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Cheap flights from New York John F Kennedy Intl Airport to Chicago Midway Airport from $50

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport departing on 1/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from New York John F Kennedy Intl Airport to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from New York John F Kennedy Intl Airport to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from New York John F Kennedy Intl Airport to Chicago.

Cheap last minute flights

Planning a quick getaway from New York John F Kennedy Intl Airport to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from New York John F Kennedy Intl Airport to Chicago

Find recent round-trip train or bus tickets from New York John F Kennedy Intl Airport to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:04 am - 3:21 pmJFK-MDW
29h 17m1 stop
7:15 am - 10:05 amMDW-JFK
25h 50m1 stop
$96Frontier
Find Deal
Sat, Feb 8 - Mon, Feb 10
11:00 am - 7:06 pmJFK-MDW
9h 06m1 stop
4:20 pm - 10:15 amMDW-JFK
16h 55m1 stop
$99Frontier
Find Deal
Wed, Feb 5 - Wed, Feb 12
11:04 am - 3:21 pmJFK-MDW
29h 17m1 stop
11:33 am - 1:59 pmMDW-JFK
25h 26m1 stop
$100Frontier
Find Deal
Sat, Feb 8 - Mon, Feb 10
11:00 am - 7:06 pmJFK-MDW
9h 06m1 stop
12:43 pm - 6:30 amMDW-JFK
16h 47m1 stop
$104Frontier
Find Deal
Wed, Feb 5 - Thu, Feb 6
11:00 am - 6:37 pmJFK-MDW
8h 37m1 stop
7:15 am - 10:03 amMDW-JFK
25h 48m1 stop
$105Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
11:00 am - 6:37 pmJFK-MDW
8h 37m1 stop
7:15 am - 10:03 amMDW-JFK
25h 48m1 stop
$106Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
11:00 am - 6:37 pmJFK-MDW
8h 37m1 stop
7:15 am - 10:03 amMDW-JFK
25h 48m1 stop
$107Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
11:00 am - 6:37 pmJFK-MDW
8h 37m1 stop
7:15 am - 10:03 amMDW-JFK
25h 48m1 stop
$108Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
7:05 am - 1:08 pmJFK-MDW
7h 03m1 stop
5:07 pm - 12:47 amMDW-JFK
6h 40m1 stop
$296Delta
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Tue, Jan 7 - Tue, Jan 21
6:29 am - 11:08 amJFK-MDW
5h 39m1 stop
6:28 pm - 11:14 pmMDW-JFK
3h 46m1 stop
$298Delta
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Sat, Jan 4 - Mon, Jan 6
11:00 am - 4:16 pmJFK-MDW
6h 16m1 stop
$50Frontier
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Tue, Jan 28
11:00 am - 4:16 pmJFK-MDW
6h 16m1 stop
$51Frontier
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Tue, Feb 11
11:00 am - 4:14 pmJFK-MDW
6h 14m1 stop
$52Frontier
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Tue, Jan 14
11:00 am - 6:37 pmJFK-MDW
8h 37m1 stop
$54Frontier
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Thu, Jan 9
11:00 am - 6:37 pmJFK-MDW
8h 37m1 stop
$55Frontier
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Thu, Jan 9
11:15 am - 10:51 pmJFK-MDW
12h 36m1 stop
$56Frontier
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Sat, Feb 22
11:01 am - 4:55 pmJFK-MDW
6h 54m1 stop
$57Frontier
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Wed, Mar 19
11:00 am - 6:26 pmJFK-MDW
8h 26m1 stop
$60Frontier
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Thu, Jan 23
7:05 am - 1:08 pmJFK-MDW
7h 03m1 stop
$148Delta
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Tue, Jan 7
6:29 am - 11:08 amJFK-MDW
5h 39m1 stop
$150Delta
Find Deal
Sat, Jan 4
12:55 pm - 4:10 pmJFK-MDW
4h 15m1 stop
5:04 pm - 11:49 pmMDW-JFK
5h 45m1 stop
$378Delta
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Wed, Dec 25 - Fri, Jan 3
12:00 pm - 5:11 pmJFK-MDW
6h 11m1 stop
6:28 pm - 11:14 pmMDW-JFK
3h 46m1 stop
$429Delta
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Tue, Dec 24 - Wed, Jan 15
3:59 pm - 10:06 pmJFK-MDW
7h 07m1 stop
5:04 pm - 11:49 pmMDW-JFK
5h 45m1 stop
$446Delta
Find Deal
Wed, Dec 25 - Thu, Jan 2
3:59 pm - 10:06 pmJFK-MDW
7h 07m1 stop
5:04 pm - 11:49 pmMDW-JFK
5h 45m1 stop
$473Delta
Find Deal
Fri, Dec 27 - Fri, Jan 3
12:00 pm - 5:11 pmJFK-MDW
6h 11m1 stop
5:04 pm - 11:49 pmMDW-JFK
5h 45m1 stop
$489Delta
Find Deal
Tue, Dec 24 - Sat, Jan 4
12:00 pm - 5:11 pmJFK-MDW
6h 11m1 stop
3:32 pm - 11:54 pmMDW-JFK
7h 22m1 stop
$492Delta
Find Deal
Tue, Dec 24 - Wed, Dec 25
11:00 am - 4:57 pmJFK-MDW
6h 57m1 stop
4:08 pm - 9:03 amMDW-JFK
15h 55m1 stop
$508Frontier
Find Deal
Thu, Dec 26 - Tue, Dec 31
6:00 am - 11:21 amJFK-MDW
6h 21m1 stop
5:04 pm - 11:49 pmMDW-JFK
5h 45m1 stop
$513Delta
Find Deal
Fri, Dec 27 - Fri, Jan 3
3:59 pm - 10:06 pmJFK-MDW
7h 07m1 stop
9:30 am - 8:12 pmMDW-JFK
9h 42m1 stop
$516Delta
Find Deal
Wed, Dec 25 - Tue, Dec 31
11:00 am - 4:57 pmJFK-MDW
6h 57m1 stop
4:08 pm - 9:03 amMDW-JFK
15h 55m1 stop
$570Frontier
Find Deal
Thu, Dec 26 - Tue, Dec 31

Frontier flights from New York John F Kennedy Intl Airport to Chicago Midway Airport

Our best Frontier deals on New York John F Kennedy Intl Airport to Chicago Midway Airport flight tickets
Frontier
Feb 8
JFK11:04 amNew York John F Kennedy Intl
29h 17m
1 stop
MDW3:21 pmChicago Midway
Feb 10
MDW7:15 amChicago Midway
25h 50m
1 stop
JFK10:05 amNew York John F Kennedy Intl
Frontier
Feb 5
JFK11:00 amNew York John F Kennedy Intl
9h 06m
1 stop
MDW7:06 pmChicago Midway
Feb 12
MDW4:20 pmChicago Midway
16h 55m
1 stop
JFK10:15 amNew York John F Kennedy Intl
Frontier
Feb 8
JFK11:04 amNew York John F Kennedy Intl
29h 17m
1 stop
MDW3:21 pmChicago Midway
Feb 10
MDW11:33 amChicago Midway
25h 26m
1 stop
JFK1:59 pmNew York John F Kennedy Intl

Delta flights from New York John F Kennedy Intl Airport to Chicago Midway Airport

Our best Delta deals on New York John F Kennedy Intl Airport to Chicago Midway Airport flight tickets
Delta
Jan 7
JFK7:05 amNew York John F Kennedy Intl
7h 03m
1 stop
MDW1:08 pmChicago Midway
Jan 21
MDW5:07 pmChicago Midway
6h 40m
1 stop
JFK12:47 amNew York John F Kennedy Intl
Delta
Jan 4
JFK6:29 amNew York John F Kennedy Intl
5h 39m
1 stop
MDW11:08 amChicago Midway
Jan 6
MDW6:28 pmChicago Midway
3h 46m
1 stop
JFK11:14 pmNew York John F Kennedy Intl
Delta
Dec 31
JFK12:00 pmNew York John F Kennedy Intl
6h 11m
1 stop
MDW5:11 pmChicago Midway
Jan 3
MDW5:04 pmChicago Midway
5h 45m
1 stop
JFK11:49 pmNew York John F Kennedy Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from New York John F Kennedy Intl Airport to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from New York John F Kennedy Intl Airport, with most prices found around $188. If you are unable to visit Chicago Midway Airport during the month of January, then departing from New York John F Kennedy Intl Airport during the month June is also very affordable. Most momondo users find prices during this month for around $208.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from New York John F Kennedy Intl Airport. The lowest ticket price found for a Tuesday departure recently was $228. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from New York John F Kennedy Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $454.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from New York John F Kennedy Intl Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $228 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $294. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on New York John F Kennedy Intl Airport to Chicago Midway Airport flights?

You could potentially save up to 60% on your flight if you consider stops on a New York John F Kennedy Intl Airport to Chicago Midway Airport flight.

How have New York John F Kennedy Intl Airport to Chicago Midway Airport flight prices changed over time?

As of December 2024, prices for New York John F Kennedy Intl Airport to Chicago Midway Airport flights are approximately 48% cheaper when compared to flights at the same time last year.

When to book flights from New York John F Kennedy Intl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from New York John F Kennedy Intl Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap New York John F Kennedy Intl Airport to Chicago Midway Airport (JFK to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New York John F Kennedy Intl Airport to Chicago Midway Airport

Best Price Found

$50

Fastest flight time

4h 01m

Direct flights

None
The best one-way flight to Chicago Midway Airport from New York John F Kennedy Intl Airport in the past 72 hours is $50. The best round-trip flight deal from New York John F Kennedy Intl Airport to Chicago Midway Airport found on momondo in the last 72 hours is $96.
The fastest flight from New York John F Kennedy Intl Airport to Chicago Midway Airport takes 4h 01m
There are no direct flights from New York John F Kennedy Intl Airport to Chicago Midway Airport. Popular non-direct route for this connection is New York John F Kennedy Intl Airport - Chicago Midway Airport.

  • How far is New York John F Kennedy Intl to Chicago Midway by plane?

    Chicago Midway is 728.9 mi away from New York John F Kennedy Intl. Flights usually cover this in 4h 01m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from New York John F Kennedy Intl Airport to Chicago Midway Airport?

    Prices for flights from New York John F Kennedy Intl Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from New York John F Kennedy Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from New York John F Kennedy Intl Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from New York John F Kennedy Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from New York John F Kennedy Intl Airport to Chicago Midway Airport?


Best airlines flying from New York John F Kennedy Intl Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from New York John F Kennedy Intl Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $294Free CancellationRating
8.0
8,594 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from New York to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from New York to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from New York to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from New York on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from New York to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from New York to Chicago.

I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for New York to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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