$64+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Apr 25 — May 21
Round-trip
1 adult, Economy
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Find cheap flights from John F Kennedy Intl to Midway 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 John F Kennedy Intl to Midway
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Last-minute
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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 March 26, 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 March 26, 2026.
This Expedia deal was found by Cheapflights users on 3/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:30 am
JFK
- MDW
1 stop11h 49m
Frontier
Thu 4/92:56 pm
MDW
- JFK
1 stop9h 24m
Frontier
Deal found 3/24![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:00 pm
JFK
- MDW
1 stop10h 19m
Frontier
Tue 4/216:10 am
MDW
- JFK
1 stop28h 40m
Frontier
Deal found 3/26![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:00 pm
JFK
- MDW
1 stop6h 37m
Frontier
Mon 4/202:15 pm
MDW
- JFK
1 stop20h 35m
Frontier
Deal found 3/26![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:00 pm
JFK
- MDW
1 stop10h 19m
Frontier
Tue 4/282:15 pm
MDW
- JFK
1 stop20h 35m
Frontier
Deal found 3/25![Frontier logo]()
$193
This Frontier deal was found by Cheapflights users on 3/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3111:00 am
JFK
- MDW
1 stop10h 54m
Frontier
Thu 4/92:56 pm
MDW
- JFK
1 stop9h 24m
Frontier
Deal found 3/24![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Wed 6/106:00 am
MDW
- JFK
1 stop28h 51m
Frontier
Deal found 3/25![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Tue 4/211:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Tue 4/282:15 pm
MDW
- JFK
1 stop20h 35m
Frontier
Deal found 3/23![Frontier logo]()
$210
This Orbitz deal was found by Cheapflights users on 3/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/411:30 am
JFK
- MDW
1 stop9h 37m
Frontier
Tue 4/72:56 pm
MDW
- JFK
1 stop9h 24m
Frontier
Deal found 3/21![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Sat 5/27:34 pm
MDW
- JFK
1 stop15h 16m
Frontier
Deal found 3/25![Frontier logo]()
$216
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 March 26, 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 March 26, 2026.
This Delta deal was found by Cheapflights users on 3/22. 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 5/2612:59 pm
JFK
- MDW
1 stop6h 34m
Delta
Fri 5/295:08 pm
MDW
- JFK
1 stop6h 58m
Delta
Deal found 3/22![Delta logo]()
$293
This Delta deal was found by Cheapflights users on 3/23. 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 5/57:08 am
JFK
- MDW
1 stop6h 35m
Delta
Tue 5/125:10 pm
MDW
- JFK
1 stop6h 56m
Delta
Deal found 3/23![Delta logo]()
$293
This Delta deal was found by Cheapflights users on 3/21. 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 4/173:55 pm
JFK
- MDW
1 stop7h 33m
Delta
Tue 4/215:21 pm
MDW
- JFK
1 stop6h 27m
Delta
Deal found 3/21![Delta logo]()
$293
This Delta deal was found by Cheapflights users on 3/22. 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 5/1311:10 am
JFK
- MDW
1 stop6h 02m
Delta
Sat 5/165:10 pm
MDW
- JFK
1 stop6h 56m
Delta
Deal found 3/22![Delta logo]()
$293
This Delta deal was found by Cheapflights users on 3/22. 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.
Thu 4/1612:59 pm
JFK
- MDW
1 stop5h 59m
Delta
Mon 4/201:24 pm
MDW
- JFK
1 stop4h 21m
Delta
Deal found 3/22![Delta logo]()
$293
This Delta deal was found by Cheapflights users on 3/26. 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.
Sat 4/1812:59 pm
JFK
- MDW
1 stop5h 59m
Delta
Mon 4/201:24 pm
MDW
- JFK
1 stop4h 21m
Delta
Deal found 3/26![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:20 am
JFK
- MDW
1 stop6h 22m
Delta
Wed 5/275:12 pm
MDW
- JFK
1 stop6h 54m
Delta
Deal found 3/25![Delta logo]()
$295
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:31 am
JFK
- MDW
1 stop8h 05m
Delta
Sat 5/95:10 pm
MDW
- JFK
1 stop6h 56m
Delta
Deal found 3/25![Delta logo]()
$295
This Delta deal was found by Cheapflights users on 3/24. 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.
Sat 6/1312:59 pm
JFK
- MDW
1 stop6h 07m
Delta
Tue 6/235:11 pm
MDW
- JFK
1 stop6h 57m
Delta
Deal found 3/24![Delta logo]()
$302
Last-minute flights from John F Kennedy Intl to MidwayDiscover last-minute flight deals from John F Kennedy Intl to Midway. Data last updated March 26, 2026 and is based on user searches.
Discover last-minute flight deals from John F Kennedy Intl to Midway. Data last updated March 26, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3111:00 am
JFK
- MDW
1 stop10h 54m
Frontier
Thu 4/92:56 pm
MDW
- JFK
1 stop9h 24m
Frontier
Deal found 3/24![Frontier logo]()
$201
This Orbitz deal was found by Cheapflights users on 3/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/411:30 am
JFK
- MDW
1 stop9h 37m
Frontier
Tue 4/72:56 pm
MDW
- JFK
1 stop9h 24m
Frontier
Deal found 3/21![Frontier logo]()
$215
This Expedia deal was found by Cheapflights users on 3/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:30 am
JFK
- MDW
1 stop11h 49m
Frontier
Thu 4/92:56 pm
MDW
- JFK
1 stop9h 24m
Frontier
Deal found 3/24![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Mon 4/202:15 pm
MDW
- JFK
1 stop20h 35m
Frontier
Deal found 3/26![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:00 pm
JFK
- MDW
1 stop10h 19m
Frontier
Tue 4/216:10 am
MDW
- JFK
1 stop28h 40m
Frontier
Deal found 3/26![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:00 pm
JFK
- MDW
1 stop10h 14m
Frontier
Mon 4/202:15 pm
MDW
- JFK
1 stop20h 35m
Frontier
Deal found 3/26![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Tue 4/211:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Tue 4/282:15 pm
MDW
- JFK
1 stop20h 35m
Frontier
Deal found 3/23![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:00 pm
JFK
- MDW
1 stop10h 19m
Frontier
Tue 4/282:15 pm
MDW
- JFK
1 stop20h 35m
Frontier
Deal found 3/25![Frontier logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Sat 5/27:34 pm
MDW
- JFK
1 stop15h 16m
Frontier
Deal found 3/25![Frontier logo]()
$216
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 March 26, 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 March 26, 2026.
This iWofly deal was found by Cheapflights users on 3/25. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Deal found 3/25![Frontier logo]()
$64
This Super.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/211:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Deal found 3/26![Frontier logo]()
$69
This iWofly deal was found by Cheapflights users on 3/26. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Deal found 3/26![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 3/21. 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.
Tue 4/141:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Deal found 3/21![Frontier logo]()
$71
This Trip.com deal was found by Cheapflights users on 3/25. 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.
Wed 4/151:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Deal found 3/25![Frontier logo]()
$73
This Trip.com deal was found by Cheapflights users on 3/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Deal found 3/26![Frontier logo]()
$74
This Super.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/171:00 pm
JFK
- MDW
1 stop10h 26m
Frontier
Deal found 3/25![Frontier logo]()
$75
This iWofly deal was found by Cheapflights users on 3/25. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:00 pm
JFK
- MDW
1 stop6h 37m
Frontier
Deal found 3/25![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:30 am
JFK
- MDW
1 stop27h 31m
Frontier
Deal found 3/24![Frontier logo]()
$86
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 March 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $152 (Kiwi.com) |
One-way from | $64 (iWofly) |
Popular in | October |
Cheapest in | May |
Average price | $228 |
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 March 26, 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
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Tue 5/26
12:59 pm-6:33 pm
1 stop6h 34m
Chicago Midway
Fri 5/29
5:08 pm-1:06 am
1 stop6h 58m
$293
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Tue 5/5
7:08 am-12:43 pm
1 stop6h 35m
Chicago Midway
Tue 5/12
5:10 pm-1:06 am
1 stop6h 56m
$293
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Fri 4/17
3:55 pm-10:28 pm
1 stop7h 33m
Chicago Midway
Tue 4/21
5:21 pm-12:48 am
1 stop6h 27m
$293
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Wed 5/13
11:10 am-4:12 pm
1 stop6h 02m
Chicago Midway
Sat 5/16
5:10 pm-1:06 am
1 stop6h 56m
$293
Quickest round-trip
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Thu 4/16
12:59 pm-5:58 pm
1 stop5h 59m
Chicago Midway
Mon 4/20
1:24 pm-6:45 pm
1 stop4h 21m
$293
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Sat 4/18
12:59 pm-5:58 pm
1 stop5h 59m
Chicago Midway
Mon 4/20
1:24 pm-6:45 pm
1 stop4h 21m
$294
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Sat 5/23
7:20 am-12:42 pm
1 stop6h 22m
Chicago Midway
Wed 5/27
5:12 pm-1:06 am
1 stop6h 54m
$295
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Wed 5/6
11:31 am-6:36 pm
1 stop8h 05m
Chicago Midway
Sat 5/9
5:10 pm-1:06 am
1 stop6h 56m
$295
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Sat 6/13
12:59 pm-6:06 pm
1 stop6h 07m
Chicago Midway
Tue 6/23
5:11 pm-1:08 am
1 stop6h 57m
$302
Cheapest one-way
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Sun 5/24
7:20 am-12:42 pm
1 stop6h 22m
$147
Showing 1-10 of 19 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 March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
Prices
Delays
What is the cheapest month to book a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport?
Currently, May is the cheapest month in which you can book a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport (average of $55). Flying from New York John F Kennedy Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of $636). 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.
How much does it cost to fly round-trip from New York John F Kennedy Intl Airport to Chicago Midway Airport?
How often are flights from New York to Chicago delayed?
About 30% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 158 minutes.
What is the most punctual flight time for New York to Chicago flights?
Historically, flights departing in the evening are less likely to be delayed, whereas flights leaving in the early afternoon 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 37% 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 March 26, 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.
Food
7.2
Entertainment
7.8
Overall
7.9
Boarding
8.1
Comfort
7.9
Crew
8.5
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Food
7.2
Entertainment
7.8
Overall
7.9
Boarding
8.1
Comfort
7.9
Crew
8.5
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 March 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$203 | Average$350 | FlexibilityNo cancel fee | On-timeN/A |