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$49 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 2/4. 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
0 bags

Search 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
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

Save 23% or moreCompare multiple travel sites with one search.

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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
3:00 pm - 10:02 amJFK-MDW
20h 02m1 stop
11:33 am - 1:59 pmMDW-JFK
25h 26m1 stop
$99Frontier
Find Deal
Sat, Feb 8 - Mon, Feb 10
3:00 pm - 10:02 amJFK-MDW
20h 02m1 stop
11:33 am - 1:59 pmMDW-JFK
25h 26m1 stop
$100Frontier
Find Deal
Sat, Jan 25 - Mon, Jan 27
11:00 am - 4:16 pmJFK-MDW
6h 16m1 stop
4:20 pm - 10:15 amMDW-JFK
16h 55m1 stop
$101Frontier
Find Deal
Tue, Feb 4 - Wed, Feb 12
11:00 am - 4:16 pmJFK-MDW
6h 16m1 stop
4:20 pm - 10:15 amMDW-JFK
16h 55m1 stop
$102Frontier
Find Deal
Tue, Feb 4 - Wed, Feb 12
11:04 am - 3:21 pmJFK-MDW
29h 17m1 stop
7:15 am - 10:05 amMDW-JFK
25h 50m1 stop
$104Frontier
Find Deal
Sat, Jan 25 - Mon, Jan 27
3:00 pm - 10:02 amJFK-MDW
20h 02m1 stop
7:15 am - 10:05 amMDW-JFK
25h 50m1 stop
$105Frontier
Find Deal
Sat, Jan 25 - Mon, Jan 27
3:00 pm - 10:02 amJFK-MDW
20h 02m1 stop
11:33 am - 1:59 pmMDW-JFK
25h 26m1 stop
$106Frontier
Find Deal
Sat, Jan 25 - Mon, Jan 27
3:00 pm - 10:02 amJFK-MDW
20h 02m1 stop
7:15 am - 10:05 amMDW-JFK
25h 50m1 stop
$107Frontier
Find Deal
Sat, Jan 25 - Mon, Jan 27
6:00 am - 10:12 amJFK-MDW
5h 12m1 stop
6:28 pm - 11:14 pmMDW-JFK
3h 46m1 stop
$294Delta
Find Deal
Sat, Jan 11 - Sun, Jan 12
8:55 am - 2:53 pmJFK-MDW
6h 58m1 stop
3:41 pm - 12:46 amMDW-JFK
8h 05m1 stop
$296Delta
Find Deal
Sat, Jan 11 - Sat, Jan 25

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 Monday 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 $188 (return) on average. On the other hand, the most expensive months are May and July, where the average cost of round-trip tickets is $517 and $414 respectively.

Good to know

Low season

February

High season

December

Cheapest flight

$49
Best time to beat the crowds with an average 9% drop 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 $49 for a one-way ticket and $99 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 8580 reviews
8.6Crew
7.3Food
8.2Boarding
8.0Comfort
7.9Entertainment
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 +

Book cheap flights from New York to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from New York to Chicago found on KAYAK in the last 72 hours.
2/4Tue
1 stopFrontier
6h 16mJFK-MDW
$49
1/28Tue
1 stopFrontier
6h 16mJFK-MDW
$50
2/4Tue
1 stopFrontier
6h 16mJFK-MDW
$51
1/14Tue
1 stopFrontier
6h 14mJFK-MDW
$52
1/15Wed
1 stopFrontier
7h 57mJFK-MDW
$53
1/10Fri
1 stopDelta
5h 12mJFK-MDW
$148
1/4Sat
1 stopDelta
5h 39mJFK-MDW
$150
1/18Sat
1 stopDelta
7h 18mJFK-MDW
$158
3/1Sat
1 stopDelta
9h 53mJFK-MDW
$167
1/9Thu
1 stopSun Country Air
7h 19mJFK-MDW
$202

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Last minute flights from John F Kennedy Intl to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from New York to Chicago that are departing in the next 10 days.
12/30Mon
multi-stopFrontier
27h 54mJFK-MDW
1/19Sun
multi-stopFrontier
24h 20mMDW-JFK
$320
12/28Sat
multi-stopDelta
5h 39mJFK-MDW
1/5Sun
multi-stopDelta
3h 49mMDW-JFK
$378
12/28Sat
multi-stopDelta
4h 29mJFK-MDW
1/15Wed
multi-stopDelta
6h 24mMDW-JFK
$410
12/28Sat
multi-stopDelta
4h 29mJFK-MDW
1/3Fri
multi-stopDelta
5h 45mMDW-JFK
$413
12/28Sat
multi-stopDelta
5h 39mJFK-MDW
1/3Fri
multi-stopDelta
5h 45mMDW-JFK
$431
12/28Sat
multi-stopDelta
5h 39mJFK-MDW
1/2Thu
multi-stopDelta
5h 45mMDW-JFK
$446
12/28Sat
multi-stopDelta
5h 39mJFK-MDW
1/4Sat
multi-stopDelta
5h 45mMDW-JFK
$456
12/30Mon
multi-stopFrontier
27h 54mJFK-MDW
1/2Thu
multi-stopFrontier
14h 11mMDW-JFK
$464
12/27Fri
multi-stopDelta
6h 21mJFK-MDW
1/3Fri
multi-stopDelta
5h 45mMDW-JFK
$473
12/26Thu
multi-stopDelta
6h 44mJFK-MDW
1/2Thu
multi-stopDelta
5h 45mMDW-JFK
$474

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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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