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$82+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 September 16, 2025.

Round-trip from

$146
(Booking.com)

One-way from

$82
(Frontier)

Popular in

December

Cheapest in

May

Average price

$229
From New York John F Kennedy Intl to Chicago Midway
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One-way flight from New York John F Kennedy Intl to Chicago Midway
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Highest demand for flights based on searches. 21% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from John F Kennedy Intl to Midway

Cheapest flights from John F Kennedy Intl to Midway
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 September 16, 2025.

This Booking.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Tue 10/286:25 amJFK - MDW
1 stop6h 13mFrontier
Wed 11/52:06 pmMDW - JFK
1 stop9h 27mFrontier
Deal found 9/15$146
This Priceline deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:01 pmJFK - MDW
1 stop8h 20mFrontier
Sun 10/269:26 pmMDW - JFK
1 stop9h 02mFrontier
Deal found 9/14$147
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Sat 11/19:00 amJFK - MDW
1 stop10h 39mFrontier
Mon 11/31:37 pmMDW - JFK
1 stop9h 56mFrontier
Deal found 9/14$148
This Booking.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Sat 11/810:00 amJFK - MDW
1 stop9h 39mFrontier
Sun 11/910:12 amMDW - JFK
1 stop23h 17mFrontier
Deal found 9/15$149
This Gotogate deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/19:00 amJFK - MDW
1 stop10h 39mFrontier
Sun 11/210:12 amMDW - JFK
1 stop23h 17mFrontier
Deal found 9/14$156
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/219:00 amJFK - MDW
1 stop5h 38mFrontier
Thu 10/239:26 pmMDW - JFK
1 stop9h 02mFrontier
Deal found 9/14$158
This Priceline deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/249:00 amJFK - MDW
1 stop7h 58mFrontier
Fri 9/265:15 pmMDW - JFK
1 stop6h 53mFrontier
Deal found 9/14$164
This Flightnetwork deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2612:59 pmJFK - MDW
1 stop8h 53mFrontier
Sat 9/2710:51 amMDW - JFK
1 stop22h 35mFrontier
Deal found 9/14$165
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Fri 9/269:00 amJFK - MDW
1 stop8h 00mFrontier
Mon 9/295:15 pmMDW - JFK
1 stop6h 53mFrontier
Deal found 9/14$166
This FlightHub deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/251:01 pmJFK - MDW
1 stop10h 46mFrontier
Sat 11/11:37 pmMDW - JFK
1 stop9h 56mFrontier
Deal found 9/15$167
This Booking.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/166:20 amJFK - MDW
1 stop18h 26mFrontier
Tue 10/218:05 amMDW - JFK
1 stop26h 54mFrontier
Deal found 9/16$168

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 September 16, 2025.
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

John F Kennedy Intl

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 10/27

1:01 pm-11:46 pm

1 stop11h 45m

Chicago Midway

Wed 10/29

2:06 pm-12:33 am

1 stop9h 27m

$147

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 11/1

9:00 am-6:39 pm

1 stop10h 39m

Chicago Midway

Mon 11/3

1:37 pm-12:33 am

1 stop9h 56m

$147

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 10/3

9:00 am-4:00 pm

1 stop8h 00m

Chicago Midway

Mon 10/6

5:33 pm-1:08 am

1 stop6h 35m

$147

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 10/20

1:01 pm-11:46 pm

1 stop11h 45m

Chicago Midway

Fri 10/24

12:18 pm-1:46 am

1 stop12h 28m

$180

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 10/16

7:20 am-6:25 pm

1 stop12h 05m

Chicago Midway

Mon 10/20

6:23 pm-9:00 am

1 stop13h 37m

$284

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 10/21

12:59 pm-6:25 pm

1 stop6h 26m

Chicago Midway

Wed 10/22

5:04 pm-12:56 am

1 stop6h 52m

$297

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 10/11

12:59 pm-6:25 pm

1 stop6h 26m

Chicago Midway

Wed 10/15

10:35 am-8:00 pm

1 stop8h 25m

$297

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 11/21

10:15 am-4:38 pm

1 stop7h 23m

Chicago Midway

Sun 11/23

5:34 pm-1:08 am

1 stop6h 34m

$297

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 10/4

7:00 am-1:03 pm

1 stop7h 03m

Chicago Midway

Mon 10/6

6:23 pm-11:18 pm

1 stop3h 55m

$297

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 10/23

1:01 pm-8:21 pm

1 stop8h 20m

$82

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 20 results
1
2

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.
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

What is the cheapest month to book a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport?

Currently, April 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 $160). Flying from New York John F Kennedy Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

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 September 16, 2025.
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.
Delta
8.0
Very good
7,957 reviews

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • How long is the flight from New York John F Kennedy Intl Airport to Chicago Midway Airport?

    Departing from New York John F Kennedy Intl Airport to Chicago Midway Airport will take you 11h 45m. There are 729 mi between New York John F Kennedy Intl Airport and Chicago Midway Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from New York John F Kennedy Intl Airport to Chicago Midway Airport round-trip?

    Flying on Delta is currently your cheapest option to Chicago Midway Airport, with prices starting at $296. Delta is currently priced 23% below the average price you’ll pay for this route.

  • Can I find deals for flights from John F Kennedy Intl to Midway that include hotel bookings?

    Yes. In addition to deals on John F Kennedy Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from John F Kennedy Intl to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from John F Kennedy Intl to Midway.

  • Can I find deals for business class flights from John F Kennedy Intl to Midway?

    Yes. Cheapflights offers flight deals from John F Kennedy Intl to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport?

    Currently, April 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 $160). Flying from New York John F Kennedy Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$296Average$417FlexibilityNo cancel feeOn-timeN/A

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