$116+ Cheap flights from New York State to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Oct 13 — Oct 201
Round-trip
1 adult, Economy
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Find cheap flights from New York to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from New York to Chicago
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Cheapest flights from New York to ChicagoExplore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 13, 2026.
Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 13, 2026.
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/306:15 am -
1 stop6h 36m
Wed 10/76:20 am -
1 stop8h 40m
Deal found 9/9![Frontier logo]()
$228
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/306:15 am -
1 stop12h 36m
Wed 10/76:25 am -
1 stop8h 35m
Deal found 9/9![Frontier logo]()
$228
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Tue 9/296:15 am -
1 stop6h 36m
Wed 9/306:20 am -
1 stop8h 40m
Deal found 9/10![Frontier logo]()
$231
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:15 am -
1 stop12h 31m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/9![Frontier logo]()
$232
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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
Sat 10/247:44 pm -
1 stop11h 50m
Deal found 9/10![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/16:15 am -
1 stop12h 31m
Sat 10/36:25 am -
1 stop8h 35m
Deal found 9/10![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:10 am -
1 stop6h 22m
Wed 10/218:30 am -
1 stop10h 14m
Deal found 9/9![Frontier logo]()
$235
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/10![Frontier logo]()
$235
This JetBlue deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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
Sat 10/39:38 am -
1 stop6h 51m
Deal found 9/9![JetBlue logo]()
$237
This Expedia deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:55 am -
1 stop26h 56m
Mon 10/268:11 pm -
1 stop26h 52m
Deal found 9/11![Frontier logo]()
$237
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Tue 10/66:15 am -
1 stop6h 36m
Tue 10/277:15 am -
1 stop7h 46m
Deal found 9/10![Frontier logo]()
$237
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/296:15 am -
1 stop12h 31m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/10![Frontier logo]()
$237
Best flights from New York to ChicagoDiscover carefully curated flight deals from New York to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 13, 2026.
Discover carefully curated flight deals from New York to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 13, 2026.
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/710:05 am -
Nonstop2h 51m
Sun 11/87:00 am -
Nonstop2h 09m
Deal found 9/8![United Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/215:30 pm -
Nonstop2h 50m
Sat 10/247:00 am -
Nonstop2h 20m
Deal found 9/10![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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
Thu 11/57:15 pm -
Nonstop2h 05m
Deal found 9/9![Southwest logo]()
$267
This JetBlue deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/198:15 pm -
Nonstop2h 55m
Wed 10/219:38 am -
1 stop6h 51m
Deal found 9/10![JetBlue logo]()
$277
This KAYAK deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Thu 9/246:48 am -
Nonstop2h 49m
Fri 9/256:01 pm -
Nonstop2h 28m
Deal found 9/10![American Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/276:59 pm -
Nonstop2h 44m
Tue 11/311:30 am -
Nonstop2h 19m
Deal found 9/8![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/1710:20 am -
Nonstop2h 39m
Sat 10/176:29 pm -
Nonstop2h 25m
Deal found 9/10![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/234:20 pm -
1 stop5h 35m
Sun 10/255:05 am -
Nonstop2h 05m
Deal found 9/10![Southwest logo]()
$277
This JetBlue deal was found by Cheapflights users on 9/12. 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 10/281:26 pm -
1 stop7h 03m
Sat 10/311:00 pm -
1 stop5h 59m
Deal found 9/12![JetBlue logo]()
$278
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/15:30 pm -
Nonstop2h 45m
Fri 10/26:00 am -
Nonstop2h 15m
Deal found 9/10![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/288:05 am -
Nonstop2h 20m
Sat 10/319:55 am -
1 stop6h 55m
Deal found 9/8![Southwest logo]()
$277
This JetBlue deal was found by Cheapflights users on 9/13. 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.
Sat 9/2612:59 pm -
1 stop7h 02m
Tue 9/2910:59 am -
Nonstop2h 21m
Deal found 9/13![JetBlue logo]()
$297
This United deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/69:26 am -
2 stops25h 05m
Sun 11/86:15 am -
2 stops9h 31m
Deal found 9/9![Multiple Airlines logo]()
$656
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:35 pm -
Nonstop2h 23m
Wed 10/145:57 pm -
Nonstop2h 00m
Deal found 9/9![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:30 pm -
Nonstop2h 45m
Tue 10/67:00 am -
Nonstop2h 17m
Deal found 9/8![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:00 am -
Nonstop2h 30m
Tue 10/205:00 am -
Nonstop2h 05m
Deal found 9/11![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:07 am -
Nonstop2h 18m
Mon 10/195:57 pm -
Nonstop2h 00m
Deal found 9/11![United Airlines logo]()
$299
This JetBlue deal was found by Cheapflights users on 9/13. 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.
Wed 9/301:00 pm -
1 stop7h 01m
Fri 10/210:59 am -
Nonstop2h 21m
Deal found 9/13![JetBlue logo]()
$311
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/37:35 pm -
Nonstop3h 08m
Thu 11/56:10 am -
Nonstop2h 17m
Deal found 9/11![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 9/13. 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.
Tue 11/246:30 am -
Nonstop2h 25m
Tue 12/14:55 pm -
Nonstop2h 05m
Deal found 9/13![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/194:25 pm -
Nonstop2h 44m
Mon 10/262:00 pm -
Nonstop2h 15m
Deal found 9/8![United Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/247:30 am -
Nonstop2h 57m
Thu 12/36:00 am -
Nonstop2h 20m
Deal found 9/11![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 9/12. 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.
Sat 10/176:15 am -
Nonstop2h 30m
Mon 10/195:10 am -
Nonstop2h 05m
Deal found 9/12![Southwest logo]()
$287
This JetBlue deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 9/231:00 pm -
1 stop7h 01m
Mon 9/287:00 am -
Nonstop2h 27m
Deal found 9/11![JetBlue logo]()
$321
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/110:40 am -
Nonstop2h 45m
Sun 10/46:00 am -
Nonstop2h 21m
Deal found 9/8![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/54:25 pm -
1 stop7h 15m
Mon 11/95:20 am -
1 stop7h 00m
Deal found 9/10![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 9/12. 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 10/166:07 am -
Nonstop2h 18m
Sun 10/187:35 am -
Nonstop2h 08m
Deal found 9/12![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/27:35 pm -
Nonstop3h 02m
Wed 10/71:55 pm -
1 stop7h 04m
Deal found 9/10![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/306:55 am -
1 stop7h 35m
Sun 10/45:05 am -
Nonstop2h 05m
Deal found 9/10![Southwest logo]()
$292
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/96:20 am -
Nonstop2h 08m
Sat 10/176:06 pm -
1 stop4h 38m
Deal found 9/8![United Airlines logo]()
$327
Last-minute flights from New York to ChicagoDiscover last-minute flight deals from New York to Chicago. Data last updated September 13, 2026 and is based on user searches.
Discover last-minute flight deals from New York to Chicago. Data last updated September 13, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:15 am -
1 stop12h 31m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/9![Frontier logo]()
$232
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Tue 9/296:15 am -
1 stop6h 36m
Wed 9/306:20 am -
1 stop8h 40m
Deal found 9/10![Frontier logo]()
$231
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/296:15 am -
1 stop12h 31m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/10![Frontier logo]()
$237
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/306:15 am -
1 stop6h 36m
Wed 10/76:20 am -
1 stop8h 40m
Deal found 9/9![Frontier logo]()
$228
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/306:15 am -
1 stop12h 36m
Wed 10/76:25 am -
1 stop8h 35m
Deal found 9/9![Frontier logo]()
$228
This JetBlue deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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
Sat 10/39:38 am -
1 stop6h 51m
Deal found 9/9![JetBlue logo]()
$237
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/16:15 am -
1 stop12h 31m
Sat 10/36:25 am -
1 stop8h 35m
Deal found 9/10![Frontier logo]()
$234
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Tue 10/66:15 am -
1 stop6h 36m
Tue 10/277:15 am -
1 stop7h 46m
Deal found 9/10![Frontier logo]()
$237
This Expedia deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:55 am -
1 stop26h 56m
Mon 10/268:11 pm -
1 stop26h 52m
Deal found 9/11![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:10 am -
1 stop6h 22m
Wed 10/218:30 am -
1 stop10h 14m
Deal found 9/9![Frontier logo]()
$235
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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
Sat 10/247:44 pm -
1 stop11h 50m
Deal found 9/10![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/10![Frontier logo]()
$235
One-way flights from New York to ChicagoSearch for one-way flight options from New York to Chicago. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
Search for one-way flight options from New York to Chicago. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/31:00 pm -
1 stop6h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$116
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Fri 10/3011:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$116
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/2911:35 am -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$116
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/36:15 am -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$116
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/296:15 am -
1 stop12h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$116
This Trip.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/1811:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$117
This Priceline deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Sat 10/31:00 pm -
1 stop5h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$117
This Trip.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/305:55 am -
1 stop18h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/66:15 am -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$117
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 stop12h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$117
This Trip.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/411:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/1410:29 pm -
1 stop11h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$118
Find flight deals from New York to Chicago
Keep the following information in mind while searching for New York to Chicago flight deals. Data was last updated September 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $228 (Expedia) |
One-way from | $116 (Super.com) |
Popular in | July |
Cheapest in | January |
Average price | $304 |
Good round-trip deal | $273 or less |
Good one-way deal | $153 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from New York to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 13, 2026.
Use the filters below to find and compare flights from New York State to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Sat 10/17
7:55 am-9:40 am
Nonstop2h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Thu 10/29
6:00 am-7:36 am
Nonstop2h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Sun 11/22
6:45 am-8:10 am
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Wed 9/30
7:17 am-9:00 am
Nonstop2h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Sat 11/7
11:55 am-1:39 pm
Nonstop2h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Wed 11/18
5:35 pm-7:15 pm
Nonstop2h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Sun 11/8
7:29 pm-9:20 pm
Nonstop2h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Fri 10/2
8:45 pm-10:18 pm
Nonstop2h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Wed 10/14
5:55 pm-7:25 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Wed 10/21
7:29 pm-9:13 pm
Nonstop2h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from New York to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.
LGA-ORD
LGA-MDW
JFK-ORD
EWR-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 from New York State to Chicago
USNY-CHI
LGA-ORD
LGA-MDW
JFK-ORD
EWR-ORD
What is the cheapest month to book a flight from State of New York to Chicago?
Currently, January is the cheapest month in which you can book a flight from State of New York to Chicago (average of $203). Flying from State of New York to Chicago in July is currently the most expensive (average of $359). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from NY to CHI?
Find hourly flight availability from New York to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 13, 2026.
When flying from State of New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 23% versus a flight at noon.
Weekly flight availability from State of New York to Chicago
Explore weekly flight availability from New York to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 13, 2026.
The most flights from USNY to CHI are scheduled on a Friday (52 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (40 on average).
How much does it cost to fly round-trip from State of New York to Chicago?
Airfare is below average for this route at the moment.
State of New York to Chicago flights typically cost between $240 and $377 in September.The cheapest round-trip price found within the last 5 days was $237 on JetBlue (Sep 30-Oct 3).
How far ahead should I book a flight from State of New York to Chicago?
The best time to book flights from State of New York to Chicago is 37 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from State of New York 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 12, 2026.
Travelers seeking maximum savings on their State of New York to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from New York to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for New York to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 13, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from New York to Chicago by cabin class
Find flights from New York to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
New York and Chicago flights
Browse other New York and Chicago flight options. Last updated on September 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
New York to Chicago flights
Consider these flights traveling from New York to Chicago.
Top 6 airlines flying from New York to Chicago
Discover the top 6 airlines that operate flights from New York to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$44 | Average$175 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$74 | Average$393 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$122 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$368 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$148 | Average$367 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$391 | FlexibilityNo cancel fee | On-time63% |