
Popular airlines from John F. Kennedy Intl. Airport (JFK) to Chicago Midway Airport (MDW)
- Frontier Airlines
Frontier Airlines
- Delta
Delta
- Be in the knowGet alerts if flight prices drop or rise*
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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 €261 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, 5 Dec - Mon, 8 Dec
JFK
New York
MDW
Chicago
€261 Return, found 2 days ago
€261
Return
found 2 days ago

Fri, 5 Dec - Mon, 8 Dec
JFK
New York
MDW
Chicago
€266 Return, found 21 hours ago
€266
Return
found 21 hours ago

Fri, 9 Jan - Fri, 16 Jan
JFK
New York
MDW
Chicago
€268 Return, found 1 day ago
€268
Return
found 1 day ago

Fri, 5 Dec - Mon, 8 Dec
JFK
New York
MDW
Chicago
€291 Return, found 2 days ago
€291
Return
found 2 days ago

Fri, 5 Dec - Mon, 8 Dec
JFK
New York
MDW
Chicago
€298 Return, found 21 hours ago
€298
Return
found 21 hours ago

Fri, 9 Jan - Fri, 16 Jan
JFK
New York
MDW
Chicago
€311 Return, found 1 day ago
€311
Return
found 1 day ago

Fri, 5 Dec - Mon, 8 Dec
JFK
New York
MDW
Chicago
€315 Return, found 21 hours ago
€315
Return
found 21 hours ago

Fri, 5 Dec - Mon, 8 Dec
JFK
New York
MDW
Chicago
€328 Return, found 21 hours ago
€328
Return
found 21 hours ago

Fri, 5 Dec - Mon, 8 Dec
JFK
New York
MDW
Chicago
€358 Return, found 21 hours ago
€358
Return
found 21 hours ago

Fri, 5 Dec - Mon, 8 Dec
JFK
New York
MDW
Chicago
€371 Return, found 21 hours ago
€371
Return
found 21 hours ago
Find the cheapest month to fly from New York (JFK) to Chicago (MDW)
April is typically the cheapest month to fly
From €104 - €460 per traveller.
Origin airport | John F. Kennedy Intl. |
|---|---|
Destination airport | Midway Intl. |
Airlines serving | Delta |
Return price | €261 |
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 €126 and roundtrip prices from €261. 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.
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