JFK to MDW (New York to Chicago) Flights

Last Minute Flights from JFK to MDW

Best airfare and ticket deals for JFK to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
JFKChicagoMarch 31 to April 3$382
*Prices include taxes and fees

Cheapest JFK to MDW Flights

Best airfare and ticket deals for JFK to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
JFKChicagoMay 30 to June 5$281
JFKChicagoJune 1 to June 5$282
JFKChicagoMay 29 to May 30$283
JFKChicagoMay 29 to May 30$297
*Prices include taxes and fees
JFK to MDW Flight Details
Origin airport
John F. Kennedy Intl.
Origin airport IATA code
JFK
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
728 mi

Frequently asked questions

Which airlines with flights from JFK Airport to Chicago, IL Airport (MDW-Midway Intl.) allow free cancellation due to COVID-19?
We’ve made it simple to find fares with cancellation flexibility due to COVID-19. After entering your dates and destination, simply click the “No change fee” box. You’ll find it right under the “Flexible change policies” subheading on the left of the screen. Like always, make sure you read through the airline’s terms and conditions carefully before booking your JFK Airport to Chicago, IL Airport (MDW-Midway Intl.) flights.
What airlines fly direct from JFK Airport to Chicago Airport?
Unfortunately, you can’t fly straight from New York, NY Airport (JFK-John F. Kennedy Intl.) to Chicago, IL Airport (MDW-Midway Intl.). Travel to Chicago by locking in a flight with at least one stop in between. If you’re not in a hurry, why not spend a couple of days in your layover city?
How many flights are there from JFK to MDW?
About 12 every day. If you’re in a big rush to reach Chicago, see if you can grab an epic last-minute deal from New York, NY Airport (JFK-John F. Kennedy Intl.) to Chicago, IL Airport (MDW-Midway Intl.) and then lock it in pronto!
How long does it take to fly from New York, NY Airport (JFK-John F. Kennedy Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
Around 5 hours and 24 minutes. Booked on a day flight? Request a window seat and take in the views. Alternatively, if you’re jetting from New York, NY Airport (JFK-John F. Kennedy Intl.) to Chicago, IL Airport (MDW-Midway Intl.) at nighttime, catch some z’s and arrive in Chicago feeling rested and rejuvenated.
What is the flight distance from New York, NY Airport (JFK-John F. Kennedy Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
It’s an easy breezy 730 miles (1150 km) from New York, NY Airport (JFK-John F. Kennedy Intl.) to Chicago, IL Airport (MDW-Midway Intl.), making it a short-haul journey. Try to secure a window seat and be dazzled by the bird’s-eye view of Chicago as you arrive.
How many morning flights are there from JFK to MDW?
Each week, 38 morning services jet out from JFK to MDW, with 35 operated by Delta (DL). If you’d prefer to be soaring through the air before midday, DL’s first flight departs at 6:10AM.
How many afternoon flights are there from JFK to MDW?
With 50 weekly afternoon and evening flights from JFK to MDW, forget about that hotel wake-up call. Check out the offers from Delta (DL) and choose one of the 50 flights per week that jet out after midday. The first departs at 12:30PM.
What is the earliest departure time out of New York to Chicago?
Fly out of JFK at 12:15AM and come in for landing at MDW at 10:50AM. This is the earliest service you can book on this route.
What is the latest departure time out of New York to Chicago?
Book a seat on the 7:50PM flight out of JFK, landing at MDW at 5:07PM, and allow yourself time to deal with those last-minute vacation preparations. This is the latest flight you can take on this route.
What is the average price from New York to Chicago?
Round-trip fares for this route start from around $281. When you’re ready book your trip, we’ll help you score the best possible price. This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

New York to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from New York to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or perhaps simply to treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find the cheapest flights from JFK to MDW, we’ve got you covered here at Flights.com.

We present you with some of the hottest deals on airfare so stop that Google flights search. We want you to spend less on your flight from New York to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.