JFK - MDW

$63 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 2/25. 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
$128
Overall average: $301
Frontier
Sat 2/21Sat 2/28
JFK - MDW • 1 stop
Cheapest one-way
$63
Typical prices: $148-$228
Frontier
Wed 2/25
JFK - MDW • 1 stop
Top airlines
Frontier
Cheapest • from $128 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
May
Cheapest • 73% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, Feb 21 - Sat, Feb 28
Frontier Logo
1:00 pm - 9:33 pm
JFK
-
MDW
9h 33m
1 stop
Frontier Logo
8:00 am - 3:29 pm
MDW
-
JFK
6h 29m
1 stop
$128Frontier
Sat, Feb 28 - Mon, Mar 2
Frontier Logo
1:00 pm - 9:39 pm
JFK
-
MDW
9h 39m
1 stop
Frontier Logo
2:19 pm - 1:03 am
MDW
-
JFK
9h 44m
1 stop
$138Frontier
Sat, Feb 21 - Sat, Feb 28
Frontier Logo
1:00 pm - 9:33 pm
JFK
-
MDW
9h 33m
1 stop
Frontier Logo
8:00 am - 3:29 pm
MDW
-
JFK
6h 29m
1 stop
$140Frontier
Tue, Mar 3 - Tue, Mar 10
Frontier Logo
1:00 pm - 7:07 pm
JFK
-
MDW
7h 07m
1 stop
Frontier Logo
11:19 am - 12:16 pm
MDW
-
JFK
23h 57m
1 stop
$144Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
6:00 am - 11:27 am
JFK
-
MDW
6h 27m
1 stop
Frontier Logo
2:19 pm - 1:03 am
MDW
-
JFK
9h 44m
1 stop
$148Frontier
Thu, Feb 26 - Sat, Feb 28
Frontier Logo
11:03 am - 2:26 pm
JFK
-
MDW
28h 23m
1 stop
Frontier Logo
8:00 am - 3:29 pm
MDW
-
JFK
6h 29m
1 stop
$149Frontier
Sat, Feb 28 - Sun, Mar 1
Frontier Logo
1:00 pm - 9:39 pm
JFK
-
MDW
9h 39m
1 stop
Frontier Logo
9:04 pm - 1:03 am
MDW
-
JFK
26h 59m
1 stop
$151Frontier
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
6:00 am - 11:27 am
JFK
-
MDW
6h 27m
1 stop
Frontier Logo
5:16 pm - 1:03 am
MDW
-
JFK
6h 47m
1 stop
$152Frontier
Wed, Feb 18 - Mon, Feb 23
Frontier Logo
10:02 am - 1:56 pm
JFK
-
MDW
28h 54m
1 stop
Frontier Logo
2:19 pm - 1:03 am
MDW
-
JFK
9h 44m
1 stop
$154Frontier
Tue, Feb 17 - Wed, Feb 18
Frontier Logo
6:00 am - 7:07 pm
JFK
-
MDW
14h 07m
1 stop
Frontier Logo
7:00 am - 1:03 am
MDW
-
JFK
17h 03m
1 stop
$156Frontier
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.

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 May, where tickets cost $92 (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.

Find deals

Good to know

Low seasonAugust
Cheapest flight$63
Best time to beat the crowds but there is an average 78% increase in price.
Most popular time to fly with an average 11% 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 $63 for a one-way ticket and $128 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 8128 reviews
7.9Comfort
8.1Boarding
7.2Food
8.5Crew
7.8Entertainment
Airline reviews

The flight was comfortable and uneventful, which is what I desire

8.0 ExcellentLarry, Jan 2026
JFK - SJD
Read more Delta reviews

The flight was comfortable and uneventful, which is what I desire

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

I truly love flying with Delta. They have always treated me with the upmost respect

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight was great. The gate location was way to far away!!!

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

I believe that a four-hour trip should have a meal. Delta had none.

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)