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

Popular airlines from John F. Kennedy Intl. Airport (JFK) to Chicago, IL (PWK-Chicago Executive)

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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 center is 23 minutes. Flights from $76
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $76
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $291
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $291

Frequently asked questions

How much does a flight from John F. Kennedy Intl. Airport (JFK) to Chicago Executive Airport (PWK) cost?
Grab a cheap one-way flight or cheap return flight from John F. Kennedy Intl. Airport (JFK) to Chicago Executive Airport (PWK) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from John F. Kennedy Intl. Airport (JFK) to Chicago Executive Airport (PWK)?
is the most affordable month to fly from JFK to PWK. Planning your trip for the off-season is often the key to better flight prices.
What is the cheapest airline that flies from John F. Kennedy Intl. Airport (JFK) to Chicago Executive Airport (PWK)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from JFK to PWK. Then, sort your results by "Price (lowest to highest)" to pick up a great deal.
How many flights per day from John F. Kennedy Intl. Airport (JFK) to Chicago Executive Airport (PWK)?
There aren't any daily nonstop flights departing from John F. Kennedy Intl. Airport (JFK) to Chicago Executive Airport (PWK). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way in no time.
What day of the week has the most flights from JFK to PWK?
Generally you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* But this can change based on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from John F. Kennedy Intl. Airport (JFK) to Chicago Executive Airport (PWK)?
To arrive at Chicago Executive Airport (PWK) without delays, book a flight that takes off from John F. Kennedy Intl. Airport (JFK) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from John F. Kennedy Intl. Airport (JFK)?
Browse your flight options from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD). This is the only Chicago airport you can arrive at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from John F. Kennedy Intl. Airport (JFK) to Chicago Executive Airport (PWK) last-minute?
Waiting until right before your break to book your flight from JFK to PWK often results in higher prices. Although you may find some last-minute deals, there's no guarantee. Allow some flexibility in your schedule to boost your chances of snagging a bargain.
Is it cheaper to book a JFK to PWK flight and hotel package?
Booking a JFK to PWK flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Select from our impressive 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 John F. Kennedy Intl. Airport (JFK) to Chicago Executive Airport (PWK)?
If you booked your JFK to PWK flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for further details.

Travel information

Origin airport
John F. Kennedy Intl.
Destination airport
Chicago Executive
Distance
737 mi

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New York to Chicago Flights

The cheapest times to fly from New York to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from New York to Chicago are during the month of . You can find some of the cheapest flights from New York to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from New York to Chicago

Sunday is one of the best days to book for cheap flights from New York to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from New York to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from New York to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap New York to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your New York to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

New York to Chicago Flights

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*Available to One Key members.