$29 Cheap Flights from New York (JFK) to Chicago (ORD)

View $29 flight on Wed, Nov 12, 2025Opens 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 $29 for one-way flights and $55 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Nov 12 - Wed, Nov 19
JFK
New York
ORD
Chicago
$55 Roundtrip, found 8 hours ago
$55
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Nov 12 from New York to Chicago, returning Wed, Nov 19, priced at $55 found 8 hours ago
Frontier Airlines
Mon, Nov 10 - Wed, Nov 12
JFK
New York
ORD
Chicago
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Nov 10 from New York to Chicago, returning Wed, Nov 12, priced at $56 just found
Frontier Airlines
Thu, Nov 13 - Sat, Nov 15
JFK
New York
ORD
Chicago
$60 Roundtrip, just found
$60
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Nov 13 from New York to Chicago, returning Sat, Nov 15, priced at $60 just found
Frontier Airlines
Fri, Feb 27 - Sun, Mar 1
JFK
New York
ORD
Chicago
$64 Roundtrip, found 1 hour ago
$64
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Feb 27 from New York to Chicago, returning Sun, Mar 1, priced at $64 found 1 hour ago
Frontier Airlines
Wed, Nov 12 - Tue, Nov 18
JFK
New York
ORD
Chicago
$65 Roundtrip, found 3 hours ago
$65
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Nov 12 from New York to Chicago, returning Tue, Nov 18, priced at $65 found 3 hours ago
Frontier Airlines
Wed, Nov 12 - Fri, Nov 14
JFK
New York
ORD
Chicago
$66 Roundtrip, just found
$66
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Nov 12 from New York to Chicago, returning Fri, Nov 14, priced at $66 just found
American Airlines
Thu, Nov 13 - Mon, Nov 17
JFK
New York
ORD
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select American Airlines flight, departing Thu, Nov 13 from New York to Chicago, returning Mon, Nov 17, priced at $137 just found
JetBlue Airways
Sat, Nov 15 - Tue, Nov 18
JFK
New York
ORD
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Nov 15 from New York to Chicago, returning Tue, Nov 18, priced at $137 just found
Delta
Sat, Nov 15 - Mon, Nov 17
JFK
New York
ORD
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Delta flight, departing Sat, Nov 15 from New York to Chicago, returning Mon, Nov 17, priced at $137 just found
Sun Country Airlines
Thu, Apr 9 - Sun, Apr 12
JFK
New York
ORD
Chicago
$292 Roundtrip, found 1 day ago
$292
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Thu, Apr 9 from New York to Chicago, returning Sun, Apr 12, priced at $292 found 1 day ago

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

October is typically the cheapest month to fly

From $88 - $276 per traveler.

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 $173
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $173
Flights from New York (JFK) to Chicago (ORD)
Origin airport
John F. Kennedy Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Sun Country Airlines
Roundtrip price
$55
Distance
737 mi
Average flight time
1 hour 48 mins

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 November. 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 $29 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.

 

Frequently asked questions

How much does a flight from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight from $29 or cheap return flight from $55 from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from JFK to ORD is November, when demand is low. Off-peak months are usually when better flight deals are available between these airports.
Which airlines fly direct from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD)?
Avoid the detours and travel nonstop to O'Hare Intl. Airport (ORD) from John F. Kennedy Intl. Airport (JFK) with 3 airlines, including:

  • Delta Air Lines
  • American Airlines
  • JetBlue Airways

What is the cheapest airline that flies from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD)?
While prices may vary depending on your travel dates, JetBlue Airways and American Airlines are popular options for flights between John F. Kennedy Intl. Airport (JFK) and O'Hare Intl. Airport (ORD). You can also compare carriers on Expedia and use the "Sort by" filter to find the cheapest ticket for your JFK to ORD flight.
How many flights per day from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD)?
Each day on average, 6 direct flights take off from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD). Pick the departure time that best suits your plans.
What are the most popular departure times for flights from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD)?
More travelers fly between JFK and ORD at 3 PM than at any other time of day. Prefer a quieter experience? Pick a flight outside the busiest times and there's a chance you'll save on your fare as well.
What day of the week has the most flights from JFK to ORD?
Fly on a Friday if you're after the largest selection of flights from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD).
What is the earliest flight from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD)?
John F. Kennedy Intl. Airport (JFK)'s first flight to O'Hare Intl. Airport (ORD) is at approximately 8:00AM UTC-5. With a total flight time of 2h 55m, you'll land at around 9:55AM UTC-6.
How long does it take to fly from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD)?
Flights from JFK to ORD have an average travel time of 2 hours and 51 minutes. The distance between the two is 740 mi.
What airline has the least delays from JFK to ORD?
With 100% of flights usually arriving as scheduled, Alaska Airlines has the best on-time performance for direct flights from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD). To keep track of your flight status and get notified if anything changes, use the Expedia App.
What is the best time to fly from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD) route, aim to travel before 3 PM. Later flights have a 22% higher chance of being canceled.**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)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from John F. Kennedy Intl. Airport (JFK). Check out the available options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until right before your break to book your flight from JFK to ORD generally means paying more. While you may find some last-minute offers, they're not always guaranteed. Keep your travel schedule open for a better chance of getting a bargain.
Is it cheaper to book a JFK to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a JFK to ORD flight and hotel package with Expedia could lead to significant savings. Better still, having it all in one place will take the stress out of travel planning. Simply pick your flights and choose from our wide range of hotels, then personalize your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD)?
Usually, it's possible to cancel or reschedule your JFK to ORD flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

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