S$89 Cheap Flights from New York to Chicago

View S$89 flight on Sat, 13 Sep, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at S$89 for one-way flights and S$176 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 19 Aug - Wed, 20 Aug
JFK
New York
ORD
Chicago
S$176 Return, found 1 day ago
S$176
Return
found 1 day ago
Select Delta flight, departing Tue, 19 Aug from New York to Chicago, returning Wed, 20 Aug, priced at S$176 found 1 day ago
Delta
Tue, 19 Aug - Wed, 20 Aug
JFK
New York
ORD
Chicago
S$188 Return, found 1 day ago
S$188
Return
found 1 day ago
Select Delta flight, departing Tue, 19 Aug from New York to Chicago, returning Wed, 20 Aug, priced at S$188 found 1 day ago
JetBlue Airways
Mon, 4 Aug - Wed, 13 Aug
JFK
New York
ORD
Chicago
S$194 Return, found 21 hours ago
S$194
Return
found 21 hours ago
Select JetBlue Airways flight, departing Mon, 4 Aug from New York to Chicago, returning Wed, 13 Aug, priced at S$194 found 21 hours ago
Delta
Wed, 20 Aug - Sat, 6 Sep
JFK
New York
ORD
Chicago
S$195 Return, found 5 days ago
S$195
Return
found 5 days ago
Select Delta flight, departing Wed, 20 Aug from New York to Chicago, returning Sat, 6 Sep, priced at S$195 found 5 days ago
Delta
Tue, 19 Aug - Tue, 26 Aug
JFK
New York
ORD
Chicago
S$201 Return, found 4 days ago
S$201
Return
found 4 days ago
Select Delta flight, departing Tue, 19 Aug from New York to Chicago, returning Tue, 26 Aug, priced at S$201 found 4 days ago
JetBlue Airways
Mon, 4 Aug - Fri, 15 Aug
JFK
New York
ORD
Chicago
S$202 Return, found 21 hours ago
S$202
Return
found 21 hours ago
Select JetBlue Airways flight, departing Mon, 4 Aug from New York to Chicago, returning Fri, 15 Aug, priced at S$202 found 21 hours ago
Delta
Wed, 20 Aug - Thu, 21 Aug
JFK
New York
ORD
Chicago
S$208 Return, found 5 days ago
S$208
Return
found 5 days ago
Select Delta flight, departing Wed, 20 Aug from New York to Chicago, returning Thu, 21 Aug, priced at S$208 found 5 days ago
Delta
Fri, 5 Sep - Tue, 9 Sep
JFK
New York
ORD
Chicago
S$214 Return, found 1 day ago
S$214
Return
found 1 day ago
Select Delta flight, departing Fri, 5 Sep from New York to Chicago, returning Tue, 9 Sep, priced at S$214 found 1 day ago
Delta
Fri, 5 Sep - Tue, 9 Sep
JFK
New York
ORD
Chicago
S$227 Return, found 1 day ago
S$227
Return
found 1 day ago
Select Delta flight, departing Fri, 5 Sep from New York to Chicago, returning Tue, 9 Sep, priced at S$227 found 1 day ago
American Airlines
Fri, 5 Sep - Tue, 9 Sep
JFK
New York
ORD
Chicago
S$260 Return, found 1 day ago
S$260
Return
found 1 day ago
Select American Airlines flight, departing Fri, 5 Sep from New York to Chicago, returning Tue, 9 Sep, priced at S$260 found 1 day ago

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

September is typically the cheapest month to fly

From S$116 - S$211 per traveller.

Graph displaying average flight prices per month

New York to Chicago route information
Origin airport
John F. Kennedy Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways
Return price
S$176
Distance
1180 km
Average flight time
1 hour 56 mins

Perfect flights from New York to Chicago

Your Journey from New York to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from New York to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, JetBlue Airways, American Airlines. Our selection of flights from John F. Kennedy Intl. to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with New York to Chicago Flights

Experience the joy of finding cheap flights from John F. Kennedy Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$89 and roundtrip prices from S$176*.
 

Pre-Flight Essentials

Ensure a smooth journey from New York to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of Chicago. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your New York to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from New York to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from New York to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from New York to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from JFK Airport to ORD?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD) was S$176. Fares this cheap don't hang around, so make sure you book yours today. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from John F. Kennedy Intl. Airport (JFK) to O'Hare Airport?
Every air carrier has different terms and conditions. If you decide to cancel your trip, visit our Customer Service Portal.
How do I find cheap flights from JFK to O'Hare Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for John F. Kennedy Intl. Airport (JFK) to ORD flights, you'll see a "no change fees" filter for you to select.
How far is the flight from John F. Kennedy Intl. Airport (JFK) to O'Hare Airport?
The distance from JFK (JFK) to ORD (ORD) is just 1,200 kilometres. You'll be walking down the air bridge and picking up your baggage from the carousel before long.
Which airlines fly direct from JFK Airport to ORD?
With 121 flights every month operating from JFK to O'Hare Intl. Airport (ORD), Delta Air Lines (DL) is an excellent choice. You could also have a look at ticket prices with JetBlue Airways (B6). This airline operates 91 monthly flights between Jamaica and Chicago.
Are John F. Kennedy Intl. Airport (JFK) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to nab a fantastic last-minute deal from JFK Airport to ORD, but it's also possible to miss out altogether! As many airlines publish prices up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to book when you see a bargain. Expedia compares air carrier prices and updates flight deals all the time, so you can rest easy knowing you're always seeing the latest offers.

Explore a world of travel with Expedia

Chicago Airports

Chicago

New York Airports

New York

LaGuardia to Chicago
S$176.00

Newark Liberty Intl. Airport

Newark Liberty Intl. Airport to Chicago
S$220.30
*Available to Expedia members.