
Popular airlines from John F. Kennedy Intl. Airport (JFK) to Chicago Midway Airport (MDW)
- Frontier Airlines
Frontier Airlines
- Delta
Delta
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Cheap flights from New York to Chicago (JFK-MDW)
Prices were available within the past 7 days and start at €126 for one-way flights and €254 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, 31 Oct - Mon, 3 Nov
JFK
New York
MDW
Chicago
€254 Return, found 18 hours ago
€254
Return
found 18 hours ago

Fri, 31 Oct - Mon, 3 Nov
JFK
New York
MDW
Chicago
€258 Return, found 18 hours ago
€258
Return
found 18 hours ago

Wed, 29 Oct - Mon, 3 Nov
JFK
New York
MDW
Chicago
€259 Return, found 22 hours ago
€259
Return
found 22 hours ago

Mon, 24 Nov - Tue, 2 Dec
JFK
New York
MDW
Chicago
€264 Return, found 2 days ago
€264
Return
found 2 days ago

Sat, 1 Nov - Mon, 3 Nov
JFK
New York
MDW
Chicago
€287 Return, found 6 days ago
€287
Return
found 6 days ago

Sat, 1 Nov - Mon, 3 Nov
JFK
New York
MDW
Chicago
€291 Return, found 5 days ago
€291
Return
found 5 days ago

Fri, 31 Oct - Mon, 3 Nov
JFK
New York
MDW
Chicago
€295 Return, found 18 hours ago
€295
Return
found 18 hours ago

Sat, 25 Oct - Mon, 27 Oct
JFK
New York
MDW
Chicago
€297 Return, found 15 hours ago
€297
Return
found 15 hours ago

Sat, 1 Nov - Mon, 3 Nov
JFK
New York
MDW
Chicago
€299 Return, found 5 days ago
€299
Return
found 5 days ago

Sat, 25 Oct - Mon, 27 Oct
JFK
New York
MDW
Chicago
€301 Return, found 15 hours ago
€301
Return
found 15 hours ago
Find the cheapest month to fly from New York (JFK) to Chicago (MDW)
April is typically the cheapest month to fly
From €102 - €450 per traveller.
Frequently asked questions
Travel information
Travel information
Origin airport | John F. Kennedy Intl. |
Destination airport | Midway Intl. |
Airlines serving | Delta |
Return price | €253 |
Distance | 1166 km |
Book with confidence
Book with confidence
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 €126 and roundtrip prices from €254. 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.
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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