JFK - MDW

$88 Find Cheap Flights from New York John F Kennedy Airport to Chicago Midway Airport

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 5/30. 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
$169
Frontier
Tue 8/18Wed 8/26
JFK - MDW • 1 stop
Cheapest one-way
$88
Typical prices: $165-$276
Frontier
Sat 5/30
JFK - MDW • 1 stop
Top airlines
Cheapest • from $169 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
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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
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Insights
Top layover airports
Cheapest • Avg $179 (round-trip)
Shortest trip • 6h 31m (one-way)
Insights
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Avoid delays
Most punctual • 63% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Tue, Aug 18 - Wed, Aug 26
Frontier Logo
1:00 pm - 10:11 pm
JFK
-
MDW
10h 11m
1 stop
Frontier Logo
12:04 pm - 11:51 am
MDW
-
JFK
22h 47m
1 stop
$169Frontier
Tue, May 26 - Fri, May 29
Frontier Logo
1:00 pm - 10:02 pm
JFK
-
MDW
10h 02m
1 stop
Frontier Logo
12:04 pm - 11:39 am
MDW
-
JFK
22h 35m
1 stop
$174Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
1:00 pm - 10:02 pm
JFK
-
MDW
10h 02m
1 stop
Frontier Logo
6:00 am - 11:39 am
MDW
-
JFK
28h 39m
1 stop
$187Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
1:00 pm - 10:02 pm
JFK
-
MDW
10h 02m
1 stop
Frontier Logo
6:00 am - 11:39 am
MDW
-
JFK
28h 39m
1 stop
$188Frontier
Wed, Jun 24 - Mon, Jun 29
Frontier Logo
1:05 pm - 10:11 pm
JFK
-
MDW
10h 06m
1 stop
Frontier Logo
12:04 pm - 11:51 am
MDW
-
JFK
22h 47m
1 stop
$191Frontier
Tue, Jun 2 - Tue, Jun 9
Frontier Logo
1:00 pm - 10:02 pm
JFK
-
MDW
10h 02m
1 stop
Frontier Logo
12:27 pm - 11:59 am
MDW
-
JFK
22h 32m
1 stop
$217Frontier
Thu, Jun 4 - Wed, Jun 10
Frontier Logo
1:00 pm - 10:02 pm
JFK
-
MDW
10h 02m
1 stop
Frontier Logo
6:00 am - 11:51 am
MDW
-
JFK
28h 51m
1 stop
$222Frontier
Wed, Jun 3 - Tue, Jun 9
Frontier Logo
1:00 pm - 10:02 pm
JFK
-
MDW
10h 02m
1 stop
Frontier Logo
6:00 am - 11:59 am
MDW
-
JFK
28h 59m
1 stop
$229Frontier
Fri, Jun 5 - Wed, Jun 10
Frontier Logo
1:00 pm - 11:04 am
JFK
-
MDW
23h 04m
1 stop
Frontier Logo
12:04 pm - 11:51 am
MDW
-
JFK
22h 47m
1 stop
$232Frontier
Wed, Jun 3 - Tue, Jun 9
Frontier Logo
1:00 pm - 10:02 pm
JFK
-
MDW
10h 02m
1 stop
Frontier Logo
6:00 am - 11:59 am
MDW
-
JFK
28h 59m
1 stop
$234Frontier
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.

How much is a round-trip flight from New York John F Kennedy Intl Airport to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport departing in August.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New York John F Kennedy Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from New York John F Kennedy Intl Airport to Chicago Midway Airport is March, where tickets cost $0 (return) on average. On the other hand, the most expensive months are October and November, where the average cost of round-trip tickets is $636 and $624 respectively.

Good to know

Low seasonMay
Cheapest flight$88
Best time to beat the crowds with an average 74% drop in price.
Most popular time to fly with an average 8% increase in price.
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 3 days, the lowest price for a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport was $88 for a one-way ticket and $169 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.
7.9
DeltaOverall score based on 8456 reviews
8.1Boarding
7.8Entertainment
7.2Food
8.5Crew
7.9Comfort
Airline reviews

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.

6.0 GoodLakshmi, Apr 2026
JFK - SFO
Read more Delta reviews

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.

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

It was good. The leg room was not great in Row 1.

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

Information on your arrival and departure airports