JFK - MDW

$133 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 7/18. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$278
Frontier
Sat 8/8Mon 8/10
JFK - MDW • 1 stop
Cheapest one-way
$133
Typical prices: $218-$378
Frontier
Sat 7/18
JFK - MDW • 1 stop
Top airlines
Frontier
Cheapest • from $278 (round-trip)
Delta
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
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Insights
Top layover airports
Atlanta (ATL)
Cheapest • Avg $179 (round-trip)
Detroit (DTW)
Shortest trip • 6h 31m (one-way)
Insights
Insights
Insights
Insights
Avoid delays
Delta
Most punctual • 64% on-time
Night flights
Best time • Fewest delays
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
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

Sat, Aug 8 - Mon, Aug 10
Frontier Logo
1:00 pm - 10:03 pm
JFK
-
MDW
10h 03m
1 stop
Frontier Logo
6:05 am - 11:59 am
MDW
-
JFK
4h 54m
1 stop
$278Frontier
Sat, Aug 8 - Mon, Aug 10
Frontier Logo
1:00 pm - 10:03 pm
JFK
-
MDW
10h 03m
1 stop
Frontier Logo
6:05 am - 11:59 am
MDW
-
JFK
4h 54m
1 stop
$281Frontier
Tue, Sep 15 - Wed, Sep 23
Delta Logo
7:15 am - 12:34 pm
JFK
-
MDW
6h 19m
1 stop
Delta Logo
1:14 pm - 8:04 pm
MDW
-
JFK
5h 50m
1 stop
$293Delta
Fri, Sep 18 - Wed, Sep 23
Delta Logo
7:15 am - 12:34 pm
JFK
-
MDW
6h 19m
1 stop
Delta Logo
1:14 pm - 8:04 pm
MDW
-
JFK
5h 50m
1 stop
$295Delta
Fri, Sep 18 - Sun, Sep 20
Delta Logo
7:15 am - 12:34 pm
JFK
-
MDW
6h 19m
1 stop
Delta Logo
5:10 pm - 12:59 am
MDW
-
JFK
6h 49m
1 stop
$297Delta
Wed, Jul 8 - Thu, Jul 16
Delta Logo
6:00 am - 10:05 am
JFK
-
MDW
5h 05m
1 stop
Delta Logo
1:18 pm - 6:29 pm
MDW
-
JFK
4h 11m
1 stop
$302Delta
Wed, Sep 16 - Fri, Sep 18
Delta Logo
12:00 pm - 6:11 pm
JFK
-
MDW
7h 11m
1 stop
Delta Logo
5:10 pm - 12:59 am
MDW
-
JFK
6h 49m
1 stop
$304Delta
Sun, Sep 6 - Thu, Sep 10
Delta Logo
8:35 am - 3:44 pm
JFK
-
MDW
8h 09m
1 stop
Delta Logo
4:30 pm - 12:59 am
MDW
-
JFK
7h 29m
1 stop
$306Delta
Sun, Sep 13 - Sat, Sep 19
Delta Logo
7:45 am - 1:11 pm
JFK
-
MDW
6h 26m
1 stop
Delta Logo
1:14 pm - 8:04 pm
MDW
-
JFK
5h 50m
1 stop
$310Delta
Wed, Aug 5 - Sat, Aug 8
Delta Logo
8:35 am - 10:36 pm
JFK
-
MDW
15h 01m
2 stops
Delta Logo
4:39 pm - 1:14 am
MDW
-
JFK
7h 35m
1 stop
$313Delta
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 Frontier ($278) and Delta ($293).

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 $203.

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Good to know

Cheapest flight$133
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 $133 for a one-way ticket and $278 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 8424 reviews
7.8Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

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.

8.0 ExcellentAnonymous, Jun 2026
JFK - ATL
Read more Delta reviews

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!

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

I am still at the Airport! Delayed Delayed and Delyaed

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

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

Information on your arrival and departure airports

New York John F Kennedy Airport (JFK)
Midway (MDW)