Featured airlines
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 15% on select hotels after you book a flight*
Plan, book, fly with confidence
Cheap flights from New York to Chicago (JFK-MDW)
Prices were available within the past 7 days and start at €136 for one-way flights and €267 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, 13 Nov - Sat, 16 Nov
JFK
New York
MDW
Chicago
€267 Return, found 21 hours ago
€267
Return
found 21 hours ago
Wed, 13 Nov - Sat, 16 Nov
JFK
New York
MDW
Chicago
€272 Return, found 21 hours ago
€272
Return
found 21 hours ago
Sat, 27 Jul - Mon, 29 Jul
JFK
New York
MDW
Chicago
€273 Return, found 6 days ago
€273
Return
found 6 days ago
Wed, 13 Nov - Sat, 16 Nov
JFK
New York
MDW
Chicago
€277 Return, found 21 hours ago
€277
Return
found 21 hours ago
Wed, 13 Nov - Sat, 16 Nov
JFK
New York
MDW
Chicago
€281 Return, found 21 hours ago
€281
Return
found 21 hours ago
Sat, 27 Jul - Mon, 29 Jul
JFK
New York
MDW
Chicago
€292 Return, found 4 hours ago
€292
Return
found 4 hours ago
Mon, 1 Jul - Sat, 7 Sep
JFK
New York
MDW
Chicago
€310 Return, found 4 days ago
€310
Return
found 4 days ago
Mon, 1 Jul - Sat, 7 Sep
JFK
New York
MDW
Chicago
€334 Return, found 4 days ago
€334
Return
found 4 days ago
Mon, 1 Jul - Sat, 7 Sep
JFK
New York
MDW
Chicago
€348 Return, found 4 days ago
€348
Return
found 4 days ago
Tue, 2 Jul - Tue, 24 Sep
JFK
New York
MDW
Chicago
€351 Return, found 2 days ago
€351
Return
found 2 days ago
Origin airport | John F. Kennedy Intl. |
Destination airport | Midway Intl. |
Airlines serving | Delta |
Return price | €267 |
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 €136 and roundtrip prices from €267. 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
- Trending Routes
- Trending Flights
- Top Flights Destinations
- More Airlines
- Cheap Flights from Other Airports
- Expedia's Latest Trends
Top Routes from New York
- New York to Los Angeles (JFK - LAX)
- New York to Miami (JFK - MIA)
- New York to Fort Lauderdale (JFK - FLL)
- New York to Paris (JFK - CDG)
- New York to Savannah (JFK - SAV)
- New York to Málaga (JFK - AGP)
- New York to Dublin (JFK - DUB)
- New York to Shannon (JFK - SNN)
- New York to Nashville (JFK - BNA)
- New York to Vancouver (JFK - YVR)
- New York to Athens (JFK - ATH)
- New York to London (JFK - LHR)
Top Routes from New York
Top Flight Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Panama City Beach
- Flights to Chicago
- Flights to Myrtle Beach
- Flights to San Diego
- Flights to Los Angeles
- Flights to Destin
- Flights to Miami
- Flights to Nashville
- Flights to Boston
- Flights to Houston
- Flights to San Francisco
- Flights to Honolulu
- Flights to Key West
- Flights to New Orleans
- Flights to Atlanta
- Flights to Seattle
- Flights to San Antonio
Hotels
Flights
Flights from New York (JFK) to Chicago (ORD)Flights from Buffalo (BUF) to Boston (BOS)Flights from Dublin (DUB) to North Syracuse (SYR)Flights from Shannon (SNN) to Chicago (ORD)Flights from New York (JFK) to Buffalo (BUF)Flights from Buffalo (BUF) to Dublin (DUB)Flights from Boston (BOS) to Buffalo (BUF)Flights from Newark (EWR) to Buffalo (BUF)Flights from Dublin (DUB) to Buffalo (BUF)Flights from Las Vegas (LAS) to Chicago (ORD)Flights from New York (JFK) to Niagara Falls (IAG)Flights from Vancouver (YVR) to Niagara Falls (IAG)Flights from Toronto (YYZ) to Buffalo (BUF)Flights from Dublin (DUB) to Chicago (ORD)Flights from North Syracuse (SYR) to New York (JFK)Flights from Cork (ORK) to Rochester (ROC)Flights from Rochester (ROC) to Dublin (DUB)Flights from Shannon (SNN) to Buffalo (BUF)Flights from Buffalo (BUF) to New York (JFK)Flights from Cork (ORK) to Chicago (ORD)Flights from North Syracuse (SYR) to Dublin (DUB)Flights from New York (LGA) to Chicago (ORD)Flights from New York (JFK) to Rochester (ROC)Flights from New York (JFK) to Latham (ALB)Flights from Newark (EWR) to Latham (ALB)
*Available to Expedia members.