JFK - MDW

$120 Find Cheap Flights from New York John F Kennedy Airport to Chicago Midway Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from John F Kennedy Intl to Midway departing on 9/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$297
Delta
Wed 9/23Wed 9/30
JFK - MDW • 1 stop
Cheapest one-way
$120
Frontier
Wed 9/16
JFK - MDW • 1 stop
Top airlines
Cheapest • from $297 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between John F Kennedy Intl and Midway. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $296 (round-trip)
Shortest trip • 5h 38m (one-way)
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We hope you love your trip to Midway!
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Flight Deals

Cheap Flights from John F Kennedy Intl to Midway (JFK-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from John F Kennedy Intl to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from John F Kennedy Intl to Midway

Wed, Sep 23 - Wed, Sep 30
Delta Logo
12:00 pm - 6:19 pmJFK  New York John F Kennedy Intl-MDW Chicago Midway
7h 19m1 stop Minneapolis St Paul
Delta Logo
1:19 pm - 8:09 pmMDW  Chicago Midway-JFK New York John F Kennedy Intl
5h 50m1 stop Detroit Metropolitan Wayne County
$297Delta
Wed, Sep 23 - Fri, Sep 25
Delta Logo
12:00 pm - 6:19 pmJFK  New York John F Kennedy Intl-MDW Chicago Midway
7h 19m1 stop Minneapolis St Paul
Delta Logo
5:10 pm - 12:59 amMDW  Chicago Midway-JFK New York John F Kennedy Intl
6h 49m1 stop Atlanta Hartsfield-Jackson
$297Delta
Fri, Oct 2 - Mon, Oct 5
Delta Logo
1:00 pm - 6:33 pmJFK  New York John F Kennedy Intl-MDW Chicago Midway
6h 33m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:10 pm - 12:59 amMDW  Chicago Midway-JFK New York John F Kennedy Intl
6h 49m1 stop Atlanta Hartsfield-Jackson
$297Delta
Thu, Oct 1 - Sat, Oct 3
Delta Logo
6:00 am - 9:07 amJFK  New York John F Kennedy Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:19 pm - 8:09 pmMDW  Chicago Midway-JFK New York John F Kennedy Intl
5h 50m1 stop Detroit Metropolitan Wayne County
$297Delta
Sat, Sep 5 - Tue, Sep 8
Delta Logo
9:45 am - 3:44 pmJFK  New York John F Kennedy Intl-MDW Chicago Midway
6h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:30 pm - 12:59 amMDW  Chicago Midway-JFK New York John F Kennedy Intl
7h 29m1 stop Atlanta Hartsfield-Jackson
$297Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
8:35 am - 4:15 pmJFK  New York John F Kennedy Intl-MDW Chicago Midway
8h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:24 am - 5:48 pmMDW  Chicago Midway-JFK New York John F Kennedy Intl
7h 24m1 stop Detroit Metropolitan Wayne County
$297Delta
Sat, Sep 26 - Wed, Sep 30
Delta Logo
11:15 am - 3:24 pmJFK  New York John F Kennedy Intl-MDW Chicago Midway
5h 09m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:19 pm - 8:09 pmMDW  Chicago Midway-JFK New York John F Kennedy Intl
5h 50m1 stop Detroit Metropolitan Wayne County
$297Delta
Sat, Oct 24 - Sat, Oct 24
Delta Logo
6:00 am - 10:37 amJFK  New York John F Kennedy Intl-MDW Chicago Midway
5h 37m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:31 pm - 11:58 pmMDW  Chicago Midway-JFK New York John F Kennedy Intl
5h 27m1 stop Minneapolis St Paul
$297Delta
Fri, Sep 25 - Mon, Sep 28
Frontier Logo
1:00 pm - 5:51 pmJFK  New York John F Kennedy Intl-MDW Chicago Midway
5h 51m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:46 pm - 11:50 amMDW  Chicago Midway-JFK New York John F Kennedy Intl
16h 04m1 stop Atlanta Hartsfield-Jackson
$344Frontier
Fri, Sep 11 - Mon, Sep 14
Frontier Logo
1:00 pm - 5:51 pmJFK  New York John F Kennedy Intl-MDW Chicago Midway
5h 51m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:54 pm - 11:50 amMDW  Chicago Midway-JFK New York John F Kennedy Intl
21h 56m2 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson
$374Frontier
Booking Insights

KAYAK's insights & trends for John F Kennedy Intl to Midway flights

Get data-powered insights and trends into flights from John F Kennedy Intl to Midway to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from New York John F Kennedy Airport to Chicago Midway Airport?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from New York John F Kennedy Airport to Chicago Midway Airport were found on Delta ($297) and Frontier ($344).

Which airlines fly non-stop between New York John F Kennedy Intl Airport and Chicago Midway Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from New York John F Kennedy Intl Airport to Chicago Midway Airport.

There is just one airline that flies from New York John F Kennedy Intl Airport to Chicago Midway Airport direct and that is Delta. The best round-trip deal found from Delta for the route is $296.

Good to know

Cheapest flight

$120
Flight from New York John F Kennedy Airport to Chicago Midway Airport

When to book flights from John F Kennedy Intl to Midway

Are your dates flexible? Find out the best times to travel from John F Kennedy Intl to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking New York John F Kennedy Airport to Chicago Midway Airport flights

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

    In the last 5 days, the lowest price for a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport was $120 for a one-way ticket and $297 for a round-trip.

  • Do I need a passport to fly between New York John F Kennedy Airport and Chicago Midway Airport?

    No, a passport isn't needed to fly from New York John F Kennedy Airport to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from New York John F Kennedy Airport to Chicago Midway Airport?

    On your way to Chicago Midway Airport, you’ll fly out from New York John F Kennedy Intl. You’ll be landing at Chicago Midway.

  • Which aircraft models fly most regularly from New York John F Kennedy Airport to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from New York John F Kennedy Airport to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between New York John F Kennedy Airport and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from New York John F Kennedy Airport to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York John F Kennedy Airport to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York John F Kennedy Airport to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from New York John F Kennedy Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from New York John F Kennedy Airport to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to New York John F Kennedy Airport with another airline. Booking your flights between New York John F Kennedy Airport and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York John F Kennedy Airport to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from New York John F Kennedy Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from John F Kennedy Intl to Midway

 
See real verified KAYAK customer reviews for airlines flying from New York to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from John F Kennedy Intl to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8491 reviews
7.8Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

6.0 GoodLaura, Jul 2026
Read more Delta reviews

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

Our flight was delayed multiple times and then canceled at almost 1 in the morning. We are a family of 7, traveling with 5 young children. When the flight we were supposed to fly on finally arrived after waiting all day after an international flight into JFK we were informed our flight was in need of a copilot and once they located one we would take off. Then our flight was cancelled because the copilot was over his hours and they couldn't locate another. They knew before taking off from the previous location that the copilot would be unable to fly. They could have communicated the cancellation of the flight hours in advance. Once they cancelled and the pilot and copilot got off the flight, they joked about it. While there are understandably limits on flight time for pilots, they can still handle the situation in a professional manner. The late cancellation resulted in angry passengers that required police intervention in the airport. It also occurred so late and included other delta flights that after trying 15 different hotels, we were unable to secure a hotel room, they were all booked. No rental cars were available in the area either. We ended up staying in the airport with the 5 children. We made it home after 54 hours of travel with maybe 2 hours of sleep. Our luggage was lost and had to be claimed at the airport at our final destination. This was the worst trip I have ever taken and the worst airport I have ever spent time in. I met two individuals in the airport that were kind and helpful; Tonya Maingot Williams from the can we hel desk that worked to help get us rebooked and home, as well as provide us with care bags for our extended stay in the airport. The other individual was Danielle from Buffalo Wild Wings that was so very kind when we found a place to take our family we were traveling with to eat, all 11 of us and we were able to sit down together to enjoy a meal during such a stressful time.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Was revoked with Jet Blue due to delay from Kenya Air

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Got on the plane and sat there for an hour before departure.

Cramped seating for me. Luckily it wasn’t a long flight

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

Everything you need to know for your flight from John F Kennedy Intl to Midway

Information on your arrival and departure airports