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£110 Cheap Flights from New York (JFK) to Chicago (MDW)

View £110 flight on Fri, 2 Oct 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 £110 for one-way flights and £218 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 1 Sept - Tue, 15 Sept
JFK
New York
MDW
Chicago
£218 Return, found 5 days ago
£218
Return
found 5 days ago
Select Delta flight, departing Tue, 1 Sept from New York to Chicago, returning Tue, 15 Sept, priced at £218 found 5 days ago
Delta
Tue, 11 Aug - Mon, 24 Aug
JFK
New York
MDW
Chicago
£219 Return, found 5 days ago
£219
Return
found 5 days ago
Select Delta flight, departing Tue, 11 Aug from New York to Chicago, returning Mon, 24 Aug, priced at £219 found 5 days ago
Delta
Tue, 18 Aug - Wed, 26 Aug
JFK
New York
MDW
Chicago
£220 Return, found 22 hours ago
£220
Return
found 22 hours ago
Select Delta flight, departing Tue, 18 Aug from New York to Chicago, returning Wed, 26 Aug, priced at £220 found 22 hours ago
Delta
Wed, 12 Aug - Mon, 24 Aug
JFK
New York
MDW
Chicago
£234 Return, found 5 days ago
£234
Return
found 5 days ago
Select Delta flight, departing Wed, 12 Aug from New York to Chicago, returning Mon, 24 Aug, priced at £234 found 5 days ago
Delta
Sat, 8 Aug - Tue, 18 Aug
JFK
New York
MDW
Chicago
£237 Return, found 5 days ago
£237
Return
found 5 days ago
Select Delta flight, departing Sat, 8 Aug from New York to Chicago, returning Tue, 18 Aug, priced at £237 found 5 days ago
Delta
Sat, 8 Aug - Mon, 24 Aug
JFK
New York
MDW
Chicago
£238 Return, found 5 days ago
£238
Return
found 5 days ago
Select Delta flight, departing Sat, 8 Aug from New York to Chicago, returning Mon, 24 Aug, priced at £238 found 5 days ago
Delta
Fri, 7 Aug - Tue, 18 Aug
JFK
New York
MDW
Chicago
£248 Return, found 5 days ago
£248
Return
found 5 days ago
Select Delta flight, departing Fri, 7 Aug from New York to Chicago, returning Tue, 18 Aug, priced at £248 found 5 days ago
Delta
Wed, 12 Aug - Sat, 22 Aug
JFK
New York
MDW
Chicago
£249 Return, found 5 days ago
£249
Return
found 5 days ago
Select Delta flight, departing Wed, 12 Aug from New York to Chicago, returning Sat, 22 Aug, priced at £249 found 5 days ago
Delta
Sat, 22 Aug - Mon, 24 Aug
JFK
New York
MDW
Chicago
£251 Return, found 1 day ago
£251
Return
found 1 day ago
Select Delta flight, departing Sat, 22 Aug from New York to Chicago, returning Mon, 24 Aug, priced at £251 found 1 day ago
Delta
Sat, 8 Aug - Sat, 22 Aug
JFK
New York
MDW
Chicago
£252 Return, found 5 days ago
£252
Return
found 5 days ago
Select Delta flight, departing Sat, 8 Aug from New York to Chicago, returning Sat, 22 Aug, priced at £252 found 5 days 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. Average driving time to city centre is 23 minutes. Flights from £283
ORD
O'Hare Intl.
Average driving time to city centre23 min
Flights from £283

Find the cheapest month to fly from New York (JFK) to Chicago (MDW)

February is typically the cheapest month to fly

From £93 - £513 per traveller.

Frequently asked questions

How much does a flight from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find one-way and return flights from JFK to MDW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when JFK to MDW ticket fares go up or down.
What is the cheapest month to fly from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from JFK to MDW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter JFK to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
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 no direct flights from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.). However, you'll find approximately 14 connecting flights per day. 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 New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs around 6:00 AM. This service is operated by Delta. This is a seasonal service, active in October and November. An early departure like this can help you make the most of 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.)?
You'll typically find the most flights from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.) on a Wednesday, with around 9 flights available. This gives you a good selection for your travel plans. Major airlines on this route include Delta and Frontier Airlines. Flight schedules are fairly consistent throughout the week, so you'll have plenty of options no matter when you choose to fly.
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 in the afternoon, from 12pm to 3pm. Many major carriers, including Delta and Frontier Airlines, offer flights during this window. Many travellers prefer this time as it allows for a full morning before heading to the airport and an afternoon arrival at your destination.
How long does it take to fly from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are no nonstop flights from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.). For flights with one stop, you can expect the journey to take around 6 hours 30 minutes. If your flight has two or more stops, the travel time typically increases to about 10 hours. The distance between JFK and MDW is approximately 1,173 kilometers. Keep in mind that actual flight times can vary depending on factors like layover duration, routing, and weather conditions.
Can you fly business or first class from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can fly business class or first class between JFK and MDW. You can fly business class with Frontier Airlines.First class cabins are available on Delta.
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, IL (MDW) from New York, NY (JFK)?
If you're planning to travel to Chicago from John F. Kennedy International Airport (JFK), you can fly directly into Midway International Airport (MDW). Some flights may connect through major hubs like Ronald Reagan Washington National (DCA), Hartsfield-Jackson Atlanta International (ATL), or Logan International (BOS) 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.
Airlines serving
Delta
Return price
£218
Distance
1166 km

Book with confidence

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 £218 and range up to £252.  

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 September, 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.  

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

Explore a world of travel with Expedia

*Available to Expedia members.