S$95 Cheap Flights from New York to Chicago

View S$95 flight on Tue, 2 Dec, 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 S$95 for one-way flights and S$211 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 30 Oct - Wed, 5 Nov
JFK
New York
ORD
Chicago
S$211 Return, found 1 day ago
S$211
Return
found 1 day ago
Select Delta flight, departing Thu, 30 Oct from New York to Chicago, returning Wed, 5 Nov, priced at S$211 found 1 day ago
Delta
Thu, 11 Sep - Tue, 16 Sep
JFK
New York
ORD
Chicago
S$228 Return, found 1 day ago
S$228
Return
found 1 day ago
Select Delta flight, departing Thu, 11 Sep from New York to Chicago, returning Tue, 16 Sep, priced at S$228 found 1 day ago
Delta
Thu, 30 Oct - Wed, 5 Nov
JFK
New York
ORD
Chicago
S$229 Return, found 1 day ago
S$229
Return
found 1 day ago
Select Delta flight, departing Thu, 30 Oct from New York to Chicago, returning Wed, 5 Nov, priced at S$229 found 1 day ago
Delta
Sat, 27 Sep - Mon, 29 Sep
JFK
New York
ORD
Chicago
S$237 Return, found 1 day ago
S$237
Return
found 1 day ago
Select Delta flight, departing Sat, 27 Sep from New York to Chicago, returning Mon, 29 Sep, priced at S$237 found 1 day ago
Delta
Mon, 23 Feb - Mon, 2 Mar
JFK
New York
ORD
Chicago
S$241 Return, found 3 days ago
S$241
Return
found 3 days ago
Select Delta flight, departing Mon, 23 Feb from New York to Chicago, returning Mon, 2 Mar, priced at S$241 found 3 days ago
Delta
Sat, 27 Sep - Mon, 29 Sep
JFK
New York
ORD
Chicago
S$255 Return, found 1 day ago
S$255
Return
found 1 day ago
Select Delta flight, departing Sat, 27 Sep from New York to Chicago, returning Mon, 29 Sep, priced at S$255 found 1 day ago
American Airlines
Thu, 30 Oct - Wed, 5 Nov
JFK
New York
ORD
Chicago
S$256 Return, found 1 day ago
S$256
Return
found 1 day ago
Select American Airlines flight, departing Thu, 30 Oct from New York to Chicago, returning Wed, 5 Nov, priced at S$256 found 1 day ago
Delta
Sat, 13 Sep - Tue, 16 Sep
JFK
New York
ORD
Chicago
S$260 Return, found 2 days ago
S$260
Return
found 2 days ago
Select Delta flight, departing Sat, 13 Sep from New York to Chicago, returning Tue, 16 Sep, priced at S$260 found 2 days ago
Delta
Thu, 11 Sep - Tue, 16 Sep
JFK
New York
ORD
Chicago
S$266 Return, found 1 day ago
S$266
Return
found 1 day ago
Select Delta flight, departing Thu, 11 Sep from New York to Chicago, returning Tue, 16 Sep, priced at S$266 found 1 day ago
Delta
Thu, 30 Oct - Wed, 5 Nov
JFK
New York
ORD
Chicago
S$269 Return, found 1 day ago
S$269
Return
found 1 day ago
Select Delta flight, departing Thu, 30 Oct from New York to Chicago, returning Wed, 5 Nov, priced at S$269 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 S$113 - S$249 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
Return price
S$210
Distance
1180 km
Average flight time
1 hour 54 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, 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$95 and roundtrip prices from S$211*.
 

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 . 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$211. 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

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S$179.20

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S$240.70
*Available to Expedia members.