Chicago?
Airfare is below average for this route at the moment.
Denver to Chicago flights typically cost between $200 and $352 in October.The cheapest round-trip price found within the last 5 days was $171 on Frontier (Oct 6-Oct 22).
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 September 19, 2026.
Travelers seeking maximum savings on their Denver to Chicago flight should consider departing on Saturday evenings 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 September 22, 2026.
See what other customers who have flown with Southwest,United Airlines, andJetBlue 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.
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
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
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.
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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 September 22, 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 September 22, 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 September 22, 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 7,457,451 searches. Data last updated September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$281 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$170 | Average$329 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$175 | Average$298 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$186 | Average$372 | FlexibilityNo cancel fee | On-time69% |