
Popular airlines from John F. Kennedy Intl. Airport (JFK) to Chicago Midway Airport (MDW)
- Frontier Airlines
Frontier Airlines
- Delta
Delta
- Plan, book, fly with confidence
trending down icon Be in the knowGet alerts if flight prices drop or rise*bex rewards loyalty icon Book smarterSave up to 15% on select hotels after you book a flight*payments icon
Cheap flights from New York to Chicago (JFK-MDW)
Prices were available within the past 7 days and start at €128 for one-way flights and €255 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, 13 Sep - Mon, 15 Sep
JFK
New York
MDW
Chicago
€255 Return, found 5 days ago
€255
Return
found 5 days ago

Thu, 4 Sep - Mon, 8 Sep
JFK
New York
MDW
Chicago
€256 Return, found 14 hours ago
€256
Return
found 14 hours ago

Thu, 4 Sep - Wed, 10 Sep
JFK
New York
MDW
Chicago
€263 Return, found 4 days ago
€263
Return
found 4 days ago

Thu, 4 Sep - Mon, 8 Sep
JFK
New York
MDW
Chicago
€264 Return, found 5 days ago
€264
Return
found 5 days ago

Fri, 5 Sep - Mon, 8 Sep
JFK
New York
MDW
Chicago
€290 Return, found 5 days ago
€290
Return
found 5 days ago

Fri, 31 Oct - Mon, 3 Nov
JFK
New York
MDW
Chicago
€297 Return, found 4 days ago
€297
Return
found 4 days ago

Thu, 4 Sep - Mon, 8 Sep
JFK
New York
MDW
Chicago
€298 Return, found 5 days ago
€298
Return
found 5 days ago

Thu, 4 Sep - Wed, 10 Sep
JFK
New York
MDW
Chicago
€303 Return, found 4 days ago
€303
Return
found 4 days ago

Thu, 4 Sep - Mon, 8 Sep
JFK
New York
MDW
Chicago
€305 Return, found 5 days ago
€305
Return
found 5 days ago

Fri, 5 Sep - Mon, 8 Sep
JFK
New York
MDW
Chicago
€315 Return, found 5 days ago
€315
Return
found 5 days ago
Find the cheapest month to fly from New York (JFK) to Chicago (MDW)
April is typically the cheapest month to fly
From €102 - €438 per traveller.
Graph displaying average flight prices per month
Origin airport | John F. Kennedy Intl. |
Destination airport | Midway Intl. |
Airlines serving | Delta |
Return price | €255 |
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 €128 and roundtrip prices from €255. 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
Explore a world of travel with Expedia
- Trending Routes
- 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 Paris (JFK - CDG)
- New York to Istanbul (JFK - IST)
- New York to Dublin (JFK - DUB)
- New York to Tokyo (JFK - NRT)
- New York to Buffalo (JFK - BUF)
- New York to Shannon (JFK - SNN)
- New York to Nashville (JFK - BNA)
- New York to Athens (JFK - ATH)
- New York to London (JFK - LHR)
- New York to Lisbon (JFK - LIS)
Top Flight Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Chicago
- Flights to San Diego
- Flights to Myrtle Beach
- Flights to Los Angeles
- Flights to Ocean City
- Flights to San Francisco
- Flights to Miami
- Flights to Destin
- Flights to Nashville
- Flights to Panama City Beach
- Flights to Atlantic City
- Flights to Pigeon Forge
- Flights to Honolulu
- Flights to Houston
- Flights to Atlanta
- Flights to Seattle
- Flights to Virginia Beach
Expedia's Latest Trends
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 Dublin (DUB) to Buffalo (BUF)
- Flights from Rochester (ROC) to New York (JFK)
- 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 Los Angeles (LAX) to Chicago (ORD)
- 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 Toronto (YYZ) to Chicago (ORD)
- Flights from New York (JFK) to Latham (ALB)
*Available to Expedia members.