JFK - MDW

$98 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 8/19. 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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Flights 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, Sep 20 - Tue, Sep 23
Frontier Logo
1:01 pm - 11:09 pmJFK-MDW
11h 08m1 stop
Frontier Logo
8:00 am - 7:28 amMDW-JFK
22h 28m1 stop
$182Frontier
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Tue, Sep 9 - Wed, Sep 10
Frontier Logo
9:00 am - 10:58 pmJFK-MDW
14h 58m1 stop
Frontier Logo
8:00 am - 12:40 amMDW-JFK
15h 40m1 stop
$184Frontier
Find Deal
Tue, Sep 23 - Fri, Sep 26
Frontier Logo
9:00 am - 10:58 pmJFK-MDW
14h 58m1 stop
Frontier Logo
7:23 pm - 7:28 amMDW-JFK
11h 05m1 stop
$188Frontier
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Sat, Aug 23 - Wed, Aug 27
Frontier Logo
1:00 pm - 11:11 pmJFK-MDW
11h 11m1 stop
Frontier Logo
8:00 am - 7:29 amMDW-JFK
22h 29m1 stop
$193Frontier
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Sat, Aug 23 - Mon, Aug 25
Frontier Logo
1:00 pm - 11:11 pmJFK-MDW
11h 11m1 stop
Frontier Logo
11:03 am - 7:39 amMDW-JFK
19h 36m1 stop
$194Frontier
Find Deal
Thu, Sep 25 - Mon, Sep 29
Frontier Logo
1:01 pm - 6:18 pmJFK-MDW
6h 17m1 stop
Frontier Logo
7:23 pm - 11:59 amMDW-JFK
15h 36m1 stop
$203Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Frontier Logo
1:01 pm - 6:18 pmJFK-MDW
6h 17m1 stop
Frontier Logo
7:23 pm - 7:28 amMDW-JFK
11h 05m1 stop
$204Frontier
Find Deal
Sun, Aug 31 - Tue, Sep 2
Frontier Logo
6:00 am - 11:27 pmJFK-MDW
18h 27m1 stop
Frontier Logo
8:00 am - 12:27 amMDW-JFK
15h 27m1 stop
$205Frontier
Find Deal
Tue, Aug 12 - Thu, Aug 21
Delta Logo
7:45 pm - 8:35 amJFK-MDW
13h 50m1 stop
Delta Logo
9:31 am - 11:38 pmMDW-JFK
13h 07m1 stop
$253Delta
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Wed, Jul 9 - Sat, Jul 12
Delta Logo
1:00 pm - 6:40 pmJFK-MDW
6h 40m1 stop
Delta Logo
5:53 pm - 11:38 pmMDW-JFK
4h 45m1 stop
$294Delta
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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 October, where the average cost of round-trip tickets is $814 and $545 respectively.

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Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$98
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 124% 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 $98 for a one-way ticket and $182 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.

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.
8.0
DeltaOverall score based on 7950 reviews
7.3Food
7.9Comfort
7.9Entertainment
8.2Boarding
8.5Crew
Airline reviews

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

8.0 ExcellentTrisha, Jun 2025JFK - LAX
Read more Delta reviews

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

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

The WiFi has been awful on my last few Delta Air Lines flights.

Only one side of the heafphone jack work. Crew was friendly and helpful.

Typical flying experience in the US. Nothing particularly good or bad.

I was able to select a gluten free meal for my outbound flight operated by KLM but my selection wasn’t saved on Delta so I ended up not having a hot meal. The cabin crew was nice enough to offer some cheese so I could pair it with some gf crackers I had. The seat would recline but slowly but surely would come back up so I couldn’t sleep as I would have wanted to.

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)

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