$104+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Nov 29 — Dec 61
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 October 30, 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 October 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/21:15 pm -
1 stop9h 20m
Tue 12/88:30 am -
1 stop26h 50m
Deal found 10/29![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Wed 12/21:15 pm -
1 stop19h 02m
Sun 12/610:37 pm -
1 stop12h 43m
Deal found 10/28![Frontier logo]()
$221
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:34 pm -
1 stop10h 13m
Mon 11/238:42 pm -
1 stop22h 42m
Deal found 10/27![Frontier logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:34 pm -
1 stop10h 39m
Mon 11/235:12 pm -
1 stop26h 12m
Deal found 10/27![Frontier logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:35 pm -
1 stop22h 58m
Mon 1/45:58 am -
1 stop10h 40m
Deal found 10/28![Frontier logo]()
$245
This Kissandfly.com deal was found by Cheapflights users on 10/28. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:30 pm -
1 stop7h 43m
Mon 11/231:35 pm -
Nonstop2h 19m
Deal found 10/28![Frontier logo]()
$247
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/199:38 pm -
1 stop22h 52m
Wed 12/238:35 pm -
1 stop20h 05m
Deal found 10/29![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 12/49:16 am -
1 stop7h 51m
Sat 12/510:40 am -
1 stop8h 05m
Deal found 10/29![Frontier logo]()
$247
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:35 pm -
1 stop22h 58m
Fri 12/255:58 am -
1 stop10h 59m
Deal found 10/28![Frontier logo]()
$247
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:36 pm -
1 stop12h 30m
Mon 12/710:37 pm -
1 stop9h 07m
Deal found 10/28![Frontier logo]()
$248
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:16 am -
1 stop7h 51m
Sun 12/68:37 pm -
1 stop23h 21m
Deal found 10/29![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Fri 12/111:15 pm -
1 stop26h 15m
Sun 12/1310:37 pm -
1 stop12h 43m
Deal found 10/27![Frontier logo]()
$248
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 October 30, 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 October 30, 2026.
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/23:21 pm -
Nonstop2h 58m
Sat 12/56:00 am -
Nonstop2h 20m
Deal found 10/29![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 10/28. 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.
Thu 11/196:35 pm -
Nonstop2h 40m
Wed 12/25:00 am -
Nonstop2h 05m
Deal found 10/28![Southwest logo]()
$259
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/125:40 pm -
Nonstop2h 14m
Mon 12/146:55 am -
Nonstop1h 49m
Deal found 10/28![United Airlines logo]()
$275
This KAYAK deal was found by Cheapflights users on 10/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:30 pm -
Nonstop3h 07m
Fri 11/206:59 am -
1 stop5h 20m
Deal found 10/28![American Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 10/29. 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 12/33:21 pm -
Nonstop2h 58m
Sat 12/56:00 am -
Nonstop2h 20m
Deal found 10/29![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 10/27. 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 11/198:45 am -
1 stop7h 45m
Mon 11/235:00 am -
Nonstop2h 05m
Deal found 10/27![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/73:21 pm -
Nonstop2h 58m
Sat 12/121:35 pm -
Nonstop2h 30m
Deal found 10/27![Delta logo]()
$259
This United Airlines deal was found by Cheapflights users on 10/25. 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.
Sat 12/197:25 pm -
1 stop5h 36m
Wed 12/236:10 pm -
Nonstop2h 16m
Deal found 10/25![United Airlines logo]()
$290
This Southwest deal was found by Cheapflights users on 10/29. 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 12/1210:05 am -
1 stop7h 25m
Mon 12/148:10 am -
2 stops8h 05m
Deal found 10/29![Southwest logo]()
$282
This United deal was found by Cheapflights users on 10/29. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:24 pm -
2 stops21h 15m
Wed 12/96:20 pm -
2 stops21h 39m
Deal found 10/29![Multiple Airlines logo]()
$658
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 12/306:15 am -
Nonstop2h 28m
Tue 1/56:15 pm -
Nonstop1h 59m
Deal found 10/28![United Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 11/206:05 am -
Nonstop2h 37m
Mon 11/238:45 am -
Nonstop2h 14m
Deal found 10/29![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 10/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:40 am -
Nonstop2h 25m
Mon 12/75:00 am -
Nonstop2h 05m
Deal found 10/25![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Wed 1/131:06 pm -
Nonstop2h 34m
Mon 2/16:25 am -
Nonstop2h 02m
Deal found 10/27![United Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 12/48:30 pm -
Nonstop2h 43m
Sat 12/126:10 pm -
Nonstop2h 21m
Deal found 10/29![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 10/30. 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.
Sat 12/510:20 am -
Nonstop2h 50m
Wed 12/97:05 pm -
Nonstop2h 05m
Deal found 10/30![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/35:45 am -
1 stop4h 52m
Sun 12/66:50 am -
Nonstop1h 51m
Deal found 10/28![United Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 10/28. 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 12/47:05 pm -
Nonstop2h 40m
Thu 12/106:00 am -
Nonstop2h 18m
Deal found 10/28![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/265:45 am -
2 stops8h 15m
Thu 12/312:50 pm -
1 stop4h 20m
Deal found 10/26![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 10/28. 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.
Sun 12/136:59 pm -
1 stop5h 57m
Mon 12/147:05 am -
1 stop4h 00m
Deal found 10/28![Delta logo]()
$280
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 12/175:40 pm -
1 stop6h 30m
Sun 12/207:00 pm -
Nonstop1h 55m
Deal found 10/26![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Tue 12/226:30 am -
Nonstop2h 22m
Fri 12/255:55 pm -
Nonstop1h 52m
Deal found 10/27![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 12/185:50 am -
1 stop4h 47m
Mon 12/216:15 pm -
1 stop4h 13m
Deal found 10/29![Delta logo]()
$283
This KAYAK deal was found by Cheapflights users on 10/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/94:36 pm -
Nonstop2h 54m
Sun 11/157:30 pm -
Nonstop2h 19m
Deal found 10/27![American Airlines logo]()
$543
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/205:24 pm -
Nonstop2h 41m
Mon 1/257:30 am -
Nonstop2h 06m
Deal found 10/26![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 10/26. 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.
Fri 12/1112:00 pm -
Nonstop2h 50m
Sun 12/132:20 pm -
Nonstop2h 00m
Deal found 10/26![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 11/182:05 pm -
1 stop5h 17m
Fri 11/205:05 pm -
1 stop5h 23m
Deal found 10/28![Delta logo]()
$288
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:30 am -
Nonstop2h 03m
Sun 11/2210:30 am -
Nonstop1h 47m
Deal found 10/29![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 10/30. 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 11/208:55 pm -
Nonstop2h 35m
Mon 11/232:40 pm -
1 stop5h 15m
Deal found 10/30![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 10/26. 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.
Wed 12/166:00 am -
1 stop5h 59m
Fri 12/1810:05 am -
1 stop6h 25m
Deal found 10/26![Delta logo]()
$294
Last-minute flights from New York to ChicagoDiscover last-minute flight deals from New York to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from New York to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:34 pm -
1 stop10h 13m
Mon 11/238:42 pm -
1 stop22h 42m
Deal found 10/27![Frontier logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:34 pm -
1 stop10h 39m
Mon 11/235:12 pm -
1 stop26h 12m
Deal found 10/27![Frontier logo]()
$234
This Kissandfly.com deal was found by Cheapflights users on 10/28. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:30 pm -
1 stop7h 43m
Mon 11/231:35 pm -
Nonstop2h 19m
Deal found 10/28![Frontier logo]()
$247
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:30 pm -
1 stop7h 43m
Tue 11/247:49 am -
1 stop11h 11m
Deal found 10/28![Frontier logo]()
$248
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:29 am -
1 stop9h 18m
Tue 11/249:09 am -
1 stop9h 51m
Deal found 10/28![Frontier logo]()
$248
This Trip.com deal was found by Cheapflights users on 10/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:29 am -
1 stop9h 18m
Mon 11/239:09 am -
1 stop9h 51m
Deal found 10/28![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:29 am -
1 stop12h 04m
Sat 11/217:49 am -
1 stop11h 11m
Deal found 10/28![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:29 am -
1 stop9h 18m
Sat 11/218:28 am -
1 stop10h 32m
Deal found 10/28![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:29 am -
1 stop10h 16m
Thu 11/267:49 am -
1 stop11h 11m
Deal found 10/28![Frontier logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 11/206:30 am -
1 stop8h 14m
Mon 11/237:49 am -
1 stop11h 11m
Deal found 10/28![Frontier logo]()
$254
This Trip.com deal was found by Cheapflights users on 10/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:14 pm -
1 stop12h 00m
Mon 11/238:42 pm -
1 stop22h 42m
Deal found 10/25![Frontier logo]()
$247
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:20 pm -
1 stop28h 22m
Sat 11/287:49 am -
1 stop11h 47m
Deal found 10/30![Frontier logo]()
$247
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 October 30, 2026.
Search for one-way flight options from New York to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:20 pm -
1 stop23h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:20 pm -
1 stop28h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$104
This Expedia deal was found by Cheapflights users on 10/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/91:15 pm -
1 stop9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$105
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/126:00 am -
Nonstop2h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$109
This Southwest deal was found by Cheapflights users on 10/29. 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.
Wed 12/166:05 pm -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:45 pm -
2 stops43h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Multiple Airlines logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:35 pm -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$116
This Delta deal was found by Cheapflights users on 10/28. 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.
Sat 12/122:32 pm -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Delta logo]()
$119
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:34 pm -
1 stop6h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$120
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:38 pm -
Nonstop2h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$124
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:34 pm -
1 stop10h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 10/27. 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.
Fri 12/112:30 pm -
1 stop11h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$124
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (Kiwi.com) |
One-way from | $104 (Cheapflightsfares) |
Popular in | October |
Cheapest in | January |
Average price | $345 |
Good round-trip deal | $325 or less |
Good one-way deal | $172 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 October 30, 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
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Wed 12/16
6:05 pm-7:30 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Sat 11/21
6:40 pm-8:15 pm
Nonstop2h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Wed 12/2
6:05 pm-7:30 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Thu 12/3
6:05 pm-7:30 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
BuffaloChicago
BUF Buffalo - ORD Chicago O'Hare Intl
BUFORD
Buffalo
Thu 12/17
6:35 pm-12:56 am
1 stop7h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$116
AlbanyChicago
ALB Albany Intl - ORD Chicago O'Hare Intl
ALBORD
Albany Intl
Sat 12/12
2:32 pm-8:53 pm
1 stop7h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$119
AlbanyChicago
ALB Albany Intl - ORD Chicago O'Hare Intl
ALBORD
Albany Intl
Sat 12/12
5:45 am-9:37 am
1 stop4h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$119
AlbanyChicago
ALB Albany Intl - ORD Chicago O'Hare Intl
ALBORD
Albany Intl
Mon 11/23
5:40 am-10:30 am
1 stop5h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$119
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Mon 11/23
5:40 pm-11:10 pm
1 stop6h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$119
RochesterChicago
ROC Greater Rochester Intl - ORD Chicago O'Hare Intl
ROCORD
Greater Rochester Intl
Thu 11/19
1:08 pm-2:29 pm
Nonstop2h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
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.
JFK-ORD
LGA-MDW
BUF-ORD
ALB-ORD
ALB-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
JFK-ORD
LGA-MDW
BUF-ORD
ALB-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 $207). Flying from State of New York to Chicago in October is currently the most expensive (average of $370). 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 October 30, 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 13% versus a flight at noon.
How much does it cost to fly round-trip from State of New York to Chicago?
Airfare is typical for this route at the moment.
State of New York to Chicago flights typically cost between $137 and $307 in November.The cheapest round-trip price found within the last 5 days was $259 on Delta (Nov 19-Dec 2).
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 88 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 October 24, 2026.
Travelers seeking maximum savings on their State of New York to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Monday 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.
Alternative routes
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Complete your 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 October 30, 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 October 30, 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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$39 | Average$171 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$74 | Average$378 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$135 | Average$240 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$376 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$148 | Average$385 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$183 | Average$409 | FlexibilityNo cancel fee | On-time63% |