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JFK - MDW

$50 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 5/14. 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.
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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 Flight Deals from New York John F Kennedy Airport to Chicago Midway Airport (JFK-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New York John F Kennedy Airport to Chicago Midway Airport 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.

Recent round-trip flight deals from John F Kennedy Intl to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from John F Kennedy Intl to Midway.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:15 am - 11:00 pmJFK-MDW
12h 45m1 stop
4:20 pm - 10:15 amMDW-JFK
16h 55m1 stop
$98Frontier
Find Deal
Wed, Mar 5 - Mon, Mar 10
9:00 am - 5:18 pmJFK-MDW
9h 18m1 stop
6:43 pm - 7:29 amMDW-JFK
11h 46m1 stop
$100Frontier
Find Deal
Wed, May 7 - Sat, May 10
1:00 pm - 9:33 pmJFK-MDW
9h 33m1 stop
1:31 pm - 12:43 amMDW-JFK
10h 12m1 stop
$105Frontier
Find Deal
Wed, Apr 9 - Mon, Apr 14
1:00 pm - 9:33 pmJFK-MDW
9h 33m1 stop
5:15 am - 10:00 amMDW-JFK
27h 45m1 stop
$107Frontier
Find Deal
Wed, Apr 9 - Thu, Apr 10
11:15 am - 10:51 pmJFK-MDW
12h 36m1 stop
8:30 am - 12:02 pmMDW-JFK
26h 32m1 stop
$108Frontier
Find Deal
Sat, Mar 1 - Tue, Mar 4
11:15 am - 11:00 pmJFK-MDW
12h 45m1 stop
4:19 pm - 10:15 amMDW-JFK
16h 56m1 stop
$109Frontier
Find Deal
Wed, Feb 26 - Sat, Mar 1
11:15 am - 10:51 pmJFK-MDW
12h 36m1 stop
8:30 am - 12:02 pmMDW-JFK
26h 32m1 stop
$110Frontier
Find Deal
Sat, Feb 22 - Tue, Feb 25
1:02 pm - 7:29 pmJFK-MDW
7h 27m1 stop
2:41 pm - 10:15 amMDW-JFK
18h 34m1 stop
$111Frontier
Find Deal
Thu, Feb 20 - Mon, Feb 24
7:05 am - 1:05 pmJFK-MDW
7h 00m1 stop
5:05 pm - 12:42 amMDW-JFK
6h 37m1 stop
$291Delta
Find Deal
Tue, Feb 18 - Tue, Feb 18
12:59 pm - 6:11 pmJFK-MDW
6h 12m1 stop
5:05 pm - 12:42 amMDW-JFK
6h 37m1 stop
$297Delta
Find Deal
Tue, Feb 25 - Fri, Feb 28

Flights from John F Kennedy Intl to Midway - Travel Insights & Trends

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 January, where tickets cost $290 (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.

Good to know

Low season

May

High season

December

Cheapest flight

$50
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly with an average 81% 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 $50 for a one-way ticket and $98 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.

See more FAQs

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 8456 reviews
7.9Entertainment
8.0Comfort
8.5Crew
7.3Food
8.2Boarding
Airline reviews

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?

10.0 ExcellentFreddy, Dec 2024JFK - MKE
Read more Delta reviews

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.

Forced to check my bag which fit in carry on, boarded and then sat for over an hour waiting to take off with no explanation.

7 hour delay for mechanical reasons Handled badly by crew and delta personnel

Food was not the best. Too many items had sauce pm them with a lot of spices The seat was not comfortable especially when you lay down

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

Flight was canceled so it was not a great experience. Boarded, then deboarded. Delayed, boarded a new plane then deboarded the 2nd plane and flight was canceled. Then booked a fight to Rome and took a train to Venice the next day. Lost an entire day +

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

Information on your arrival and departure airports

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

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