$108+ Cheap flights to Chicago
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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Nov 16 — Nov 231
Round-trip
1 adult, Economy
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1. Tell us where you want to go
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Cheapest flights to ChicagoExplore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on October 17, 2026.
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on October 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Sun 11/226:48 pm -
1 stop29h 46m
Thu 12/36:10 am -
1 stop10h 49m
Deal found 10/12![Multiple Airlines logo]()
$238
This Travelocity deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:30 am -
1 stop13h 00m
Wed 11/188:59 am -
1 stop11h 00m
Deal found 10/12![Frontier logo]()
$246
This deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/296:56 am -
1 stop6h 45m
Thu 12/39:30 am -
1 stop6h 00m
Deal found 10/12![American Airlines logo]()
$247
This Cheapflightsfares deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 10/269:29 am -
1 stop10h 02m
Mon 11/27:50 pm -
1 stop11h 44m
Deal found 10/12![Frontier logo]()
$249
This Cheapflightsfares deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/79:29 am -
1 stop9h 18m
Thu 11/1212:20 pm -
1 stop7h 39m
Deal found 10/12![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/105:30 pm -
1 stop7h 17m
Mon 11/166:08 am -
1 stop12h 27m
Deal found 10/12![Frontier logo]()
$250
This Trip.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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.
Wed 10/214:59 pm -
1 stop7h 44m
Wed 11/116:08 am -
1 stop8h 53m
Deal found 10/13![Frontier logo]()
$251
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 10/316:30 am -
1 stop7h 21m
Tue 11/38:59 am -
1 stop11h 00m
Deal found 10/12![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 10/316:30 am -
1 stop12h 17m
Thu 11/126:08 am -
1 stop12h 27m
Deal found 10/12![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/59:15 am -
1 stop10h 22m
Wed 12/98:15 am -
1 stop7h 14m
Deal found 10/12![Frontier logo]()
$254
This Trip.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Thu 12/39:16 am -
1 stop6h 39m
Mon 12/79:37 pm -
1 stop24h 38m
Deal found 10/12![Frontier logo]()
$256
This Frontier deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 10/216:10 am -
1 stop6h 22m
Fri 11/610:19 am -
1 stop8h 16m
Deal found 10/13![Frontier logo]()
$257
Best flights to ChicagoDiscover carefully curated flight deals to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 17, 2026.
Discover carefully curated flight deals to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 17, 2026.
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/197:35 pm -
Nonstop3h 07m
Fri 11/276:00 am -
Nonstop2h 24m
Deal found 10/13![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/67:29 pm -
Nonstop2h 51m
Mon 11/98:10 pm -
Nonstop2h 19m
Deal found 10/12![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/1210:20 am -
Nonstop2h 50m
Tue 11/177:05 pm -
Nonstop2h 05m
Deal found 10/13![Southwest logo]()
$297
This JetBlue deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:40 am -
1 stop6h 20m
Wed 11/181:00 pm -
1 stop5h 59m
Deal found 10/12![JetBlue logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 12/1612:39 pm -
2 stops13h 22m
Thu 1/78:25 am -
1 stop9h 46m
Deal found 10/13![Multiple Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/1710:55 am -
Nonstop2h 51m
Thu 11/196:00 am -
Nonstop2h 24m
Deal found 10/14![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 10/16. 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.
Sat 12/57:25 am -
Nonstop2h 35m
Mon 12/79:25 am -
Nonstop2h 05m
Deal found 10/16![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 12/318:30 pm -
Nonstop2h 45m
Sun 1/36:00 am -
Nonstop2h 11m
Deal found 10/13![United Airlines logo]()
$312
This JetBlue deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:00 pm -
1 stop7h 00m
Wed 11/41:00 pm -
1 stop5h 59m
Deal found 10/12![JetBlue logo]()
$321
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/113:21 pm -
Nonstop2h 59m
Wed 11/186:00 pm -
Nonstop2h 29m
Deal found 10/12![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 1/1412:00 pm -
Nonstop2h 30m
Mon 1/181:55 pm -
Nonstop2h 05m
Deal found 10/14![Southwest logo]()
$297
This JetBlue deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:15 pm -
Nonstop2h 55m
Wed 11/181:00 pm -
1 stop5h 59m
Deal found 10/13![JetBlue logo]()
$321
This Delta deal was found by Cheapflights users on 10/16. 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.
Tue 1/510:50 am -
Nonstop2h 46m
Sat 1/91:30 pm -
Nonstop2h 25m
Deal found 10/16![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/2310:20 am -
Nonstop2h 50m
Fri 11/279:35 am -
Nonstop2h 05m
Deal found 10/12![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/189:52 pm -
Nonstop2h 47m
Sun 1/39:47 pm -
Nonstop2h 12m
Deal found 10/15![United Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/1912:39 pm -
2 stops49h 11m
Wed 12/305:00 am -
1 stop29h 17m
Deal found 10/14![Multiple Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 10/15. 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 12/84:34 pm -
Nonstop2h 49m
Tue 12/152:39 pm -
Nonstop2h 21m
Deal found 10/15![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Thu 11/52:34 pm -
Nonstop2h 47m
Sat 11/79:00 pm -
Nonstop2h 10m
Deal found 10/16![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 10/15. 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.
Sat 11/216:30 pm -
1 stop6h 55m
Mon 11/235:00 am -
Nonstop2h 05m
Deal found 10/15![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/1212:39 pm -
2 stops13h 15m
Sun 12/136:10 am -
1 stop10h 49m
Deal found 10/12![Multiple Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 10/15. 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 1/76:30 pm -
Nonstop2h 45m
Mon 1/112:30 pm -
Nonstop2h 15m
Deal found 10/15![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/195:05 pm -
1 stop5h 30m
Sun 11/229:35 am -
Nonstop2h 05m
Deal found 10/12![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Thu 10/293:32 pm -
Nonstop2h 47m
Sun 11/15:55 am -
Nonstop2h 04m
Deal found 10/16![United Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/238:30 pm -
Nonstop2h 48m
Fri 11/277:00 am -
Nonstop2h 17m
Deal found 10/12![Delta logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Sun 10/2511:58 am -
1 stop28h 32m
Wed 10/287:15 am -
2 stops25h 33m
Deal found 10/12![Multiple Airlines logo]()
$400
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/268:30 am -
1 stop6h 50m
Fri 12/45:00 am -
Nonstop2h 05m
Deal found 10/12![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:25 pm -
Nonstop2h 48m
Thu 10/299:48 pm -
Nonstop2h 11m
Deal found 10/12![United Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/66:59 pm -
Nonstop2h 44m
Tue 11/102:37 pm -
Nonstop2h 10m
Deal found 10/14![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 10/16. 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 12/97:00 am -
1 stop6h 55m
Mon 12/148:05 am -
Nonstop2h 10m
Deal found 10/16![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 10/2812:39 pm -
2 stops21h 07m
Sat 10/318:00 am -
1 stop27h 08m
Deal found 10/12![Multiple Airlines logo]()
$427
Last-minute flights to ChicagoDiscover last-minute flight deals to Chicago. Data last updated October 17, 2026 and is based on user searches.
Discover last-minute flight deals to Chicago. Data last updated October 17, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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.
Wed 10/214:59 pm -
1 stop7h 44m
Wed 11/116:08 am -
1 stop8h 53m
Deal found 10/13![Frontier logo]()
$251
This Frontier deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 10/216:10 am -
1 stop6h 22m
Fri 11/610:19 am -
1 stop8h 16m
Deal found 10/13![Frontier logo]()
$257
This Cheapflightsfares deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 10/269:29 am -
1 stop10h 02m
Mon 11/27:50 pm -
1 stop11h 44m
Deal found 10/12![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 10/316:30 am -
1 stop12h 17m
Sat 11/77:15 am -
1 stop11h 20m
Deal found 10/12![Frontier logo]()
$253
This CheapOair deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/56:30 am -
1 stop12h 17m
Sat 11/77:15 am -
1 stop11h 20m
Deal found 10/13![Frontier logo]()
$257
This Cheapflightsfares deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/79:29 am -
1 stop9h 18m
Thu 11/1212:20 pm -
1 stop7h 39m
Deal found 10/12![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/78:30 pm -
1 stop13h 52m
Mon 11/167:50 pm -
1 stop11h 44m
Deal found 10/12![Frontier logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/105:30 pm -
1 stop7h 17m
Mon 11/166:08 am -
1 stop12h 27m
Deal found 10/12![Frontier logo]()
$250
This Travelocity deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:30 am -
1 stop13h 00m
Wed 11/188:59 am -
1 stop11h 00m
Deal found 10/12![Frontier logo]()
$246
This Cheapflightsfares deal was found by Cheapflights users on 10/17. 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.
Thu 11/129:29 am -
1 stop10h 16m
Sat 11/1410:29 am -
1 stop9h 30m
Deal found 10/17![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Sun 11/226:48 pm -
1 stop29h 46m
Thu 12/36:10 am -
1 stop10h 49m
Deal found 10/12![Multiple Airlines logo]()
$238
This deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/296:56 am -
1 stop6h 45m
Thu 12/39:30 am -
1 stop6h 00m
Deal found 10/12![American Airlines logo]()
$247
One-way flights to ChicagoSearch for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated October 17, 2026.
Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated October 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Sun 11/226:48 pm -
1 stop29h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/106:49 pm -
1 stop20h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$125
This iWofly deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2111:00 pm -
1 stop10h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/1311:00 pm -
1 stop14h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Frontier logo]()
$126
This CheapOair deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/210:24 pm -
1 stop9h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Frontier logo]()
$128
This Mytrip deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Mon 11/2311:30 am -
1 stop9h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Frontier logo]()
$129
This CheapOair deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Mon 11/2311:30 am -
1 stop14h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 12/116:05 am -
1 stop9h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$130
This Frontier deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/711:00 pm -
1 stop11h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/206:30 am -
1 stop8h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Frontier logo]()
$130
This Cheapflightsfares deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/711:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Frontier logo]()
$131
This Super.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:30 am -
1 stop8h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Frontier logo]()
$131
Find flight deals to Chicago
Find the latest flights to Chicago in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 7,457,451 searches and data was last updated on October 17, 2026.
Popular in | October |
|---|---|
Cheapest in | January |
Average price | $340 |
Round-trip from | $238 |
One-way from | $108 |
Good round-trip deal | $202 or less |
Good one-way deal | $150 or less |
Cheapflights Fare Finder
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 7,457,451 searches and data was last updated on October 17, 2026.
Use the filters below to find and compare flights to Chicago that are best for you.
Fly from
Route
Depart
Return
Cheapest round-trip
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Mon 12/14
12:35 pm-4:42 pm
1 stop5h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Tue 12/8
3:21 pm-5:19 pm
Nonstop2h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Tue 12/29
4:48 pm-6:36 pm
Nonstop2h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Mon 11/16
8:30 am-10:05 am
Nonstop2h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Sat 12/12
9:30 am-4:47 pm
1 stop8h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Mon 1/11
7:35 pm-9:33 pm
Nonstop2h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Wed 12/2
12:37 pm-2:23 pm
Nonstop2h 46m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Thu 11/5
8:30 am-10:05 am
Nonstop2h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Tue 12/22
9:52 pm-11:39 pm
Nonstop2h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Wed 1/6
2:30 pm-4:12 pm
Nonstop2h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights 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 to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | 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*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: Out of all of the providers offering Chicago flight deals, Cheapflights users have found FlightHub to have the most accurate pricing on Cheapflights vs. their site about >95% of the time, users can find the same price on Chicago flight deals on Cheapflights and FlightHub. This is based on searches made for Chicago flights over the past month.
- Most trusted provider: FlightHub is the most trusted provider by Cheapflights users offering Chicago flight deals. With a user feedback rating of 3 out of 3 stars (3 being the best), FlightHub has received the most positive sentiment from Cheapflights users searching for flights to Chicago. This is based on data collected from Cheapflights searches made over the past month.
Best time to book a flight to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
NYC-CHI
SWF-ORD
LGA-ORD
LGA-MDW
JFK-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 to Chicago
NYC-CHI
SWF-ORD
LGA-ORD
LGA-MDW
JFK-ORD
How long is the flight to Chicago?
On average, a flight from New York to Chicago takes 3 hours 11 minutes. Flights to Chicago from other popular cities in USA will vary in length. Below are a few examples of popular routes and their flight times.
Weekly flight availability to Chicago
The most flights from New York to Chicago are scheduled on a Friday (195 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (101 on average).
What are the most popular airlines that fly to Chicago?
The most popular airlines flying from New York to Chicago are United Airlines, American Airlines and Delta.
What are the cheapest airlines that fly to Chicago?
The cheapest airlines flying from New York to Chicago are Frontier, Delta and JetBlue.
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
When is the best time to book a flight to Chicago?
The price you pay for your flight to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 88 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
When is the cheapest time to fly to Chicago?
Use this chart to determine the cheapest time to fly round-trip from New York to Chicago. Price data was last updated on October 10, 2026.
Users looking for the lowest fares to Chicago should consider flying on Wednesday evenings, when prices are typically cheapest. Budget-minded travelers will want to avoid Thursday at noon, when prices are usually at their highest.
The best insider tips for flights to Chicago
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 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 October 17, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines to the United States. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
FAQs about flying to Chicago
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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