$89 Cheap Flights from New York (JFK) to Chicago (ORD)

View $89 flight on Sat, Aug 29, 2026Opens in a new window

Popular airlines from John F. Kennedy Intl. Airport (JFK) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from New York to Chicago (JFK-ORD)

Prices were available within the past 7 days and start at $89 for one-way flights and $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Jul 22 - Tue, Jul 28
JFK
New York
ORD
Chicago
$177 Roundtrip, found 1 hour ago
$177
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Jul 22 from New York to Chicago, returning Tue, Jul 28, priced at $177 found 1 hour ago
Delta
Fri, Jul 10 - Mon, Jul 13
JFK
New York
ORD
Chicago
$182 Roundtrip, just found
$182
Roundtrip
just found
Select Delta flight, departing Fri, Jul 10 from New York to Chicago, returning Mon, Jul 13, priced at $182 just found
American Airlines
Wed, Jun 10 - Wed, Jun 24
JFK
New York
ORD
Chicago
$187 Roundtrip, found 3 hours ago
$187
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Jun 10 from New York to Chicago, returning Wed, Jun 24, priced at $187 found 3 hours ago
JetBlue Airways
Thu, May 28 - Tue, Jun 9
JFK
New York
ORD
Chicago
$192 Roundtrip, found 5 hours ago
$192
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Thu, May 28 from New York to Chicago, returning Tue, Jun 9, priced at $192 found 5 hours ago
American Airlines
Tue, Dec 8 - Mon, Dec 14
JFK
New York
ORD
Chicago
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Dec 8 from New York to Chicago, returning Mon, Dec 14, priced at $197 found 1 hour ago
American Airlines
Tue, Jun 9 - Wed, Jun 10
JFK
New York
ORD
Chicago
$202 Roundtrip, just found
$202
Roundtrip
just found
Select American Airlines flight, departing Tue, Jun 9 from New York to Chicago, returning Wed, Jun 10, priced at $202 just found
JetBlue Airways
Fri, Jul 10 - Mon, Jul 13
JFK
New York
ORD
Chicago
$207 Roundtrip, just found
$207
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, Jul 10 from New York to Chicago, returning Mon, Jul 13, priced at $207 just found
American Airlines
Sat, Aug 22 - Tue, Sep 1
JFK
New York
ORD
Chicago
$209 Roundtrip, found 20 hours ago
$209
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Sat, Aug 22 from New York to Chicago, returning Tue, Sep 1, priced at $209 found 20 hours ago
Frontier Airlines
Tue, Jul 28 - Mon, Aug 10
JFK
New York
ORD
Chicago
$241 Roundtrip, found 1 day ago
$241
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jul 28 from New York to Chicago, returning Mon, Aug 10, priced at $241 found 1 day ago
Sun Country Airlines
Wed, Jul 29 - Thu, Aug 6
JFK
New York
ORD
Chicago
$383 Roundtrip, found 3 hours ago
$383
Roundtrip
found 3 hours ago
Select Sun Country Airlines flight, departing Wed, Jul 29 from New York to Chicago, returning Thu, Aug 6, priced at $383 found 3 hours ago

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $337
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $337

Frequently asked questions

How much does a flight from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $89 and cheap return flights from $177 New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $74 and $809, and return flights often range between $238 and $1282. 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 the cheapest fares first, and use the Price Tracking tool to receive alerts when New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
January is typically the cheapest month to fly from New York (JFK) to Chicago (ORD), with average return fares around $237. This is about 16% lower than the average price throughout the year, as January sees a drop in demand after the holiday season. Other cheap months to fly from New York to Chicago include February and September.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are 4 airlines offering direct flights from JFK to ORD:

  • Delta operates around 49 direct flights from JFK to ORD every week
  • American Airlines operates around 27 direct flights from JFK to ORD every week
  • JetBlue Airways operates around 14 direct flights from JFK to ORD every week
  • Frontier Airlines operates around 7 direct flights from JFK to ORD every week

What is the cheapest airline that flies from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
JetBlue Airways is one of the cheapest airlines offering connecting flights from New York (JFK) to Chicago (ORD) starting from around $312 for a round-trip ticket. 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.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare 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 airline to fly with from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from New York, NY (JFK) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, Delta offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. Delta offers the most daily flights from JFK to ORD, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
For flights from New York (JFK) to Chicago (ORD), January and February are the best months to travel. You can expect average return flight prices around $237 during these months, which is quite economical. These winter months see lower travel demand, meaning you can enjoy a more relaxed travel experience and potentially better deals.*Prices based on flights available on Expedia in the last year.
How many flights per day from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
On average, there are around 13 nonstop flights per day from John F. Kennedy Intl. (JFK) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from New York, NY (JFK) to Chicago, IL (ORD) typically departs at around 5:15 AM local time, operated by JetBlue Airways. This seasonal service is available in April, making it a great option if you're planning to travel during that month. An early departure helps you make the most of your day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from New York, NY (JFK) to Chicago, IL (ORD) are in the late morning, from 9am to 12pm. About 26% of passengers prefer this time window. Many major carriers, including American Airlines, Delta Air Lines, and United Airlines, offer flights during this window. This timing works well because it allows you to travel to Chicago after a productive morning in New York.
How long does it take to fly from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flying nonstop from JFK to ORD takes around 3 hours, with the route covering approximately 738 miles. Flights with a layover typically take 3 hours 30 minutes longer than direct options. 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 (ORD-O'Hare Intl.)?
First class seats are offered on the JFK to ORD route with American Airlines and Delta Air Lines.
How much is a business class flight from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from New York, NY (JFK) to Chicago, IL (ORD) typically costs between $754 - $1,117. A non-stop, one-way business class flight is usually around $402 - $535. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare 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)?
When traveling from John F. Kennedy Intl. (JFK) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). 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 (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare 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 (ORD-O'Hare Intl.) flight and hotel package?
Securing a New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages 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 (ORD-O'Hare Intl.)?
If you booked your New York, NY (JFK-John F. Kennedy Intl.) to Chicago, IL (ORD-O'Hare 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
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, JetBlue Airways, Sun Country Airlines
Roundtrip price
$177
Distance
737 mi
Average flight time
1 hour 55 mins

Book with confidence

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 July. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $89 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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