$87+ Cheap flights from John F Kennedy Intl, NY (JFK) to Chicago (CHI)
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 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Jun 7 — Jun 141
Round-trip
1 adult, Economy
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Find cheap flights from John F Kennedy Intl 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.Cheapflights Tip: The best prices from New York John F Kennedy Intl to Chicago are usually found in January or December, booked 88 days in advance, depart on a Saturday or Wednesday and return on a Friday
Cheap flight deals from John F Kennedy Intl to Chicago
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Cheapest flights from John F Kennedy Intl to ChicagoExplore the most affordable flight options available from John F Kennedy Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 8, 2026.
Explore the most affordable flight options available from John F Kennedy Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 8, 2026.
This Expedia deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/261:00 pm
JFK
- ORD
1 stop7h 41m
Multiple Airlines
Sat 6/136:00 am
ORD
- JFK
Nonstop2h 20m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$159
This flygcity.se deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Fri 6/196:00 am
ORD
- JFK
Nonstop2h 20m
JetBlue
Deal found 5/3![JetBlue logo]()
$161
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/261:00 pm
JFK
- ORD
1 stop7h 41m
Multiple Airlines
Fri 5/2910:45 am
ORD
- JFK
Nonstop2h 32m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$164
This SmartFares deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Sun 6/286:00 am
ORD
- JFK
Nonstop2h 20m
JetBlue
Deal found 5/3![JetBlue logo]()
$168
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/261:00 pm
JFK
- ORD
1 stop7h 41m
Multiple Airlines
Tue 6/23:27 pm
ORD
- JFK
Nonstop2h 32m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 8/181:00 pm
JFK
- MDW
1 stop10h 11m
Frontier
Wed 8/2612:04 pm
MDW
- JFK
1 stop22h 47m
Frontier
Deal found 5/5![Frontier logo]()
$169
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:00 pm
JFK
- ORD
Nonstop2h 55m
JetBlue
Sat 7/256:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 5/5![JetBlue logo]()
$172
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Fri 7/108:00 pm
JFK
- ORD
Nonstop2h 55m
JetBlue
Sat 7/116:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 5/5![JetBlue logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/261:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Fri 5/2912:04 pm
MDW
- JFK
1 stop22h 35m
Frontier
Deal found 5/4![Frontier logo]()
$174
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/77:05 am
JFK
- ORD
Nonstop2h 43m
JetBlue
Wed 7/156:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 5/5![JetBlue logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/41:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Mon 6/812:04 pm
MDW
- JFK
1 stop22h 55m
Frontier
Deal found 5/6![Frontier logo]()
$175
This JetBlue deal was found by Cheapflights users on 5/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:05 am
JFK
- ORD
Nonstop2h 43m
JetBlue
Tue 7/286:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 5/8![JetBlue logo]()
$177
Best flights from John F Kennedy Intl to ChicagoDiscover carefully curated flight deals from John F Kennedy Intl to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 8, 2026.
Discover carefully curated flight deals from John F Kennedy Intl to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 8, 2026.
This JetBlue deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/68:00 am
JFK
- ORD
Nonstop2h 54m
JetBlue
Wed 6/103:39 pm
ORD
- JFK
Nonstop2h 33m
JetBlue
Deal found 5/6![JetBlue logo]()
$197
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 7/38:40 am
JFK
- ORD
1 stop6h 36m
Delta
Sun 7/56:05 am
ORD
- JFK
Nonstop2h 21m
Delta
Deal found 5/3![Delta logo]()
$237
This KAYAK deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/2210:10 am
JFK
- ORD
Nonstop2h 57m
American Airlines
Tue 6/238:00 am
ORD
- JFK
1 stop4h 48m
American Airlines
Deal found 5/4![American Airlines logo]()
$315
This JetBlue deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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.
Tue 6/237:29 pm
JFK
- ORD
Nonstop3h 00m
JetBlue
Tue 6/306:27 pm
ORD
- JFK
Nonstop2h 46m
JetBlue
Deal found 5/7![JetBlue logo]()
$231
This JetBlue deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:00 am
JFK
- ORD
Nonstop2h 54m
JetBlue
Tue 6/93:27 pm
ORD
- JFK
Nonstop2h 32m
JetBlue
Deal found 5/3![JetBlue logo]()
$246
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/103:00 pm
JFK
- ORD
Nonstop3h 11m
Delta
Mon 6/155:30 am
ORD
- JFK
1 stop5h 30m
Delta
Deal found 5/6![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/247:30 am
JFK
- ORD
Nonstop2h 55m
Delta
Sun 6/286:05 am
ORD
- JFK
Nonstop2h 21m
Delta
Deal found 5/5![Delta logo]()
$288
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/213:50 pm
JFK
- ORD
Nonstop3h 04m
Delta
Thu 5/286:34 pm
ORD
- JFK
Nonstop2h 29m
Delta
Deal found 5/7![Delta logo]()
$292
This JetBlue deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:45 pm
JFK
- ORD
Nonstop2h 45m
JetBlue
Wed 5/273:27 pm
ORD
- JFK
Nonstop2h 32m
JetBlue
Deal found 5/3![JetBlue logo]()
$322
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/1012:59 pm
JFK
- ORD
1 stop6h 30m
Delta
Fri 6/125:22 pm
ORD
- JFK
1 stop4h 56m
Delta
Deal found 5/4![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/87:15 am
JFK
- MDW
1 stop6h 54m
Delta
Tue 6/911:05 am
MDW
- JFK
1 stop6h 02m
Delta
Deal found 5/3![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/146:00 am
JFK
- MDW
1 stop5h 09m
Delta
Sat 6/204:25 pm
MDW
- JFK
1 stop5h 39m
Delta
Deal found 5/3![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/287:15 am
JFK
- MDW
1 stop7h 04m
Delta
Fri 5/295:08 pm
MDW
- JFK
1 stop5h 15m
Delta
Deal found 5/5![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/183:45 pm
JFK
- ORD
Nonstop3h 04m
Delta
Sat 5/303:47 pm
ORD
- JFK
1 stop7h 08m
Delta
Deal found 5/7![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/2711:10 am
JFK
- ORD
1 stop8h 32m
Delta
Wed 7/16:05 am
ORD
- JFK
Nonstop2h 21m
Delta
Deal found 5/7![Delta logo]()
$332
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/256:00 am
JFK
- MDW
1 stop5h 09m
Delta
Tue 6/304:25 pm
MDW
- JFK
1 stop5h 39m
Delta
Deal found 5/7![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/3012:59 pm
JFK
- MDW
1 stop6h 26m
Delta
Tue 8/41:27 pm
MDW
- JFK
1 stop5h 42m
Delta
Deal found 5/5![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/256:00 am
JFK
- MDW
1 stop5h 09m
Delta
Wed 7/16:00 am
MDW
- JFK
1 stop5h 00m
Delta
Deal found 5/7![Delta logo]()
$377
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/307:17 am
JFK
- MDW
1 stop6h 29m
Delta
Wed 7/16:00 am
MDW
- JFK
1 stop5h 00m
Delta
Deal found 5/7![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/3112:59 pm
JFK
- MDW
1 stop6h 26m
Delta
Tue 8/45:10 pm
MDW
- JFK
1 stop7h 04m
Delta
Deal found 5/6![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/263:55 pm
JFK
- MDW
1 stop6h 14m
Delta
Fri 5/295:08 pm
MDW
- JFK
1 stop5h 15m
Delta
Deal found 5/5![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 9/136:00 am
JFK
- MDW
1 stop6h 54m
Delta
Tue 9/156:00 am
MDW
- JFK
1 stop6h 27m
Delta
Deal found 5/4![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/2212:00 pm
JFK
- MDW
1 stop6h 56m
Delta
Wed 5/271:22 pm
MDW
- JFK
1 stop4h 07m
Delta
Deal found 5/3![Delta logo]()
$417
Last-minute flights from John F Kennedy Intl to ChicagoDiscover last-minute flight deals from John F Kennedy Intl to Chicago. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from John F Kennedy Intl to Chicago. Data last updated May 8, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/261:00 pm
JFK
- ORD
1 stop7h 41m
Multiple Airlines
Sat 6/136:00 am
ORD
- JFK
Nonstop2h 20m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/261:00 pm
JFK
- ORD
1 stop7h 41m
Multiple Airlines
Fri 5/2910:45 am
ORD
- JFK
Nonstop2h 32m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$164
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/261:00 pm
JFK
- ORD
1 stop7h 41m
Multiple Airlines
Tue 6/23:27 pm
ORD
- JFK
Nonstop2h 32m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/261:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Fri 5/2912:04 pm
MDW
- JFK
1 stop22h 35m
Frontier
Deal found 5/4![Frontier logo]()
$174
This SmartFares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:00 am
JFK
- ORD
Nonstop2h 54m
JetBlue
Fri 6/56:15 am
ORD
- JFK
Nonstop2h 18m
JetBlue
Deal found 5/5![JetBlue logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/41:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Mon 6/812:04 pm
MDW
- JFK
1 stop22h 55m
Frontier
Deal found 5/6![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/137:30 pm
JFK
- ORD
Nonstop3h 00m
JetBlue
Sat 8/85:27 pm
ORD
- JFK
Nonstop2h 33m
JetBlue
Deal found 5/5![JetBlue logo]()
$172
This flygcity.se deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Fri 6/196:00 am
ORD
- JFK
Nonstop2h 20m
JetBlue
Deal found 5/3![JetBlue logo]()
$161
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/207:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Wed 6/246:27 pm
ORD
- JFK
Nonstop2h 46m
JetBlue
Deal found 5/3![JetBlue logo]()
$174
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/207:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Sat 6/205:22 pm
ORD
- JFK
Nonstop2h 38m
JetBlue
Deal found 5/4![JetBlue logo]()
$175
This SmartFares deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Sun 6/286:00 am
ORD
- JFK
Nonstop2h 20m
JetBlue
Deal found 5/3![JetBlue logo]()
$168
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/307:30 am
JFK
- ORD
Nonstop2h 55m
Delta
Sat 7/46:00 pm
ORD
- JFK
Nonstop2h 40m
Delta
Deal found 5/6![Delta logo]()
$177
One-way flights from John F Kennedy Intl to ChicagoSearch for one-way flight options from John F Kennedy Intl to Chicago. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
Search for one-way flight options from John F Kennedy Intl to Chicago. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/137:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Deal found 5/3![JetBlue logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/161:05 pm
JFK
- ORD
1 stop7h 45m
Frontier
Deal found 5/5![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Deal found 5/3![Frontier logo]()
$88
This JetBlue deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/257:25 am
JFK
- ORD
Nonstop2h 43m
JetBlue
Deal found 5/6![JetBlue logo]()
$89
This iWofly deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:00 pm
JFK
- ORD
1 stop7h 41m
Frontier
Deal found 5/4![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/11:00 pm
JFK
- MDW
1 stop23h 12m
Frontier
Deal found 5/7![Frontier logo]()
$90
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Sun 5/248:00 am
JFK
- ORD
Nonstop2h 54m
JetBlue
Deal found 5/4![JetBlue logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/91:05 pm
JFK
- MDW
1 stop10h 06m
Frontier
Deal found 5/6![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/51:00 pm
JFK
- MDW
1 stop23h 04m
Frontier
Deal found 5/5![Frontier logo]()
$94
This Frontier deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/91:05 pm
JFK
- ORD
1 stop7h 48m
Frontier
Deal found 5/5![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/41:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Deal found 5/3![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Mon 6/18:59 pm
JFK
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/4![JetBlue logo]()
$97
Find flight deals from John F Kennedy Intl to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from John F Kennedy Intl (JFK) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $159 (Expedia) |
One-way from | $87 (Super.com) |
Popular in | May |
Cheapest in | January |
Average price | $300 |
Good round-trip deal | $204 or less |
Good one-way deal | $132 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from John F Kennedy Intl 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 2,558,603 searches. Data last updated May 8, 2026.
Use the filters below to find and compare flights from New York John F Kennedy Intl Airport to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sat 6/6
8:00 am-9:54 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 6/10
3:39 pm-7:12 pm
Nonstop2h 33m
$197
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Tue 6/23
7:29 pm-9:29 pm
Nonstop3h 00m
Chicago O'Hare Intl
Tue 6/30
6:27 pm-10:13 pm
Nonstop2h 46m
$231
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Fri 7/3
8:40 am-2:16 pm
1 stop6h 36m
Chicago O'Hare Intl
Sun 7/5
6:05 am-9:26 am
Nonstop2h 21m
$237
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Fri 6/5
8:00 am-9:54 am
Nonstop2h 54m
Chicago O'Hare Intl
Tue 6/9
3:27 pm-6:59 pm
Nonstop2h 32m
$246
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 6/10
3:00 pm-5:11 pm
Nonstop3h 11m
Chicago O'Hare Intl
Mon 6/15
5:30 am-12:00 pm
1 stop5h 30m
$287
Quickest round-trip
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 6/24
7:30 am-9:25 am
Nonstop2h 55m
Chicago O'Hare Intl
Sun 6/28
6:05 am-9:26 am
Nonstop2h 21m
$288
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Thu 5/21
3:50 pm-5:54 pm
Nonstop3h 04m
Chicago O'Hare Intl
Thu 5/28
6:34 pm-10:03 pm
Nonstop2h 29m
$292
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 6/10
12:59 pm-6:29 pm
1 stop6h 30m
Chicago O'Hare Intl
Fri 6/12
5:22 pm-11:18 pm
1 stop4h 56m
$297
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Mon 6/8
7:15 am-1:09 pm
1 stop6h 54m
Chicago Midway
Tue 6/9
11:05 am-6:07 pm
1 stop6h 02m
$297
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Mon 6/22
10:10 am-12:07 pm
Nonstop2h 57m
Chicago O'Hare Intl
Tue 6/23
8:00 am-1:48 pm
1 stop4h 48m
$315
Showing 1-10 of 46 resultsSorted by cheapest first
Compare providers for flights from John F Kennedy Intl 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 from John F Kennedy Intl to Chicago in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on New York John F Kennedy Intl Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New York John F Kennedy Intl Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New York John F Kennedy Intl Airport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on New York John F Kennedy Intl Airport-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New York John F Kennedy Intl Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from John F Kennedy Intl to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from John F Kennedy Intl with our price prediction graph.
JFK-CHI
JFK-ORD
JFK-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 John F Kennedy Intl Airport to Chicago
JFK-CHI
JFK-ORD
JFK-MDW
How far ahead should I book a flight from New York John F Kennedy Intl Airport to Chicago?
Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from New York John F Kennedy Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from New York John F Kennedy Intl Airport to Chicago?
Currently, February is the cheapest month in which you can book a flight from New York John F Kennedy Intl Airport to Chicago (average of $28). Flying from New York John F Kennedy Intl Airport to Chicago in October is currently the most expensive (average of $464). 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 JFK to CHI?
Find hourly flight availability from John F Kennedy Intl 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 May 8, 2026.
One of the essential ways to save on airfare from New York John F Kennedy Intl Airport to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 33% on airfare.
What is the cheapest day to fly from New York John F Kennedy Intl Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from John F Kennedy Intl to Chicago. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their New York John F Kennedy Intl Airport to Chicago flight should consider departing on Monday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from New York John F Kennedy Intl Airport to Chicago
Explore weekly flight availability from John F Kennedy Intl 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 May 8, 2026.
The most flights from JFK to CHI are scheduled on a Friday (44 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (30 on average).
How much does it cost to fly round-trip from New York John F Kennedy Intl Airport to Chicago?
How often are flights from New York to Chicago delayed?
About 24% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 153 minutes.
What is the most punctual flight time for New York to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on New York to Chicago flights?
Over the last year, Delta have had the lowest number of delays on this route, with just 14% of flights being delayed.
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 May 8, 2026.
Read reviews from past customers who have flown Delta,JetBlue, andAmerican Airlines from New York John F Kennedy Intl Airport to Chicago. 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.
Food
7.2
Overall
7.9
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Related info for your journey
Find useful and relevant information for your journey from John F Kennedy Intl to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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John F Kennedy Intl and Chicago flights
Browse other John F Kennedy Intl and Chicago flight options. Last updated on May 8, 2026.
Other flights from John F Kennedy Intl
Browse through other flights departing from John F Kennedy Intl. Flights are based on user searches made on Cheapflights and were last updated on May 8, 2026.
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Top 4 airlines flying from John F Kennedy Intl to Chicago
Discover the top 4 airlines that operate flights from John F Kennedy Intl 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 2,558,603 searches. Data last updated May 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$47 | Average$120 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$74 | Average$308 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$88 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$281 | FlexibilityNo cancel fee | On-time71% |