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Cheap flights from New York John F Kennedy Intl Airport to Chicago from $98

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 9/3. 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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Find the cheapest flights from New York John F Kennedy Intl Airport to Chicago

Cheap round-trip flights

Frontier Logo
6:15 am - 11:09 pmJFK-MDW
17h 54m1 stop
Frontier Logo
8:00 am - 12:40 amMDW-JFK
15h 40m1 stop
$206Frontier
Find Deal
Sat, Nov 1 - Wed, Nov 5
Frontier Logo
9:00 am - 2:01 pmJFK-MDW
6h 01m1 stop
Frontier Logo
3:03 pm - 1:13 amMDW-JFK
9h 10m1 stop
$218Frontier
Find Deal
Wed, Aug 27 - Wed, Sep 3
Frontier Logo
6:15 am - 3:58 pmJFK-MDW
10h 43m1 stop
Frontier Logo
2:32 pm - 1:08 amMDW-JFK
9h 36m1 stop
$219Frontier
Find Deal
Wed, Sep 24 - Tue, Sep 30
Frontier Logo
1:00 pm - 8:36 pmJFK-MDW
8h 36m1 stop
Frontier Logo
6:30 am - 3:27 pmMDW-JFK
7h 57m1 stop
$225Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
1:01 pm - 11:17 pmJFK-MDW
11h 16m1 stop
Frontier Logo
6:21 am - 10:00 amMDW-JFK
26h 39m1 stop
$227Frontier
Find Deal
Sat, Sep 6 - Sun, Sep 7
Frontier Logo
11:00 am - 12:44 pmJFK-MDW
26h 44m1 stop
Frontier Logo
2:32 pm - 1:08 amMDW-JFK
9h 36m1 stop
$228Frontier
Find Deal
Sat, Sep 13 - Tue, Sep 16
Frontier Logo
9:00 am - 4:00 pmJFK-MDW
8h 00m1 stop
Frontier Logo
2:32 pm - 1:08 amMDW-JFK
9h 36m1 stop
$229Frontier
Find Deal
Fri, Sep 5 - Tue, Sep 9
Frontier Logo
6:59 am - 8:22 amJFK-MDW
26h 23m1 stop
Frontier Logo
6:20 am - 1:08 amMDW-JFK
17h 48m1 stop
$230Frontier
Find Deal
Thu, Aug 28 - Thu, Sep 4
Delta Logo
9:35 pm - 8:35 amJFK-MDW
12h 00m1 stop
Delta Logo
1:08 pm - 11:38 pmMDW-JFK
9h 30m1 stop
$252Delta
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Sat, Aug 23 - Wed, Aug 27
Delta Logo
7:45 pm - 6:37 pmJFK-MDW
23h 52m1 stop
Delta Logo
1:08 pm - 11:38 pmMDW-JFK
9h 30m1 stop
$262Delta
Find Deal
Tue, Aug 19 - Tue, Aug 26

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
Aug 23
JFK9:35 pmNew York John F Kennedy Intl
12h 00m
1 stop
MDW8:35 amChicago Midway
Aug 27
MDW1:08 pmChicago Midway
9h 30m
1 stop
JFK11:38 pmNew York John F Kennedy Intl
$252
Find similar
Delta
Aug 19
JFK7:45 pmNew York John F Kennedy Intl
23h 52m
1 stop
MDW6:37 pmChicago Midway
Aug 26
MDW1:08 pmChicago Midway
9h 30m
1 stop
JFK11:38 pmNew York John F Kennedy Intl
$262
Find similar
Delta
Aug 23
JFK9:35 pmNew York John F Kennedy Intl
12h 00m
1 stop
MDW8:35 amChicago Midway
Aug 27
MDW1:08 pmChicago Midway
9h 30m
1 stop
JFK11:38 pmNew York John F Kennedy Intl
$267
Find similar

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
Nov 1
JFK6:15 amNew York John F Kennedy Intl
17h 54m
1 stop
MDW11:09 pmChicago Midway
Nov 5
MDW8:00 amChicago Midway
15h 40m
1 stop
JFK12:40 amNew York John F Kennedy Intl
$206
Find similar
Frontier
Aug 27
JFK9:00 amNew York John F Kennedy Intl
6h 01m
1 stop
MDW2:01 pmChicago Midway
Sep 3
MDW3:03 pmChicago Midway
9h 10m
1 stop
JFK1:13 amNew York John F Kennedy Intl
$218
Find similar
Frontier
Sep 24
JFK6:15 amNew York John F Kennedy Intl
10h 43m
1 stop
MDW3:58 pmChicago Midway
Sep 30
MDW2:32 pmChicago Midway
9h 36m
1 stop
JFK1:08 amNew York John F Kennedy Intl
$219
Find similar

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 July 31, 2025.
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 11/1

6:15 am-11:09 pm

1 stop17h 54m

Chicago Midway

Wed 11/5

8:00 am-12:40 am

1 stop15h 40m

$206

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 8/27

9:00 am-2:01 pm

1 stop6h 01m

Chicago Midway

Wed 9/3

3:03 pm-1:13 am

1 stop9h 10m

$218

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 9/24

6:15 am-3:58 pm

1 stop10h 43m

Chicago Midway

Tue 9/30

2:32 pm-1:08 am

1 stop9h 36m

$219

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 12/5

1:00 pm-8:36 pm

1 stop8h 36m

Chicago Midway

Sun 12/7

6:30 am-3:27 pm

1 stop7h 57m

$225

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 9/6

1:01 pm-11:17 pm

1 stop11h 16m

Chicago Midway

Sun 9/7

6:21 am-10:00 am

1 stop26h 39m

$227

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 9/13

11:00 am-12:44 pm

1 stop26h 44m

Chicago Midway

Tue 9/16

2:32 pm-1:08 am

1 stop9h 36m

$228

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 9/5

9:00 am-4:00 pm

1 stop8h 00m

Chicago Midway

Tue 9/9

2:32 pm-1:08 am

1 stop9h 36m

$229

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 8/28

6:59 am-8:22 am

1 stop26h 23m

Chicago Midway

Thu 9/4

6:20 am-1:08 am

1 stop17h 48m

$230

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 8/23

9:35 pm-8:35 am

1 stop12h 00m

Chicago Midway

Wed 8/27

1:08 pm-11:38 pm

1 stop9h 30m

$252

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 8/19

7:45 pm-6:37 pm

1 stop23h 52m

Chicago Midway

Tue 8/26

1:08 pm-11:38 pm

1 stop9h 30m

$262

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 January is also very affordable. Most momondo users find prices during this month for around $292.

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

According to our data, Wednesday 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 Wednesday departure recently was $269. 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 $407.

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 $256 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $344. 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?

As of July 2025, prices for New York John F Kennedy Intl Airport to Chicago Midway Airport flights are approximately 14% 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

$98

Fastest flight time

5h 47m

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 $98. 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 $206.
The fastest flight from New York John F Kennedy Intl Airport to Chicago Midway Airport takes 5h 47m
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.
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 6h 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
7,981 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint John

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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.

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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.

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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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