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

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.

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.

Enter JFK to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

Frontier Airlines is one of the cheapest airlines offering connecting return flights from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (MDW-Midway Intl.), with tickets starting from around AU$217 for flights that can be booked for departure within the next year. These prices are for economy class tickets per adult. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

To find a cheap flight from New York, NY (JFK) to Chicago, IL (MDW), 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.

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.

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).

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.

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.

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.

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.

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.

It's easy to earn miles on a New York, NY (JFK) to Chicago, IL (MDW) 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.

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.

Typically, booking a last minute flight from New York, NY (JFK) to Chicago, IL (MDW) 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.

Securing a New York, NY (JFK) to Chicago, IL (MDW) 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.

If you booked your New York, NY (JFK) to Chicago, IL (MDW) 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.