$132+ Cheap flights from John F Kennedy Intl, NY (JFK) to Midway (MDW)
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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Jul 24 — Jul 311
Round-trip
1 adult, Economy
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Cheapest flights from John F Kennedy Intl to MidwayExplore the most affordable flight options available from John F Kennedy Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 24, 2026.
Explore the most affordable flight options available from John F Kennedy Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 24, 2026.
This Kissandfly.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Sat 8/81:00 pm
JFK
- MDW
1 stop10h 03m
Frontier
Mon 8/106:05 am
MDW
- JFK
1 stop4h 54m
Frontier
Deal found 6/23![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/191:00 pm
JFK
- MDW
1 stop9h 58m
Frontier
Wed 9/2312:03 pm
MDW
- JFK
1 stop22h 48m
Frontier
Deal found 6/23![Frontier logo]()
$293
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/58:35 am
JFK
- MDW
1 stop8h 40m
Delta
Sat 8/84:39 pm
MDW
- JFK
1 stop5h 31m
Delta
Deal found 6/22![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/86:00 am
JFK
- MDW
1 stop5h 05m
Delta
Tue 7/141:18 pm
MDW
- JFK
1 stop4h 11m
Delta
Deal found 6/23![Delta logo]()
$302
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:35 am
JFK
- MDW
1 stop7h 50m
Delta
Sun 9/135:11 pm
MDW
- JFK
1 stop6h 48m
Delta
Deal found 6/23![Delta logo]()
$312
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:20 am
JFK
- MDW
1 stop5h 31m
Delta
Sat 8/156:05 am
MDW
- JFK
1 stop6h 10m
Delta
Deal found 6/19![Delta logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/171:00 pm
JFK
- MDW
1 stop10h 03m
Frontier
Mon 7/206:05 am
MDW
- JFK
1 stop28h 45m
Frontier
Deal found 6/23![Frontier logo]()
$323
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/177:05 am
JFK
- MDW
1 stop5h 46m
Delta
Sat 8/229:24 am
MDW
- JFK
1 stop7h 24m
Delta
Deal found 6/24![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/711:00 am
JFK
- MDW
1 stop6h 15m
Delta
Wed 8/126:05 am
MDW
- JFK
1 stop4h 54m
Delta
Deal found 6/23![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/712:59 pm
JFK
- MDW
1 stop6h 26m
Delta
Wed 7/812:41 pm
MDW
- JFK
1 stop7h 48m
Delta
Deal found 6/23![Delta logo]()
$332
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:28 pm
JFK
- MDW
2 stops16h 11m
Delta
Mon 9/211:00 pm
MDW
- JFK
1 stop8h 03m
Delta
Deal found 6/22![Delta logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/181:00 pm
JFK
- MDW
1 stop10h 03m
Frontier
Mon 7/206:05 am
MDW
- JFK
1 stop28h 45m
Frontier
Deal found 6/23![Frontier logo]()
$339
Best flights from John F Kennedy Intl to MidwayDiscover carefully curated flight deals from John F Kennedy Intl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 24, 2026.
Discover carefully curated flight deals from John F Kennedy Intl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 24, 2026.
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 9/51:14 pm
JFK
- MDW
1 stop4h 45m
Delta
Sun 9/66:05 am
MDW
- JFK
1 stop4h 54m
Delta
Deal found 6/22![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 10/16:00 am
JFK
- MDW
1 stop4h 07m
Delta
Mon 10/55:11 pm
MDW
- JFK
1 stop6h 48m
Delta
Deal found 6/23![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:00 am
JFK
- MDW
1 stop6h 15m
Delta
Sat 8/296:05 am
MDW
- JFK
1 stop6h 10m
Delta
Deal found 6/21![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:59 pm
JFK
- MDW
1 stop6h 34m
Delta
Mon 9/211:19 pm
MDW
- JFK
1 stop5h 50m
Delta
Deal found 6/23![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
JFK
- MDW
1 stop5h 05m
Delta
Tue 7/286:00 am
MDW
- JFK
1 stop5h 00m
Delta
Deal found 6/21![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/188:35 am
JFK
- MDW
1 stop8h 40m
Delta
Sun 8/236:05 am
MDW
- JFK
1 stop4h 54m
Delta
Deal found 6/22![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:59 pm
JFK
- MDW
1 stop4h 58m
Delta
Mon 9/149:24 am
MDW
- JFK
1 stop7h 06m
Delta
Deal found 6/21![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:14 pm
JFK
- MDW
1 stop6h 19m
Delta
Mon 8/105:10 pm
MDW
- JFK
1 stop7h 04m
Delta
Deal found 6/19![Delta logo]()
$361
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
JFK
- MDW
1 stop5h 09m
Delta
Tue 7/76:00 am
MDW
- JFK
1 stop5h 00m
Delta
Deal found 6/20![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/208:35 am
JFK
- MDW
1 stop8h 40m
Delta
Sun 8/236:05 am
MDW
- JFK
1 stop4h 54m
Delta
Deal found 6/23![Delta logo]()
$386
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/41:14 pm
JFK
- MDW
1 stop6h 19m
Delta
Sun 8/96:05 am
MDW
- JFK
1 stop4h 54m
Delta
Deal found 6/19![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/158:40 am
JFK
- MDW
1 stop7h 58m
Delta
Mon 8/246:05 am
MDW
- JFK
1 stop4h 54m
Delta
Deal found 6/23![Delta logo]()
$407
Last-minute flights from John F Kennedy Intl to MidwayDiscover last-minute flight deals from John F Kennedy Intl to Midway. Data last updated June 24, 2026 and is based on user searches.
Discover last-minute flight deals from John F Kennedy Intl to Midway. Data last updated June 24, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/41:40 pm
JFK
- MDW
1 stop7h 22m
Delta
Tue 7/141:18 pm
MDW
- JFK
1 stop4h 11m
Delta
Deal found 6/23![Delta logo]()
$361
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/712:59 pm
JFK
- MDW
1 stop6h 26m
Delta
Thu 7/161:18 pm
MDW
- JFK
1 stop4h 11m
Delta
Deal found 6/23![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/712:59 pm
JFK
- MDW
1 stop6h 26m
Delta
Wed 7/812:41 pm
MDW
- JFK
1 stop7h 48m
Delta
Deal found 6/23![Delta logo]()
$332
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/86:00 am
JFK
- MDW
1 stop5h 05m
Delta
Tue 7/141:18 pm
MDW
- JFK
1 stop4h 11m
Delta
Deal found 6/23![Delta logo]()
$302
This eDestinos deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/141:00 pm
JFK
- MDW
1 stop23h 07m
Frontier
Sun 7/196:05 am
MDW
- JFK
1 stop28h 45m
Frontier
Deal found 6/22![Frontier logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/161:00 pm
JFK
- MDW
1 stop10h 03m
Frontier
Sun 7/196:05 am
MDW
- JFK
1 stop28h 45m
Frontier
Deal found 6/23![Frontier logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/171:00 pm
JFK
- MDW
1 stop10h 03m
Frontier
Mon 7/206:05 am
MDW
- JFK
1 stop28h 45m
Frontier
Deal found 6/23![Frontier logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/181:00 pm
JFK
- MDW
1 stop10h 03m
Frontier
Mon 7/206:05 am
MDW
- JFK
1 stop28h 45m
Frontier
Deal found 6/23![Frontier logo]()
$339
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/2112:59 pm
JFK
- MDW
1 stop6h 26m
Delta
Tue 7/286:00 am
MDW
- JFK
1 stop5h 00m
Delta
Deal found 6/23![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/2112:59 pm
JFK
- MDW
1 stop6h 26m
Delta
Wed 7/296:00 am
MDW
- JFK
1 stop5h 00m
Delta
Deal found 6/24![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/226:00 am
JFK
- MDW
1 stop5h 05m
Delta
Wed 7/2912:41 pm
MDW
- JFK
1 stop6h 07m
Delta
Deal found 6/22![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:45 am
JFK
- MDW
1 stop11h 33m
Delta
Fri 8/141:25 pm
MDW
- JFK
1 stop5h 44m
Delta
Deal found 6/20![Delta logo]()
$346
One-way flights from John F Kennedy Intl to MidwaySearch for one-way flight options from John F Kennedy Intl to Midway. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
Search for one-way flight options from John F Kennedy Intl to Midway. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/121:00 pm
JFK
- MDW
1 stop9h 58m
Frontier
Deal found 6/23![Frontier logo]()
$132
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/51:00 pm
JFK
- MDW
1 stop10h 03m
Frontier
Deal found 6/23![Frontier logo]()
$133
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:00 pm
JFK
- MDW
1 stop10h 47m
Frontier
Deal found 6/21![Frontier logo]()
$134
This Frontier deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/221:00 pm
JFK
- MDW
1 stop10h 03m
Frontier
Deal found 6/23![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
JFK
- MDW
1 stop10h 47m
Frontier
Deal found 6/21![Frontier logo]()
$136
This Trip.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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.
Tue 8/181:00 pm
JFK
- MDW
1 stop10h 47m
Frontier
Deal found 6/24![Frontier logo]()
$138
This Trip.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/261:00 pm
JFK
- MDW
1 stop10h 47m
Frontier
Deal found 6/24![Frontier logo]()
$139
This Booking.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/161:00 pm
JFK
- MDW
1 stop10h 03m
Frontier
Deal found 6/23![Frontier logo]()
$140
This Trip.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/151:00 pm
JFK
- MDW
1 stop10h 03m
Frontier
Deal found 6/22![Frontier logo]()
$141
This Super.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:00 pm
JFK
- MDW
1 stop10h 47m
Frontier
Deal found 6/21![Frontier logo]()
$142
Find flight deals from John F Kennedy Intl to Midway
Discover tips and strategies to find the most affordable flight options for your journey from John F Kennedy Intl (JFK) to Midway (MDW). 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 June 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $283 (Kissandfly.com) |
One-way from | $132 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $322 |
Cheapflights Fare Finder
Customize your flight search to find flights from John F Kennedy Intl to Midway 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 June 24, 2026.
Use the filters below to find and compare flights from New York John F Kennedy Intl Airport to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Sat 9/5
1:14 pm-4:59 pm
1 stop4h 45m
Chicago Midway
Sun 9/6
6:05 am-11:59 am
1 stop4h 54m
$297
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Thu 10/1
6:00 am-9:07 am
1 stop4h 07m
Chicago Midway
Mon 10/5
5:11 pm-12:59 am
1 stop6h 48m
$297
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Tue 8/25
11:00 am-4:15 pm
1 stop6h 15m
Chicago Midway
Sat 8/29
6:05 am-1:15 pm
1 stop6h 10m
$297
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Thu 9/17
12:59 pm-6:33 pm
1 stop6h 34m
Chicago Midway
Mon 9/21
1:19 pm-8:09 pm
1 stop5h 50m
$297
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Wed 7/22
6:00 am-10:05 am
1 stop5h 05m
Chicago Midway
Tue 7/28
6:00 am-12:00 pm
1 stop5h 00m
$315
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Tue 8/18
8:35 am-4:15 pm
1 stop8h 40m
Chicago Midway
Sun 8/23
6:05 am-11:59 am
1 stop4h 54m
$357
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Fri 9/11
12:59 pm-4:57 pm
1 stop4h 58m
Chicago Midway
Mon 9/14
9:24 am-5:30 pm
1 stop7h 06m
$357
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Thu 8/6
1:14 pm-6:33 pm
1 stop6h 19m
Chicago Midway
Mon 8/10
5:10 pm-1:14 am
1 stop7h 04m
$361
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Sat 7/4
6:00 am-10:09 am
1 stop5h 09m
Chicago Midway
Tue 7/7
6:00 am-12:00 pm
1 stop5h 00m
$362
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Thu 8/20
8:35 am-4:15 pm
1 stop8h 40m
Chicago Midway
Sun 8/23
6:05 am-11:59 am
1 stop4h 54m
$386
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from John F Kennedy Intl to Midway
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 Midway in June.
| 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 |
- Most accurate provider: When it comes to deals on New York John F Kennedy Intl Airport-Chicago Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from John F Kennedy Intl with our price prediction graph.
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 Midway Airport
How often are flights from New York to Chicago delayed?
About 33% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 149 minutes.
What is the most punctual flight time for New York to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Friday tends to have the lowest number of delays on this route, whereas Thursday 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 36% of flights being delayed.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated June 24, 2026.
Read reviews from past customers who have flown Delta from New York John F Kennedy Intl Airport to Chicago Midway Airport. 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.
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
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 Midway. 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 Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Midway
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John F Kennedy Intl and Midway flights
Browse other John F Kennedy Intl and Midway flight options. Last updated on June 24, 2026.
Other flights from John F Kennedy Intl
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Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from John F Kennedy Intl to Midway
Discover the top airline that operate flights from John F Kennedy Intl to Midway. 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 June 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$203 | Average$350 | FlexibilityNo cancel fee | On-timeN/A |