£109 Cheap Flights from New York (JFK) to Chicago (MDW)

View £109 flight on Wed, 16 Sept 2026Opens 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 £109 for one-way flights and £315 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 16 Sept - Fri, 18 Sept
JFK
New York
MDW
Chicago
£315 Return, found 1 day ago
£315
Return
found 1 day ago
Select Delta flight, departing Wed, 16 Sept from New York to Chicago, returning Fri, 18 Sept, priced at £315 found 1 day ago
Delta
Wed, 16 Sept - Fri, 18 Sept
JFK
New York
MDW
Chicago
£328 Return, found 1 day ago
£328
Return
found 1 day ago
Select Delta flight, departing Wed, 16 Sept from New York to Chicago, returning Fri, 18 Sept, priced at £328 found 1 day ago
Delta
Sat, 2 May - Sun, 3 May
JFK
New York
MDW
Chicago
£337 Return, found 1 day ago
£337
Return
found 1 day ago
Select Delta flight, departing Sat, 2 May from New York to Chicago, returning Sun, 3 May, priced at £337 found 1 day ago
Delta
Fri, 17 Jul - Fri, 24 Jul
JFK
New York
MDW
Chicago
£338 Return, found 2 days ago
£338
Return
found 2 days ago
Select Delta flight, departing Fri, 17 Jul from New York to Chicago, returning Fri, 24 Jul, priced at £338 found 2 days ago
Delta
Wed, 16 Sept - Fri, 18 Sept
JFK
New York
MDW
Chicago
£351 Return, found 1 day ago
£351
Return
found 1 day ago
Select Delta flight, departing Wed, 16 Sept from New York to Chicago, returning Fri, 18 Sept, priced at £351 found 1 day ago
Delta
Wed, 16 Sept - Fri, 18 Sept
JFK
New York
MDW
Chicago
£367 Return, found 1 day ago
£367
Return
found 1 day ago
Select Delta flight, departing Wed, 16 Sept from New York to Chicago, returning Fri, 18 Sept, priced at £367 found 1 day ago
Delta
Wed, 16 Sept - Fri, 18 Sept
JFK
New York
MDW
Chicago
£374 Return, found 1 day ago
£374
Return
found 1 day ago
Select Delta flight, departing Wed, 16 Sept from New York to Chicago, returning Fri, 18 Sept, priced at £374 found 1 day ago
Delta
Wed, 16 Sept - Fri, 18 Sept
JFK
New York
MDW
Chicago
£380 Return, found 1 day ago
£380
Return
found 1 day ago
Select Delta flight, departing Wed, 16 Sept from New York to Chicago, returning Fri, 18 Sept, priced at £380 found 1 day ago
Delta
Fri, 17 Jul - Fri, 24 Jul
JFK
New York
MDW
Chicago
£383 Return, found 2 days ago
£383
Return
found 2 days ago
Select Delta flight, departing Fri, 17 Jul from New York to Chicago, returning Fri, 24 Jul, priced at £383 found 2 days ago
Delta
Sat, 2 May - Sun, 3 May
JFK
New York
MDW
Chicago
£397 Return, found 1 day ago
£397
Return
found 1 day ago
Select Delta flight, departing Sat, 2 May from New York to Chicago, returning Sun, 3 May, priced at £397 found 1 day ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from £233
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from £233

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 £315. 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.

Frequently asked questions

How do I find cheap flights from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 14 connecting flights per day from New York, NY (JFK-John F. Kennedy Intl.) (JFK) to Chicago, IL (MDW-Midway Intl.) (MDW). Some common connection points include Hartsfield-Jackson Atlanta Intl. (ATL), Detroit Metropolitan Wayne County (DTW), and Minneapolis - St. Paul Intl. (MSP).
What is the earliest flight from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from John F. Kennedy Intl. (JFK) to Midway Intl. (MDW) typically departs at approximately 6:00 AM local time, operated by Delta Air Lines. This is a seasonal service active in June. An early departure like this can help you maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
For flights from John F. Kennedy Intl. (JFK) to Midway Intl. (MDW), you'll typically find the most options on a Thursday, with around 9 flights available. Flight schedules are fairly consistent throughout the week, with Thursday offering slightly more flights than other days. Major airlines on this route include Delta Air Lines and Frontier Airlines.
What are the most popular departure times for flights from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from John F. Kennedy Intl. (JFK) to Midway Intl. (MDW) are between 12pm and 3pm. About 41% of passengers prefer this time. Delta Air Lines and Frontier Airlines offer flights during this window. Many travelers find this midday window convenient as it allows for a productive morning before heading to the airport, and you'll arrive in Chicago in the afternoon with plenty of time to settle in.
How long does it take to fly from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
Flights from JFK to MDW with one stop typically take around 6 hours 30 minutes, covering approximately 729 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for JFK to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from John F. Kennedy Intl. (JFK)?
From John F. Kennedy Intl. (JFK), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Ronald Reagan Washington National (DCA), Raleigh - Durham Intl. (RDU), Cincinnati - Northern Kentucky Intl. (CVG) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
John F. Kennedy Intl.
Destination airport
Midway Intl.
Return price
£314
Distance
1166 km

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