JFK - MDW

$82 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 10/23. 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

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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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, Oct 28 - Wed, Nov 5
Frontier Logo
6:25 am - 11:38 amJFK-MDW
6h 13m1 stop
Frontier Logo
2:06 pm - 12:33 amMDW-JFK
9h 27m1 stop
$146Frontier
Find Deal
Fri, Nov 14 - Sat, Nov 15
Frontier Logo
10:00 am - 6:39 pmJFK-MDW
9h 39m1 stop
Frontier Logo
1:37 pm - 12:33 amMDW-JFK
9h 56m1 stop
$147Frontier
Find Deal
Sat, Nov 1 - Mon, Nov 3
Frontier Logo
9:00 am - 6:39 pmJFK-MDW
10h 39m1 stop
Frontier Logo
1:37 pm - 12:33 amMDW-JFK
9h 56m1 stop
$148Frontier
Find Deal
Sat, Nov 8 - Sun, Nov 9
Frontier Logo
10:00 am - 6:39 pmJFK-MDW
9h 39m1 stop
Frontier Logo
10:12 am - 10:29 amMDW-JFK
23h 17m1 stop
$149Frontier
Find Deal
Sat, Nov 1 - Sun, Nov 2
Frontier Logo
9:00 am - 6:39 pmJFK-MDW
10h 39m1 stop
Frontier Logo
10:12 am - 10:29 amMDW-JFK
23h 17m1 stop
$156Frontier
Find Deal
Sat, Nov 1 - Sun, Nov 2
Frontier Logo
9:00 am - 6:39 pmJFK-MDW
10h 39m1 stop
Frontier Logo
10:12 am - 10:29 amMDW-JFK
23h 17m1 stop
$157Frontier
Find Deal
Tue, Oct 21 - Thu, Oct 23
Frontier Logo
9:00 am - 1:38 pmJFK-MDW
5h 38m1 stop
Frontier Logo
9:26 pm - 7:28 amMDW-JFK
9h 02m1 stop
$158Frontier
Find Deal
Mon, Sep 22 - Tue, Sep 23
Frontier Logo
6:15 am - 4:00 pmJFK-MDW
10h 45m1 stop
Frontier Logo
2:32 pm - 1:08 amMDW-JFK
9h 36m1 stop
$164Frontier
Find Deal
Fri, Sep 26 - Sat, Sep 27
Frontier Logo
12:59 pm - 8:52 pmJFK-MDW
8h 53m1 stop
Frontier Logo
10:51 am - 10:26 amMDW-JFK
22h 35m1 stop
$165Frontier
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
6:15 am - 4:00 pmJFK-MDW
10h 45m1 stop
Frontier Logo
6:21 am - 10:01 amMDW-JFK
26h 40m1 stop
$166Frontier
Find Deal

Everything you should know

When to travel
May
Cheapest • 76% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$146
Overall average: $545
Frontier
Tue 10/28Wed 11/5
JFK - MDW • 1 stop
Cheapest one-way
$82
Typical prices: $150-277
Frontier
Thu 10/23
JFK - MDW • 1 stop
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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!
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’s the cheapest day of the week to fly from New York John F Kennedy Airport to Chicago Midway Airport?

The average price of all round-trip flights from New York John F Kennedy Intl Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

When flying from New York John F Kennedy Airport to Chicago Midway Airport, you should consider leaving on a Tuesday and avoid Sundays if you are looking for the best rates. For your return to New York John F Kennedy Airport, you’ll find the best rates on Saturdays and the most expensive ones on Thursdays.

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 December and August, where the average cost of round-trip tickets is $814 and $611 respectively.

Good to know

Low seasonAugust
Cheapest flight$82
Best time to beat the crowds but there is an average 57% increase in price.
Most popular time to fly with an average 109% 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 $82 for a one-way ticket and $146 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.

  • 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 7954 reviews
7.9Comfort
8.5Crew
7.9Entertainment
8.2Boarding
7.3Food
Airline reviews

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

8.0 ExcellentPolycarp, Aug 2025JFK - SLC
Read more Delta reviews

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

Was charged for my luggage despite having been on one ticket from an international flight. Too tired to argue after 15 hours on flight. Was charged for rechecking it at JFK airport. Not sure why those off Kenya Airways were required to do that.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

Overall, aside from the baggage issue, it was as good as one expects.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

Our bag was lost so that made unnecessary chaos On our trip

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

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