฿4,825 Cheap Flights from New York (JFK) to Chicago (MDW)

View ฿4,825 flight on Wed, 3 Dec 2025Opens in a new window

Popular airlines from John F. Kennedy International Airport (JFK) to Chicago Midway Airport (MDW)

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Cheap Flights from New York (JFK) to Chicago (MDW)

Prices were available within the past 7 days and start at ฿4,825 for one-way flights and ฿19,880 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 23 Dec - Fri, 26 Dec
JFK
New York
MDW
Chicago
฿19,880 Return, found 4 days ago
฿19,880
Return
found 4 days ago
Select Delta flight, departing Tue, 23 Dec from New York to Chicago, returning Fri, 26 Dec, priced at ฿19,880 found 4 days ago
Delta
Tue, 23 Dec - Fri, 26 Dec
JFK
New York
MDW
Chicago
฿20,690 Return, found 4 days ago
฿20,690
Return
found 4 days ago
Select Delta flight, departing Tue, 23 Dec from New York to Chicago, returning Fri, 26 Dec, priced at ฿20,690 found 4 days ago
Delta
Tue, 23 Dec - Fri, 26 Dec
JFK
New York
MDW
Chicago
฿21,500 Return, found 4 days ago
฿21,500
Return
found 4 days ago
Select Delta flight, departing Tue, 23 Dec from New York to Chicago, returning Fri, 26 Dec, priced at ฿21,500 found 4 days ago
Delta
Tue, 23 Dec - Fri, 26 Dec
JFK
New York
MDW
Chicago
฿22,315 Return, found 4 days ago
฿22,315
Return
found 4 days ago
Select Delta flight, departing Tue, 23 Dec from New York to Chicago, returning Fri, 26 Dec, priced at ฿22,315 found 4 days ago
Delta
Tue, 23 Dec - Fri, 26 Dec
JFK
New York
MDW
Chicago
฿22,805 Return, found 4 days ago
฿22,805
Return
found 4 days ago
Select Delta flight, departing Tue, 23 Dec from New York to Chicago, returning Fri, 26 Dec, priced at ฿22,805 found 4 days ago

Find the cheapest month to fly from New York (JFK) to Chicago (MDW)

April is typically the cheapest month to fly

From ฿3,842 - ฿16,500 per traveller.

Graph displaying average flight prices per month

Flight from New York to Chicago route information
Origin airport
John F. Kennedy Intl.
Destination airport
Midway Intl.
Return price
฿19,880
Distance
1166 km

Perfect flights from New York to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from New York to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible John F. Kennedy Intl. to Midway Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿4,825 and roundtrip prices from ฿19,880. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Midway Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Chicago.

Frequently asked questions

How much is a flight from JFK Airport to MDW?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from JFK to Midway Airport was ฿19,880. Cheap fares don't stick around for long, so make sure you book yours today. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from JFK to Midway Intl. Airport (MDW)?
Most flights can be conveniently cancelled online, but whether or not you incur a fee differs between airlines. If you do have to cancel your trip, follow the instructions in the Customer Service Portal.
How do I find cheap flights from JFK to Midway Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for JFK to MDW flights, you'll see a "no change fees" filter for you to select.
How far is the flight from John F. Kennedy Intl. Airport (JFK) to MDW?
It's just 1,150 kilometres between JFK and Chicago Airport. Chances are you'll spend more time travelling to and from the airport than actually flying!
Which airlines fly direct from JFK to Chicago Airport?
If you want to travel straight from JFK Airport to Midway Intl. Airport (MDW), you'll need to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly on this route.
Are John F. Kennedy Intl. Airport (JFK) to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
Late planners can occasionally score a bargain, with some of the cheapest fares from JFK Airport to Midway Airport appearing a few weeks before the departure date. If you'd rather plan ahead of time, Expedia compares and updates all the best flight deals frequently — as early as 12 months in advance in some cases. It does depend on the carrier though, as not all airlines advertise prices so far in advance.

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