$105+ Cheap flights to Chicago
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Sep 30 — Oct 71
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 August 31, 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 August 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/1510:18 am -
1 stop30h 12m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 8/26![Multiple Airlines logo]()
$219
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Wed 9/236:15 am -
1 stop13h 08m
Sat 9/266:20 am -
1 stop8h 40m
Deal found 8/27![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/236:15 am -
1 stop12h 36m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 8/27![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/236:15 am -
1 stop6h 36m
Wed 9/306:20 am -
1 stop8h 40m
Deal found 8/26![Frontier logo]()
$223
This CheapOair deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Sat 10/1010:29 pm -
1 stop11h 52m
Mon 10/128:11 pm -
1 stop27h 51m
Deal found 8/25![Frontier logo]()
$224
This Frontier deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/3010:29 pm -
1 stop11h 51m
Sat 10/33:50 pm -
1 stop8h 11m
Deal found 8/27![Frontier logo]()
$225
This Priceline deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:30 pm -
1 stop12h 15m
Tue 9/293:50 pm -
1 stop8h 11m
Deal found 8/25![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/210:29 pm -
1 stop10h 24m
Fri 9/253:50 pm -
1 stop8h 11m
Deal found 8/26![Frontier logo]()
$227
This Orbitz deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/15:55 am -
1 stop18h 04m
Sat 10/33:50 pm -
1 stop8h 11m
Deal found 8/27![Frontier logo]()
$228
This Super.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/156:15 am -
1 stop6h 36m
Thu 9/176:00 am -
1 stop12h 44m
Deal found 8/26![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/110:28 am -
1 stop29h 17m
Wed 10/77:11 am -
1 stop25h 17m
Deal found 8/28![Multiple Airlines logo]()
$228
This FlightHub deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:35 am -
1 stop7h 48m
Fri 9/183:50 pm -
1 stop8h 11m
Deal found 8/30![Frontier logo]()
$229
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 August 31, 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 August 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/110:28 am -
1 stop29h 17m
Wed 10/77:11 am -
1 stop25h 17m
Deal found 8/28![Multiple Airlines logo]()
$228
This JetBlue deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Sat 10/108:15 pm -
Nonstop2h 55m
Sat 10/176:10 am -
Nonstop2h 20m
Deal found 8/25![JetBlue logo]()
$267
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 12/259:52 pm -
Nonstop2h 47m
Sat 1/27:55 pm -
Nonstop2h 19m
Deal found 8/25![United Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am -
Nonstop2h 29m
Sun 9/207:00 am -
Nonstop2h 15m
Deal found 8/26![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/18:55 am -
Nonstop2h 30m
Sun 10/45:05 am -
Nonstop2h 05m
Deal found 8/27![Southwest logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/156:45 pm -
1 stop25h 21m
Mon 10/1910:39 am -
1 stop6h 32m
Deal found 8/26![Allegiant Air logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/110:28 am -
2 stops15h 17m
Sat 10/37:11 am -
1 stop26h 47m
Deal found 8/26![Multiple Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:45 pm -
Nonstop2h 33m
Sat 9/265:30 pm -
Nonstop2h 18m
Deal found 8/25![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:25 pm -
1 stop6h 10m
Sun 9/275:25 am -
Nonstop2h 00m
Deal found 8/30![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 11/124:30 pm -
Nonstop2h 52m
Sun 11/158:45 am -
Nonstop2h 14m
Deal found 8/29![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:35 pm -
1 stop5h 05m
Sun 11/88:15 am -
Nonstop2h 10m
Deal found 8/28![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/107:20 am -
Nonstop2h 40m
Mon 9/143:00 pm -
Nonstop2h 25m
Deal found 8/28![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/255:30 pm -
Nonstop2h 45m
Sun 9/277:00 am -
Nonstop2h 15m
Deal found 8/28![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:20 pm -
1 stop6h 40m
Sun 10/185:05 am -
Nonstop2h 05m
Deal found 8/27![Southwest logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/1811:53 am -
1 stop28h 37m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 8/28![Multiple Airlines logo]()
$312
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 12/288:15 am -
Nonstop2h 48m
Fri 1/16:10 pm -
1 stop4h 34m
Deal found 8/30![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/234:30 pm -
Nonstop2h 50m
Sun 10/256:15 am -
Nonstop2h 12m
Deal found 8/25![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/295:40 pm -
Nonstop2h 30m
Tue 10/68:05 am -
1 stop5h 20m
Deal found 8/30![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 12/217:15 am -
Nonstop2h 48m
Thu 12/313:00 pm -
Nonstop2h 15m
Deal found 8/30![United Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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
Mon 10/52:25 pm -
1 stop6h 00m
Deal found 8/26![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:35 am -
Nonstop2h 52m
Tue 10/610:30 am -
Nonstop2h 24m
Deal found 8/29![Delta logo]()
$286
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/126:00 am -
1 stop4h 38m
Sat 9/126:22 pm -
1 stop4h 08m
Deal found 8/27![United Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 12/1011:06 am -
1 stop8h 56m
Sun 12/136:10 pm -
1 stop13h 42m
Deal found 8/27![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:46 pm -
1 stop16h 06m
Thu 1/75:26 pm -
1 stop14h 25m
Deal found 8/28![Allegiant Air logo]()
$449
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/246:00 am -
2 stops10h 15m
Mon 10/265:10 pm -
Nonstop2h 05m
Deal found 8/29![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:50 pm -
Nonstop2h 41m
Sun 9/207:00 am -
Nonstop2h 15m
Deal found 8/28![Delta logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/2912:17 pm -
2 stops20h 37m
Mon 11/210:44 am -
1 stop12h 19m
Deal found 8/26![Multiple Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 11/77:25 am -
Nonstop2h 35m
Sat 11/710:25 am -
2 stops10h 45m
Deal found 8/29![Southwest logo]()
$282
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 12/3111:22 am -
Nonstop2h 46m
Sun 1/39:47 pm -
Nonstop2h 12m
Deal found 8/25![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am -
1 stop4h 07m
Sat 9/199:29 am -
1 stop5h 30m
Deal found 8/25![Delta logo]()
$287
Last-minute flights to ChicagoDiscover last-minute flight deals to Chicago. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals to Chicago. Data last updated August 31, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/210:29 pm -
1 stop10h 24m
Fri 9/253:50 pm -
1 stop8h 11m
Deal found 8/26![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:29 pm -
1 stop10h 24m
Thu 9/243:50 pm -
1 stop8h 11m
Deal found 8/26![Frontier logo]()
$232
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/1210:29 pm -
1 stop11h 51m
Tue 9/153:50 pm -
1 stop8h 11m
Deal found 8/27![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:30 pm -
1 stop7h 59m
Wed 9/163:50 pm -
1 stop8h 11m
Deal found 8/25![Frontier logo]()
$228
This Super.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/156:15 am -
1 stop6h 36m
Thu 9/176:00 am -
1 stop12h 44m
Deal found 8/26![Frontier logo]()
$228
This FlightHub deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:35 am -
1 stop7h 48m
Fri 9/183:50 pm -
1 stop8h 11m
Deal found 8/30![Frontier logo]()
$229
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Wed 9/236:15 am -
1 stop13h 08m
Sat 9/266:20 am -
1 stop8h 40m
Deal found 8/27![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/236:15 am -
1 stop12h 36m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 8/27![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/236:15 am -
1 stop6h 36m
Wed 9/306:20 am -
1 stop8h 40m
Deal found 8/26![Frontier logo]()
$223
This Priceline deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:30 pm -
1 stop12h 15m
Tue 9/293:50 pm -
1 stop8h 11m
Deal found 8/25![Frontier logo]()
$226
This MakeMyTrip deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure MakeMyTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:15 am -
1 stop6h 36m
Sat 10/36:20 am -
1 stop8h 40m
Deal found 8/27![Frontier logo]()
$232
This Frontier deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/3010:29 pm -
1 stop11h 51m
Sat 10/33:50 pm -
1 stop8h 11m
Deal found 8/27![Frontier logo]()
$225
One-way flights to ChicagoSearch for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/2910:38 am -
1 stop29h 59m
Deal found 8/29![Multiple Airlines logo]()
$105
This Super.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/105:55 am -
1 stop26h 36m
Deal found 8/26![Frontier logo]()
$108
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/151:00 pm -
1 stop6h 23m
Deal found 8/27![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/151:00 pm -
1 stop5h 46m
Deal found 8/27![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/175:55 am -
1 stop18h 04m
Deal found 8/25![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/156:15 am -
1 stop6h 36m
Deal found 8/27![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/221:00 pm -
1 stop6h 23m
Deal found 8/27![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/1511:35 am -
1 stop7h 11m
Deal found 8/30![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/221:30 pm -
1 stop7h 59m
Deal found 8/27![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/226:15 am -
1 stop6h 36m
Deal found 8/27![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/191:00 pm -
1 stop6h 23m
Deal found 8/27![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/2311:35 am -
1 stop7h 16m
Deal found 8/27![Frontier logo]()
$111
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 August 31, 2026.
Popular in | July |
|---|---|
Cheapest in | January |
Average price | $299 |
Round-trip from | $219 |
One-way from | $105 |
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 August 31, 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 WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 10/1
10:28 am-2:45 pm
1 stop29h 17m
Chicago O'Hare Intl
Wed 10/7
7:11 am-9:28 am
1 stop25h 17m
$228
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 10/1
10:28 am-12:45 am
2 stops15h 17m
Chicago O'Hare Intl
Sat 10/3
7:11 am-10:58 am
1 stop26h 47m
$229
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Sat 10/10
8:15 pm-10:10 pm
Nonstop2h 55m
Chicago O'Hare Intl
Sat 10/17
6:10 am-9:30 am
Nonstop2h 20m
$267
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Fri 12/25
9:52 pm-11:39 pm
Nonstop2h 47m
Chicago O'Hare Intl
Sat 1/2
7:55 pm-11:14 pm
Nonstop2h 19m
$267
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Thu 9/17
6:00 am-7:29 am
Nonstop2h 29m
Chicago O'Hare Intl
Sun 9/20
7:00 am-10:15 am
Nonstop2h 15m
$267
Quickest round-trip
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Thu 10/1
8:55 am-10:25 am
Nonstop2h 30m
Chicago Midway
Sun 10/4
5:05 am-8:10 am
Nonstop2h 05m
$267
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Tue 9/22
8:45 pm-10:18 pm
Nonstop2h 33m
Chicago O'Hare Intl
Sat 9/26
5:30 pm-8:48 pm
Nonstop2h 18m
$267
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Thu 11/12
4:30 pm-6:22 pm
Nonstop2h 52m
Chicago O'Hare Intl
Sun 11/15
8:45 am-11:59 am
Nonstop2h 14m
$267
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Fri 9/25
5:30 pm-7:15 pm
Nonstop2h 45m
Chicago O'Hare Intl
Sun 9/27
7:00 am-10:15 am
Nonstop2h 15m
$267
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Fri 10/23
4:30 pm-6:20 pm
Nonstop2h 50m
Chicago O'Hare Intl
Sun 10/25
6:15 am-9:27 am
Nonstop2h 12m
$267
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 August.
| 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
SWF-ORD
JFK-ORD
EWR-ORD
LGA-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
JFK-ORD
EWR-ORD
LGA-ORD
How long is the flight to Chicago?
On average, a flight from New York to Chicago takes 7 hours 26 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 (179 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (138 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 37 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 August 22, 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 August 31, 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
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Comfort
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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