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Cheap flights from New York John F Kennedy Intl Airport to Chicago from $71

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 10/31. 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
6:20 am - 12:41 pmJFK-MDW
7h 21m1 stop
Frontier Logo
1:56 pm - 12:33 amMDW-JFK
9h 37m1 stop
$133Frontier
Find Deal
Wed, Nov 5 - Tue, Nov 11
Frontier Logo
6:20 am - 11:38 amJFK-MDW
6h 18m1 stop
Frontier Logo
1:37 pm - 12:33 amMDW-JFK
9h 56m1 stop
$134Frontier
Find Deal
Tue, Nov 11 - Thu, Nov 13
Frontier Logo
6:20 am - 6:39 pmJFK-MDW
13h 19m1 stop
Frontier Logo
1:56 pm - 12:33 amMDW-JFK
9h 37m1 stop
$137Frontier
Find Deal
Fri, Nov 7 - Tue, Nov 11
Frontier Logo
6:25 am - 11:38 amJFK-MDW
6h 13m1 stop
Frontier Logo
1:37 pm - 12:33 amMDW-JFK
9h 56m1 stop
$139Frontier
Find Deal
Tue, Oct 28 - Sat, Nov 1
Frontier Logo
9:00 am - 6:39 pmJFK-MDW
10h 39m1 stop
Frontier Logo
6:06 pm - 3:00 pmMDW-JFK
19h 54m1 stop
$141Frontier
Find Deal
Sat, Nov 1 - Mon, Nov 3
Frontier Logo
1:01 pm - 10:47 pmJFK-MDW
10h 46m1 stop
Frontier Logo
1:37 pm - 12:33 amMDW-JFK
9h 56m1 stop
$143Frontier
Find Deal
Sat, Oct 25 - Sat, Nov 1
Frontier Logo
6:20 am - 12:41 pmJFK-MDW
7h 21m1 stop
Frontier Logo
2:06 pm - 12:33 amMDW-JFK
9h 27m1 stop
$144Frontier
Find Deal
Wed, Nov 5 - Wed, Nov 12
Frontier Logo
4:00 pm - 4:57 pmJFK-MDW
25h 57m1 stop
Frontier Logo
1:37 pm - 12:33 amMDW-JFK
9h 56m1 stop
$145Frontier
Find Deal
Thu, Nov 13 - Mon, Nov 17
Frontier Logo
12:59 pm - 11:20 pmJFK-MDW
11h 21m1 stop
Frontier Logo
5:28 pm - 10:29 amMDW-JFK
16h 01m1 stop
$146Frontier
Find Deal
Sat, Oct 25 - Mon, Oct 27
Frontier Logo
10:00 am - 6:39 pmJFK-MDW
9h 39m1 stop
Frontier Logo
9:27 am - 10:29 amMDW-JFK
24h 02m1 stop
$149Frontier
Find Deal
Fri, Nov 14 - Mon, Nov 17

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 5
JFK6:20 amNew York John F Kennedy Intl
7h 21m
1 stop
MDW12:41 pmChicago Midway
Nov 11
MDW1:56 pmChicago Midway
9h 37m
1 stop
JFK12:33 amNew York John F Kennedy Intl
$133
Find similar
Frontier
Nov 11
JFK6:20 amNew York John F Kennedy Intl
6h 18m
1 stop
MDW11:38 amChicago Midway
Nov 13
MDW1:37 pmChicago Midway
9h 56m
1 stop
JFK12:33 amNew York John F Kennedy Intl
$134
Find similar
Frontier
Nov 7
JFK6:20 amNew York John F Kennedy Intl
13h 19m
1 stop
MDW6:39 pmChicago Midway
Nov 11
MDW1:56 pmChicago Midway
9h 37m
1 stop
JFK12:33 amNew York John F Kennedy Intl
$137
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 October 20, 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

Wed 11/5

6:20 am-12:41 pm

1 stop7h 21m

Chicago Midway

Tue 11/11

1:56 pm-12:33 am

1 stop9h 37m

$133

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 11/11

6:20 am-11:38 am

1 stop6h 18m

Chicago Midway

Thu 11/13

1:37 pm-12:33 am

1 stop9h 56m

$134

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 11/7

6:20 am-6:39 pm

1 stop13h 19m

Chicago Midway

Tue 11/11

1:56 pm-12:33 am

1 stop9h 37m

$137

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 10/28

6:25 am-11:38 am

1 stop6h 13m

Chicago Midway

Sat 11/1

1:37 pm-12:33 am

1 stop9h 56m

$139

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 11/1

9:00 am-6:39 pm

1 stop10h 39m

Chicago Midway

Mon 11/3

6:06 pm-3:00 pm

1 stop19h 54m

$141

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 10/25

1:01 pm-10:47 pm

1 stop10h 46m

Chicago Midway

Sat 11/1

1:37 pm-12:33 am

1 stop9h 56m

$143

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 11/5

6:20 am-12:41 pm

1 stop7h 21m

Chicago Midway

Wed 11/12

2:06 pm-12:33 am

1 stop9h 27m

$144

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 11/13

4:00 pm-4:57 pm

1 stop25h 57m

Chicago Midway

Mon 11/17

1:37 pm-12:33 am

1 stop9h 56m

$145

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 10/25

12:59 pm-11:20 pm

1 stop11h 21m

Chicago Midway

Mon 10/27

5:28 pm-10:29 am

1 stop16h 01m

$146

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 11/14

10:00 am-6:39 pm

1 stop9h 39m

Chicago Midway

Mon 11/17

9:27 am-10:29 am

1 stop24h 02m

$149

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 typical price of a round-trip flight between New York John F Kennedy Intl Airport and Chicago Midway Airport?

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 September is also very affordable. Most momondo users find prices during this month for around $231.

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 $279. 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 $421.

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 $253 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $359. 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 October 2025, prices for New York John F Kennedy Intl Airport to Chicago Midway Airport flights are approximately 109% more expensive 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

Direct flights

None
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.
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  • 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 04m, 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
7,978 reviews
Search Delta flights

Traveling to a place near Chicago?

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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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