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Cheap flights from New York John F Kennedy Intl Airport to Chicago from $63

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 departing on 3/3. 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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0 bags

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Find the cheapest flights from New York John F Kennedy Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
1:00 pm - 9:33 pm
JFK
-
MDW
9h 33m
1 stop
Frontier Logo
8:00 am - 3:29 pm
MDW
-
JFK
6h 29m
1 stop
$128Frontier
Sat, Feb 21 - Sat, Feb 28
Frontier Logo
1:00 pm - 9:39 pm
JFK
-
MDW
9h 39m
1 stop
Frontier Logo
2:19 pm - 1:03 am
MDW
-
JFK
9h 44m
1 stop
$138Frontier
Sat, Feb 28 - Mon, Mar 2
Frontier Logo
1:00 pm - 7:07 pm
JFK
-
MDW
7h 07m
1 stop
Frontier Logo
11:19 am - 12:16 pm
MDW
-
JFK
23h 57m
1 stop
$144Frontier
Tue, Mar 3 - Tue, Mar 10
Frontier Logo
6:00 am - 4:16 pm
JFK
-
MDW
11h 16m
1 stop
Frontier Logo
2:19 pm - 1:03 am
MDW
-
JFK
9h 44m
1 stop
$148Frontier
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
11:03 am - 2:26 pm
JFK
-
MDW
28h 23m
1 stop
Frontier Logo
8:00 am - 3:29 pm
MDW
-
JFK
6h 29m
1 stop
$149Frontier
Thu, Feb 26 - Sat, Feb 28
Frontier Logo
1:00 pm - 6:38 pm
JFK
-
MDW
6h 38m
1 stop
Frontier Logo
9:04 pm - 1:03 am
MDW
-
JFK
26h 59m
1 stop
$152Frontier
Fri, Feb 27 - Sun, Mar 1
Frontier Logo
10:00 am - 7:47 pm
JFK
-
MDW
10h 47m
1 stop
Frontier Logo
2:41 pm - 9:03 am
MDW
-
JFK
17h 22m
1 stop
$153Frontier
Fri, Mar 6 - Sun, Mar 8
Frontier Logo
1:00 pm - 9:33 pm
JFK
-
MDW
9h 33m
1 stop
Frontier Logo
2:19 pm - 1:03 am
MDW
-
JFK
9h 44m
1 stop
$154Frontier
Sat, Feb 21 - Mon, Feb 23
Frontier Logo
11:30 am - 10:19 pm
JFK
-
MDW
11h 49m
1 stop
Frontier Logo
2:20 pm - 12:59 am
MDW
-
JFK
9h 39m
1 stop
$159Frontier
Mon, Apr 20 - Wed, Apr 22
Frontier Logo
1:00 pm - 7:07 pm
JFK
-
MDW
7h 07m
1 stop
Frontier Logo
12:22 pm - 1:03 am
MDW
-
JFK
11h 41m
1 stop
$160Frontier
Wed, Feb 18 - Thu, Feb 19

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
Mar 5
JFK7:00 amNew York John F Kennedy Intl
6h 46m
1 stop
MDW12:46 pmChicago Midway
Mar 7
MDW6:00 amChicago Midway
5h 31m
1 stop
JFK12:31 pmNew York John F Kennedy Intl
$227
Delta
Feb 7
JFK7:05 amNew York John F Kennedy Intl
6h 41m
1 stop
MDW12:46 pmChicago Midway
Feb 7
MDW5:00 pmChicago Midway
5h 45m
1 stop
JFK11:45 pmNew York John F Kennedy Intl
$265
Delta
Feb 14
JFK6:29 amNew York John F Kennedy Intl
7h 17m
1 stop
MDW12:46 pmChicago Midway
Mar 7
MDW6:00 amChicago Midway
5h 31m
1 stop
JFK12:31 pmNew York John F Kennedy Intl
$281

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 21
JFK1:00 pmNew York John F Kennedy Intl
9h 33m
1 stop
MDW9:33 pmChicago Midway
Feb 28
MDW8:00 amChicago Midway
6h 29m
1 stop
JFK3:29 pmNew York John F Kennedy Intl
$128
Frontier
Feb 28
JFK1:00 pmNew York John F Kennedy Intl
9h 39m
1 stop
MDW9:39 pmChicago Midway
Mar 2
MDW2:19 pmChicago Midway
9h 44m
1 stop
JFK1:03 amNew York John F Kennedy Intl
$137
Frontier
Feb 28
JFK1:00 pmNew York John F Kennedy Intl
9h 39m
1 stop
MDW9:39 pmChicago Midway
Mar 2
MDW2:19 pmChicago Midway
9h 44m
1 stop
JFK1:03 amNew York John F Kennedy Intl
$138

momondo Fare Finder

 
Customize your flight search to find flights from New York John F Kennedy Intl Airport to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 2, 2026.
Use the filters below to find and compare flights from New York John F Kennedy Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 2/21

1:00 pm-9:33 pm

1 stop9h 33m

Chicago Midway

Sat 2/28

8:00 am-3:29 pm

1 stop6h 29m

$128

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 2/28

1:00 pm-9:39 pm

1 stop9h 39m

Chicago Midway

Mon 3/2

2:19 pm-1:03 am

1 stop9h 44m

$138

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 3/3

1:00 pm-7:07 pm

1 stop7h 07m

Chicago Midway

Tue 3/10

11:19 am-12:16 pm

1 stop23h 57m

$144

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 2/26

6:00 am-4:16 pm

1 stop11h 16m

Chicago Midway

Mon 3/2

2:19 pm-1:03 am

1 stop9h 44m

$148

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 2/26

11:03 am-2:26 pm

1 stop28h 23m

Chicago Midway

Sat 2/28

8:00 am-3:29 pm

1 stop6h 29m

$149

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 2/27

1:00 pm-6:38 pm

1 stop6h 38m

Chicago Midway

Sun 3/1

9:04 pm-1:03 am

1 stop26h 59m

$152

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 3/6

10:00 am-7:47 pm

1 stop10h 47m

Chicago Midway

Sun 3/8

2:41 pm-9:03 am

1 stop17h 22m

$153

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 2/21

1:00 pm-9:33 pm

1 stop9h 33m

Chicago Midway

Mon 2/23

2:19 pm-1:03 am

1 stop9h 44m

$154

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 4/20

11:30 am-10:19 pm

1 stop11h 49m

Chicago Midway

Wed 4/22

2:20 pm-12:59 am

1 stop9h 39m

$159

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 2/18

1:00 pm-7:07 pm

1 stop7h 07m

Chicago Midway

Thu 2/19

12:22 pm-1:03 am

1 stop11h 41m

$160

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 May 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 $92. If you are unable to visit Chicago Midway Airport during the month of May, then departing from New York John F Kennedy Intl Airport during the month December is also very affordable. Most momondo users find prices during this month for around $139.

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 $256. 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, Monday 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 $396.

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 $221 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $354. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

Fastest flight time

5h 57m

Direct flights

None
The fastest flight from New York John F Kennedy Intl Airport to Chicago Midway Airport takes 5h 57m
There are no direct flights from New York John F Kennedy Intl Airport to Chicago Midway Airport. There are no popular flight routes from New York John F Kennedy Intl Airport to Chicago Midway Airport.
Search flight deals

  • 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 5h 57m, 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 $296Free CancellationRating
7.9
8,132 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

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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