£112 Cheap Flights from New York (JFK) to Chicago (MDW)

View £112 flight on Sat, 24 May 2025Opens in a new window

Popular airlines from John F. Kennedy International Airport (JFK) to Chicago Midway Airport (MDW)

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Cheap Flights from New York (JFK) to Chicago (MDW)

Prices were available within the past 7 days and start at £112 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Flight from New York to Chicago route information
Origin airport
John F. Kennedy Intl.
Destination airport
Midway Intl.
Distance
1166 km

Compare flights from New York to Chicago easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from New York to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to Midway Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from John F. Kennedy Intl. to Midway Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from John F. Kennedy Intl. (JFK) to Midway Intl. (MDW) 

The easiest way to view the best deals on flights from New York to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from John F. Kennedy Intl. to Midway Intl. start at just and range up to .  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near New York and Chicago
  • booking your flight during , the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your New York to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from John F. Kennedy Intl. to Midway Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Frequently asked questions

How much is a flight from JFK Airport to MDW?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from JFK to Midway Airport was . Cheap fares don’t stick around for long, so make sure you book yours today. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from JFK to Midway Intl. Airport (MDW)?
Most flights can be conveniently cancelled online, but whether or not you incur a fee differs between airlines. If you do have to cancel your trip, follow the instructions in the Customer Service Portal.
How do I find cheap flights from JFK to Midway Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for JFK to MDW flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from John F. Kennedy Intl. Airport (JFK) to MDW?
It’s just 1,150 kilometres between JFK and Chicago Airport. Chances are you’ll spend more time travelling to and from the airport than actually flying!
Which airlines fly direct from JFK to Chicago Airport?
If you want to travel straight from JFK Airport to Midway Intl. Airport (MDW), you’ll need to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly on this route.
Are John F. Kennedy Intl. Airport (JFK) to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
Late planners can occasionally score a bargain, with some of the cheapest fares from JFK Airport to Midway Airport appearing a few weeks before the departure date. If you’d rather plan ahead of time, Expedia compares and updates all the best flight deals frequently — as early as 12 months in advance in some cases. It does depend on the carrier though, as not all airlines advertise prices so far in advance.

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