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JFK - MDW

$87 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.
1 adult

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 Flight Deals 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.

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

KAYAK's recommended round-trip deals from the most popular airlines that fly from John F Kennedy Intl to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Frontier Logo
6:00 am - 11:26 amJFK-MDW
6h 26m1 stop
Frontier Logo
2:12 pm - 12:35 amMDW-JFK
9h 23m1 stop
$178Frontier
Find Deal
Wed, May 7 - Wed, May 7
Frontier Logo
6:59 am - 2:48 pmJFK-MDW
32h 49m1 stop
Frontier Logo
2:12 pm - 12:35 amMDW-JFK
9h 23m1 stop
$181Frontier
Find Deal
Sat, May 10 - Wed, May 14
Frontier Logo
6:59 am - 8:17 pmJFK-MDW
14h 18m1 stop
Frontier Logo
5:36 pm - 12:45 amMDW-JFK
6h 09m1 stop
$187Frontier
Find Deal
Fri, Jun 6 - Tue, Jun 10
Frontier Logo
9:00 am - 3:39 pmJFK-MDW
7h 39m1 stop
Frontier Logo
9:12 pm - 10:29 amMDW-JFK
12h 17m1 stop
$188Frontier
Find Deal
Tue, Jun 3 - Fri, Jun 6
Frontier Logo
6:59 am - 8:17 pmJFK-MDW
14h 18m1 stop
Frontier Logo
5:36 pm - 12:45 amMDW-JFK
6h 09m1 stop
$191Frontier
Find Deal
Fri, Jun 6 - Tue, Jun 10
Frontier Logo
6:59 am - 2:48 pmJFK-MDW
32h 49m1 stop
Frontier Logo
2:12 pm - 12:35 amMDW-JFK
9h 23m1 stop
$193Frontier
Find Deal
Sun, May 4 - Wed, May 7
Frontier Logo
11:10 am - 10:37 pmJFK-MDW
12h 27m1 stop
Frontier Logo
9:12 pm - 10:29 amMDW-JFK
12h 17m1 stop
$198Frontier
Find Deal
Thu, Jun 5 - Sun, Jun 8
Frontier Logo
6:59 am - 8:17 pmJFK-MDW
14h 18m1 stop
Frontier Logo
6:25 am - 5:30 amMDW-JFK
22h 05m1 stop
$201Frontier
Find Deal
Fri, May 30 - Mon, Jun 2
Delta Logo
7:15 am - 6:45 pmJFK-MDW
12h 30m1 stop
Delta Logo
9:24 am - 6:30 pmMDW-JFK
8h 06m1 stop
$203Delta
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Wed, Jun 4 - Tue, Jul 1
Delta Logo
8:05 am - 3:20 pmJFK-MDW
8h 15m1 stop
Delta Logo
9:24 am - 11:40 pmMDW-JFK
13h 16m1 stop
$247Delta
Find Deal
Sat, May 31 - Mon, Jun 30

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 January, where tickets cost $290 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $814 and $655 respectively.
Find deals

Good to know

Low season

September

High season

December

Cheapest flight

$87
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 85% 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 $87 for a one-way ticket and $178 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 7920 reviews
8.5Crew
7.3Food
8.2Boarding
7.9Entertainment
7.9Comfort
Airline reviews

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

2.0 MediocreAnonymous, Mar 2025JFK - ATL
Read more Delta reviews

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.

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.

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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