Discover affordable flights from New York to Chicago with prices starting from $240. Book your journey today!
New York
JFK
β
Chicago
ORD
10/28/2025 β 11/04/2025
Cheap flight deals from New York to Chicago
Average price start from:
i
$100
Round-trip flights from New York to Chicago starting at $100. Book now for the best deals!
One-way from:
i
$58
One-way flights from New York to Chicago starting at $58. Great for flexible travel!
Cheapest day:
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Tuesday
Tuesday is the cheapest day to fly from New York to Chicago. Save more by booking on this day!
Cheapest In:
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$148
Jun 2025
Jun 2025 is the cheapest month to fly from New York to Chicago with prices starting at $148.
Find flight deals from New York to Chicago
Cheapest flights from New York to Chicago
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Explore the cheapest oneway flights from New York to Chicago spotted daily.
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
ORD
Unknown City
$58
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
MDW
Unknown City
$58
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
ORD
Unknown City
$74
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
CVG
Unknown City
$80
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
ORD
Unknown City
$84
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
CVG
Unknown City
$89
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
IND
Unknown City
$92
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
AZO
Unknown City
$94
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
FWA
Unknown City
$101
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
CVG
Unknown City
$103
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
IND
Unknown City
$105
Non-stop β’ 60 min
JFK
New York
JFK - New York β’ 2025-10-28 β’ 09:00
Unknown
60 min
SDF
Unknown City
$105
Non-stop β’ 60 min
Price Trends & Analysis
Weekly Price Trends
Save money by choosing Tuesday flights to Chicago.
Monthly Price Trends
Best time to book flights from New York to Chicago is during August.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate, with cold winters averaging temperatures from 20Β°F to 30Β°F and hot summers ranging from 70Β°F to 90Β°F. The best times for comfortable travel are late spring (May) and early fall (September to October), when temperatures are mild and precipitation is generally lower.
Rainfall
The best time to visit Chicago is during late spring (May to early June) or early fall (September to October) when the weather is mild and pleasant. These seasons also feature vibrant local events like the Chicago Blues Festival and the Chicago Gourmet, allowing you to enjoy the city's culture without the summer tourist crowds.
Airlines at Chicago
Book your journey from New York to Chicago with leading airlines including Frontier Airlines, Jetblue Airways, Delta Air Lines, American Airlines. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from New York to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Places to Visit in Chicago
Chicago, the Windy City, dazzles with its stunning skyline, vibrant arts scene, and rich history. Explore the iconic Millennium Park, home to the reflective Cloud Gate, and immerse yourself in the compelling stories of the city's past at the Chicago History Museum. Visitors can savor deep-dish pizza, stroll along the picturesque Lake Michigan shoreline, and experience world-class performances at the renowned Lyric Opera, making every moment in this dynamic metropolis a celebration of culture and creativity.
About Chicago
Discover the beauty of Chicago when flying from New York. This captivating city combines rich heritage with contemporary charm, offering something special for every traveler. Plan your visit during off-peak periods for optimal savings and a more relaxed experience.
Airlines Flying from New York to Chicago
Book your journey from New York to Chicago with leading airlines including Frontier Airlines, Jetblue Airways, Delta Air Lines, American Airlines. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from New York to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Hotels in Chicago
For your visit to Chicago, choose hotels near ORD Airport for maximum convenience. Many accommodations offer complimentary airport shuttle services.
About Chicago
Discover the beauty of Chicago when flying from New York. This captivating city combines rich heritage with contemporary charm, offering something special for every traveler. Plan your visit during off-peak periods for optimal savings and a more relaxed experience.
Places to Visit in Chicago
Chicago, the Windy City, dazzles with its stunning skyline, vibrant arts scene, and rich history. Explore the iconic Millennium Park, home to the reflective Cloud Gate, and immerse yourself in the compelling stories of the city's past at the Chicago History Museum. Visitors can savor deep-dish pizza, stroll along the picturesque Lake Michigan shoreline, and experience world-class performances at the renowned Lyric Opera, making every moment in this dynamic metropolis a celebration of culture and creativity.
Hotels in Chicago
For your visit to Chicago, choose hotels near ORD Airport for maximum convenience. Many accommodations offer complimentary airport shuttle services.
Airlines Flying from New York to Chicago
Book your journey from New York to Chicago with leading airlines including Frontier Airlines, Jetblue Airways, Delta Air Lines, American Airlines. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from New York to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Frequently Asked Questions
What's the lowest price for flights from New York to Chicago?
You can find flights starting from $58. For better deals, book during August and choose Tuesday departures.
How long is the journey from New York to Chicago?
The average flight time is about 10-15 hours, with most routes including one stopover for better pricing and comfort.
What airlines operate flights on this route?
Several airlines serve this route including Frontier Airlines, Jetblue Airways, Delta Air Lines. Research current schedules and compare prices for the best deal.
How far in advance should I book?
For the best prices, book 2-3 months ahead and consider traveling during August when prices are typically lower.
What accommodation options are near ORD Airport?
ORD Airport has several nearby hotels with shuttle services, making it convenient for travelers with early or late flights.
What attractions can I visit in Chicago?
Chicago features a wonderful combination of historical sites and modern attractions. The best time to visit is during pleasant weather months for optimal sightseeing.
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