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$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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Feb 24 — Mar 31
Tue 2/24
Tue 3/3
1 adult, Economy
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Cheap 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 January 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:00 am
JFK
-
MDW
1 stop14h 07m
Frontier
Wed 2/187:00 am
MDW
-
JFK
1 stop17h 03m
Frontier
Deal found 1/22$150
This Frontier deal was found by Cheapflights users on 1/24. 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.
Sat 2/211:00 pm
JFK
-
MDW
1 stop9h 33m
Frontier
Sat 2/288:00 am
MDW
-
JFK
1 stop6h 29m
Frontier
Deal found 1/24$154
This Frontier deal was found by Cheapflights users on 1/23. 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.
Sat 2/211:00 pm
JFK
-
MDW
1 stop9h 33m
Frontier
Mon 2/232:19 pm
MDW
-
JFK
1 stop9h 44m
Frontier
Deal found 1/23$160
This Frontier deal was found by Cheapflights users on 1/24. 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.
Thu 2/261:00 pm
JFK
-
MDW
1 stop10h 29m
Frontier
Sat 2/288:00 am
MDW
-
JFK
1 stop6h 29m
Frontier
Deal found 1/24$161
This Flightnetwork deal was found by Cheapflights users on 1/24. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
JFK
-
MDW
1 stop6h 27m
Frontier
Mon 2/232:19 pm
MDW
-
JFK
1 stop9h 44m
Frontier
Deal found 1/24$167
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Sun 2/810:02 am
JFK
-
MDW
2 stops26h 43m
Multiple Airlines
Thu 2/126:25 am
MDW
-
JFK
1 stop17h 38m
Multiple Airlines
Deal found 1/24$169
This Travelocity deal was found by Cheapflights users on 1/24. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:02 am
JFK
-
MDW
1 stop27h 39m
Frontier
Tue 4/72:56 pm
MDW
-
JFK
1 stop9h 24m
Frontier
Deal found 1/24$175

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 January 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$150
(Kiwi.com)

One-way from

$64
(Frontier)

Popular in

October

Cheapest in

May

Average price

$159
Provider with most accurate pricing for New York John F Kennedy Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for New York John F Kennedy Intl-Chicago Midway flights.
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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. 30% potential increase in price ($154 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 25, 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

John F Kennedy Intl

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 4/25

11:30 am-7:31 pm

1 stop9h 01m

Chicago Midway

Sat 5/2

2:20 pm-12:59 am

1 stop9h 39m

$160

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 4/25

11:30 am-7:31 pm

1 stop9h 01m

Chicago Midway

Mon 4/27

9:14 am-11:50 am

1 stop25h 36m

$160

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 2/27

1:00 pm-6:38 pm

1 stop6h 38m

Chicago Midway

Sun 3/1

9:04 pm-1:03 am

1 stop26h 59m

$172

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 5/14

1:00 pm-8:04 am

1 stop20h 04m

Chicago Midway

Fri 5/15

2:20 pm-12:59 am

1 stop9h 39m

$195

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 3/20

10:00 am-7:47 pm

1 stop10h 47m

Chicago Midway

Mon 3/23

9:51 pm-12:16 pm

1 stop13h 25m

$229

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 4/6

11:30 am-8:07 pm

1 stop9h 37m

Chicago Midway

Thu 4/9

2:56 pm-1:20 am

1 stop9h 24m

$251

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 2/14

6:29 am-12:46 pm

1 stop7h 17m

Chicago Midway

Wed 2/18

6:40 pm-12:50 am

1 stop5h 10m

$291

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 2/23

12:32 pm-5:45 pm

1 stop6h 13m

Chicago Midway

Sat 2/28

5:00 pm-11:40 pm

1 stop5h 40m

$294

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 2/14

6:29 am-12:46 pm

1 stop7h 17m

Chicago Midway

Mon 2/16

1:26 pm-6:51 pm

1 stop4h 25m

$294

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 2/20

7:00 am-12:46 pm

1 stop6h 46m

Chicago Midway

Mon 2/23

10:49 am-6:20 pm

1 stop6h 31m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 21 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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, 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.

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 January 25, 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.
Delta
7.9
Good
8,111 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.8

Comfort

7.9

Overall

7.9

Food

7.2

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
7.9
Good
8,111 reviews
Delta
7.9
Good
8,111 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.8

Comfort

7.9

Overall

7.9

Food

7.2

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 9h 01m. There are 729 mi between New York John F Kennedy Intl Airport and Chicago Midway Airport.

  • 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 13% 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, 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.

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
Lansing
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 January 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$296Average$350FlexibilityNo cancel feeOn-timeN/A

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