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Cheap flights from New York John F Kennedy Intl Airport to Chicago from $116

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 9/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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.
Delta Logo
1:00 pm - 6:33 pm
JFK
-
MDW
6h 33m
1 stop
Delta Logo
1:19 pm - 8:09 pm
MDW
-
JFK
5h 50m
1 stop
$295Delta
Thu, Sep 17 - Mon, Sep 21
Delta Logo
3:40 pm - 10:36 pm
JFK
-
MDW
7h 56m
1 stop
Delta Logo
9:24 am - 5:48 pm
MDW
-
JFK
7h 24m
1 stop
$295Delta
Wed, Aug 19 - Wed, Aug 26
Delta Logo
6:00 am - 9:07 am
JFK
-
MDW
4h 07m
1 stop
Delta Logo
1:00 pm - 10:03 pm
MDW
-
JFK
8h 03m
1 stop
$295Delta
Thu, Oct 1 - Fri, Oct 2
Delta Logo
1:00 pm - 6:33 pm
JFK
-
MDW
6h 33m
1 stop
Delta Logo
1:19 pm - 8:09 pm
MDW
-
JFK
5h 50m
1 stop
$295Delta
Wed, Sep 30 - Sat, Oct 3
Delta Logo
7:15 am - 12:39 pm
JFK
-
MDW
6h 24m
1 stop
Delta Logo
1:19 pm - 8:09 pm
MDW
-
JFK
5h 50m
1 stop
$295Delta
Tue, Sep 29 - Wed, Sep 30
Delta Logo
8:35 am - 3:24 pm
JFK
-
MDW
7h 49m
1 stop
Delta Logo
5:10 pm - 12:59 am
MDW
-
JFK
6h 49m
1 stop
$295Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
10:55 am - 4:15 pm
JFK
-
MDW
6h 20m
1 stop
Delta Logo
1:19 pm - 8:09 pm
MDW
-
JFK
5h 50m
1 stop
$295Delta
Tue, Sep 15 - Wed, Sep 16
Delta Logo
10:55 am - 3:24 pm
JFK
-
MDW
5h 29m
1 stop
Delta Logo
1:19 pm - 8:09 pm
MDW
-
JFK
5h 50m
1 stop
$295Delta
Wed, Sep 9 - Mon, Sep 14
Frontier Logo
1:00 pm - 5:51 pm
JFK
-
MDW
5h 51m
1 stop
Frontier Logo
6:46 pm - 11:50 am
MDW
-
JFK
16h 04m
1 stop
$349Frontier
Mon, Sep 14 - Mon, Sep 21
Frontier Logo
1:00 pm - 5:51 pm
JFK
-
MDW
5h 51m
1 stop
Frontier Logo
6:46 pm - 11:50 am
MDW
-
JFK
16h 04m
1 stop
$377Frontier
Mon, Sep 14 - Sun, Sep 27

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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
Sep 29
JFK10:55 amNew York John F Kennedy Intl
6h 20m
1 stop
MDW4:15 pmChicago Midway
Oct 6
MDW6:04 amChicago Midway
4h 56m
1 stop
JFK12:00 pmNew York John F Kennedy Intl
$295
Delta
Sep 12
JFK1:00 pmNew York John F Kennedy Intl
4h 57m
1 stop
MDW4:57 pmChicago Midway
Sep 14
MDW1:19 pmChicago Midway
5h 50m
1 stop
JFK8:09 pmNew York John F Kennedy Intl
$297
Delta
Sep 15
JFK10:55 amNew York John F Kennedy Intl
6h 20m
1 stop
MDW4:15 pmChicago Midway
Dec 12
MDW4:19 pmChicago Midway
7h 44m
1 stop
JFK1:03 amNew York John F Kennedy Intl
$300

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
Sep 14
JFK1:00 pmNew York John F Kennedy Intl
5h 51m
1 stop
MDW5:51 pmChicago Midway
Sep 21
MDW6:46 pmChicago Midway
16h 04m
1 stop
JFK11:50 amNew York John F Kennedy Intl
$349
Frontier
Sep 16
JFK1:00 pmNew York John F Kennedy Intl
5h 51m
1 stop
MDW5:51 pmChicago Midway
Sep 27
MDW6:46 pmChicago Midway
16h 04m
1 stop
JFK11:50 amNew York John F Kennedy Intl
$379
Frontier
Sep 12
JFK1:00 pmNew York John F Kennedy Intl
5h 51m
1 stop
MDW5:51 pmChicago Midway
Sep 13
MDW6:46 pmChicago Midway
16h 04m
1 stop
JFK11:50 amNew York John F Kennedy Intl
$384

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 August 1, 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

Cheapest round-trip

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 9/17

1:00 pm-6:33 pm

1 stop6h 33m

Chicago Midway

Mon 9/21

1:19 pm-8:09 pm

1 stop5h 50m

$295

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 8/19

3:40 pm-10:36 pm

1 stop7h 56m

Chicago Midway

Wed 8/26

9:24 am-5:48 pm

1 stop7h 24m

$295

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 10/1

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Fri 10/2

1:00 pm-10:03 pm

1 stop8h 03m

$295

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 9/30

1:00 pm-6:33 pm

1 stop6h 33m

Chicago Midway

Sat 10/3

1:19 pm-8:09 pm

1 stop5h 50m

$295

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 9/29

7:15 am-12:39 pm

1 stop6h 24m

Chicago Midway

Wed 9/30

1:19 pm-8:09 pm

1 stop5h 50m

$295

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 10/3

8:35 am-3:24 pm

1 stop7h 49m

Chicago Midway

Mon 10/5

5:10 pm-12:59 am

1 stop6h 49m

$295

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 9/15

10:55 am-4:15 pm

1 stop6h 20m

Chicago Midway

Wed 9/16

1:19 pm-8:09 pm

1 stop5h 50m

$295
Quickest round-trip

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 9/9

10:55 am-3:24 pm

1 stop5h 29m

Chicago Midway

Mon 9/14

1:19 pm-8:09 pm

1 stop5h 50m

$295

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 9/14

1:00 pm-5:51 pm

1 stop5h 51m

Chicago Midway

Mon 9/21

6:46 pm-11:50 am

1 stop16h 04m

$349

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 9/14

1:00 pm-5:51 pm

1 stop5h 51m

Chicago Midway

Sun 9/27

6:46 pm-11:50 am

1 stop16h 04m

$377

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday 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 Thursday departure recently was $293. 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 $405.

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 $246 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $377. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

4h 23m

Direct flights

None
The fastest flight from New York John F Kennedy Intl Airport to Chicago Midway Airport takes 4h 23m
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

Frequently asked questions about flying from New York John F Kennedy Intl Airport to 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 23m, 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
7.8
8,497 reviews
Search Delta flights

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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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