$115+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Oct 22 — Oct 291
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 September 22, 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 September 22, 2026.
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:30 pm -
1 stop15h 05m
Sat 11/77:20 pm -
1 stop12h 14m
Deal found 9/19![Frontier logo]()
$234
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:30 am -
1 stop12h 17m
Sat 10/317:25 am -
1 stop12h 21m
Deal found 9/19![Frontier logo]()
$234
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:00 pm -
1 stop7h 03m
Fri 10/96:10 am -
Nonstop2h 20m
Deal found 9/17![JetBlue logo]()
$235
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
Nonstop2h 39m
Wed 10/211:00 pm -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$235
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.
Wed 10/146:00 am -
Nonstop2h 30m
Thu 10/157:35 pm -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$235
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:29 am -
1 stop13h 02m
Tue 10/208:30 am -
1 stop10h 14m
Deal found 9/17![Frontier logo]()
$236
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:29 am -
1 stop9h 18m
Tue 11/106:16 am -
1 stop8h 45m
Deal found 9/19![Frontier logo]()
$236
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:15 pm -
Nonstop2h 53m
Tue 10/610:59 am -
Nonstop2h 21m
Deal found 9/17![JetBlue logo]()
$237
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.
Wed 10/146:10 am -
1 stop6h 22m
Tue 10/208:30 am -
1 stop10h 14m
Deal found 9/21![Frontier logo]()
$237
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.
Thu 10/296:30 am -
2 stops17h 13m
Sat 10/317:15 am -
1 stop7h 46m
Deal found 9/17![Frontier logo]()
$238
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:30 pm -
1 stop7h 17m
Sat 11/147:25 am -
1 stop7h 36m
Deal found 9/21![Frontier logo]()
$238
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:00 am -
Nonstop2h 39m
Wed 10/1411:00 am -
Nonstop2h 23m
Deal found 9/17![United Airlines logo]()
$239
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 September 22, 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 September 22, 2026.
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.
Wed 11/47:00 am -
2 stops11h 05m
Fri 11/66:50 am -
1 stop8h 20m
Deal found 9/17![Southwest logo]()
$234
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:23 am -
Nonstop2h 37m
Thu 10/222:00 pm -
Nonstop2h 25m
Deal found 9/17![United Airlines logo]()
$252
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 10/217:30 am -
Nonstop2h 57m
Mon 10/266:10 am -
Nonstop2h 17m
Deal found 9/17![Delta logo]()
$271
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:40 am -
1 stop6h 19m
Fri 11/131:00 pm -
1 stop7h 29m
Deal found 9/19![JetBlue logo]()
$278
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 10/217:20 am -
Nonstop2h 42m
Mon 10/268:20 pm -
Nonstop2h 24m
Deal found 9/17![Delta logo]()
$271
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
1 stop6h 33m
Wed 12/162:00 pm -
Nonstop2h 15m
Deal found 9/17![United Airlines logo]()
$273
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:45 am -
Nonstop2h 25m
Tue 11/108:05 am -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$276
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:30 am -
Nonstop2h 54m
Tue 10/271:00 pm -
1 stop5h 59m
Deal found 9/20![JetBlue logo]()
$283
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.
Sun 10/1111:22 am -
Nonstop2h 46m
Tue 10/138:20 pm -
Nonstop2h 24m
Deal found 9/17![Delta logo]()
$279
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:40 pm -
Nonstop2h 48m
Thu 10/225:00 am -
Nonstop2h 12m
Deal found 9/21![United Airlines logo]()
$287
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:15 am -
Nonstop2h 20m
Mon 10/267:35 pm -
Nonstop2h 10m
Deal found 9/20![Southwest logo]()
$287
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:26 pm -
1 stop6h 51m
Sat 11/141:00 pm -
1 stop5h 59m
Deal found 9/17![JetBlue logo]()
$298
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.
Fri 12/118:30 pm -
Nonstop2h 43m
Sun 12/137:00 am -
Nonstop2h 20m
Deal found 9/17![Delta logo]()
$279
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am -
Nonstop2h 47m
Wed 11/117:00 am -
Nonstop2h 08m
Deal found 9/21![United Airlines logo]()
$287
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 10/158:55 am -
Nonstop2h 30m
Sun 10/185:05 am -
Nonstop2h 05m
Deal found 9/18![Southwest logo]()
$287
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.
Fri 10/307:30 am -
Nonstop2h 57m
Sat 10/315:29 pm -
1 stop4h 38m
Deal found 9/17![Delta logo]()
$281
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:40 pm -
Nonstop2h 48m
Sun 10/185:00 am -
Nonstop2h 13m
Deal found 9/21![United Airlines logo]()
$287
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 11/57:15 am -
1 stop7h 55m
Sun 11/85:00 am -
Nonstop2h 05m
Deal found 9/21![Southwest logo]()
$297
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:35 pm -
Nonstop3h 07m
Tue 11/1710:30 am -
Nonstop2h 16m
Deal found 9/20![Delta logo]()
$287
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:00 am -
Nonstop2h 39m
Wed 10/149:00 am -
Nonstop2h 23m
Deal found 9/19![United Airlines logo]()
$287
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 10/1512:30 pm -
Nonstop2h 20m
Tue 10/209:25 am -
1 stop6h 25m
Deal found 9/18![Southwest logo]()
$297
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.
Mon 11/93:21 pm -
Nonstop2h 59m
Tue 11/101:35 pm -
Nonstop2h 22m
Deal found 9/21![Delta logo]()
$287
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.
Wed 11/46:40 am -
Nonstop2h 25m
Wed 11/43:10 pm -
1 stop6h 45m
Deal found 9/21![Southwest logo]()
$297
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.
Thu 10/224:30 pm -
Nonstop2h 50m
Mon 10/268:36 am -
Nonstop2h 23m
Deal found 9/18![Delta logo]()
$287
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:17 am -
Nonstop2h 43m
Mon 10/57:52 pm -
Nonstop2h 23m
Deal found 9/19![United Airlines logo]()
$325
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 10/36:15 am -
Nonstop2h 30m
Wed 10/77:25 pm -
Nonstop2h 10m
Deal found 9/19![Southwest logo]()
$297
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 11/56:00 am -
Nonstop2h 36m
Thu 11/128:25 pm -
Nonstop2h 17m
Deal found 9/21![Delta logo]()
$287
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.
Sat 11/78:20 am -
2 stops10h 05m
Sun 11/85:00 am -
Nonstop2h 05m
Deal found 9/18![Southwest logo]()
$302
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:05 am -
Nonstop2h 37m
Wed 11/255:50 pm -
Nonstop2h 11m
Deal found 9/20![Delta logo]()
$287
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.
Tue 11/107:00 am -
2 stops11h 05m
Sun 11/155:00 am -
Nonstop2h 05m
Deal found 9/19![Southwest logo]()
$302
Last-minute flights to ChicagoDiscover last-minute flight deals to Chicago. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals to Chicago. Data last updated September 22, 2026 and is based on user searches.
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:00 pm -
1 stop7h 01m
Tue 10/610:59 am -
Nonstop2h 21m
Deal found 9/17![JetBlue logo]()
$240
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:23 am -
Nonstop2h 37m
Tue 10/61:00 pm -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$240
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 10/36:15 am -
Nonstop2h 30m
Tue 10/62:40 pm -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$240
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:00 am -
Nonstop2h 39m
Wed 10/1411:00 am -
Nonstop2h 23m
Deal found 9/17![United Airlines logo]()
$239
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.
Wed 10/146:00 am -
Nonstop2h 30m
Thu 10/157:35 pm -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$235
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.
Wed 10/146:10 am -
1 stop6h 22m
Tue 10/208:30 am -
1 stop10h 14m
Deal found 9/21![Frontier logo]()
$237
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:29 am -
1 stop13h 02m
Tue 10/208:30 am -
1 stop10h 14m
Deal found 9/17![Frontier logo]()
$236
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 10/156:29 am -
1 stop12h 16m
Wed 10/216:21 am -
1 stop8h 53m
Deal found 9/17![Frontier logo]()
$236
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
Nonstop2h 39m
Wed 10/211:00 pm -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$235
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:30 am -
1 stop12h 17m
Sat 10/317:25 am -
1 stop12h 21m
Deal found 9/19![Frontier logo]()
$234
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.
Thu 10/296:30 am -
2 stops17h 13m
Sat 10/317:15 am -
1 stop7h 46m
Deal found 9/17![Frontier logo]()
$238
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:30 pm -
1 stop15h 05m
Sat 11/77:20 pm -
1 stop12h 14m
Deal found 9/19![Frontier logo]()
$234
One-way flights to ChicagoSearch for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:05 am -
1 stop6h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$115
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.
Wed 11/411:35 am -
1 stop7h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$115
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$116
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:35 am -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$116
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$117
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 10/2111:30 am -
1 stop8h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$117
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 11/1111:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$118
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.
Wed 10/711:35 am -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$118
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.
Wed 10/711:35 am -
1 stop7h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$119
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.
Wed 9/3011:35 am -
1 stop7h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$120
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.
Tue 10/611:35 am -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$120
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.
Tue 10/611:35 am -
1 stop7h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$121
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 September 22, 2026.
Popular in | July |
|---|---|
Cheapest in | January |
Average price | $308 |
Round-trip from | $234 |
One-way from | $115 |
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 September 22, 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
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Fri 12/4
6:10 pm-8:06 pm
Nonstop2h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$118
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Sat 10/31
11:22 am-1:09 pm
Nonstop2h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Tue 10/27
10:00 am-11:47 am
Nonstop2h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Wed 10/14
8:00 am-9:45 am
Nonstop2h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Mon 12/14
3:21 pm-5:19 pm
Nonstop2h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$136
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Mon 10/5
8:45 pm-10:18 pm
Nonstop2h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$136
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Sat 10/31
7:37 pm-12:01 am
1 stop5h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Sat 10/24
7:17 am-9:00 am
Nonstop2h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$142
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Wed 10/14
6:00 am-9:38 am
1 stop4h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$142
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Thu 10/29
1:26 pm-7:29 pm
1 stop7h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
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 September.
| 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 Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | 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
LGA-ORD
LGA-MDW
JFK-ORD
EWR-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight to Chicago
NYC-CHI
LGA-ORD
LGA-MDW
JFK-ORD
EWR-MDW
How long is the flight to Chicago?
On average, a flight from New York to Chicago takes 7 hours 31 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 Monday (187 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (64 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 82 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 September 19, 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 September 22, 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.
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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