Cheap Flights from New York to Chicago
Find flight deals from New York to Chicago
Compare prices, find the best time to fly, and save money.
Round-trip from
$563
American Airlines
2 stops
New York to Chicago
One-way from
$352
Delta Air Lines
Nonstop
New York to Chicago
Popular in
December
Highest demand for flights based on searches. Prices may increase by up to 15%.
Cheapest in
Jun
Lowest prices on average. 15% potential savings. best time to book.
What is the cheapest month to fly?
Currently, Jun is the cheapest month to book a flight from New York to Chicago. Prices can fluctuate, so booking in advance is recommended.
What is the cheapest day to fly?
Travelers seeking maximum savings should consider departing on weekdays. Monday often offers the lowest fares.
Best time of day to fly?
Flying early in the morning can often save you money compared to midday flights.
Flight Schedule: New York to Chicago
| Airline | Departure | Arrival | Duration |
|---|---|---|---|
| American Airlines | 08:00 AM | 01:30 PM | 4h 00m |
| Delta Air Lines | 02:15 PM | 07:45 PM | 4h 30m |
| United Airlines | 10:30 PM | 03:00 AM (+1) | 5h 00m |
Stopover Options
Cheapest Stopover
Muscat (MCT)
Flights with a stop here start from $316.
Most Popular Stopover
Bahrain (BAH)
Travelers often choose to connect through Bahrain (BAH).
Airlines Flying This Route
Return Flight: Chicago to New York
Planning your return trip? Flights from Chicago to New York are also available with competitive pricing. It's often cheaper to book a round-trip ticket, but if you need flexibility, one-way fares are a great option.
Chicago to New York FlightsFrequently Asked Questions
How long is the flight from New York to Chicago?
The average flight time is approximately 3h 3 m, though this varies based on wind speeds and the specific flight path utilized by the airline.
What is the best price for this route?
Our data shows that Jun is typically the cheapest month to fly this route, with prices starting from $352. Booking 30-60 days in advance often yields the best savings.
Are there direct flights available?
Yes, there are typically direct flights available for this route daily. However, connecting flights with stops in major hubs like Dubai or Doha may sometimes offer better value.
What are the baggage allowance policies?
Most international airlines on this route offer 23-30kg of checked baggage for Economy class. Low-cost carriers may charge extra for checked bags, so always verify before booking.
Do I need a visa for travel?
Visa requirements depend on your nationality. Travelers should check with the embassy of Chicago for specific entry requirements before their trip.
What time of day is cheapest to fly?
Early morning flights (before 8 AM) are often less expensive than flights during peak daytime hours. Red-eye flights can also offer significant discounts.
Can I cancel or change my flight?
Cancellation policies vary by airline and ticket class. Basic Economy tickets are often non-refundable, while Standard or Flex tickets allow changes for a fee. Check the specific fare rules during checkout.
Trending from UAE
Popular from Dubai (DXB)
Popular from Sharjah (SHJ)
Popular from New York
Flights to Chicago
Explore Cheap Holidays in Chicago
Complete your trip with our best-value holiday packages.
Top Tours & Activities in Chicago
Discover the best experiences and adventures near you.
San Marino Nature & Adventure Tour
Discover the natural beauty of San Marino through hiking, wildlife viewing, and outdoor adventures in stunning landscapes.
From
AED 899
Cabo Verde 2-Day Adventure Package
Experience the best of Cabo Verde over two days with accommodation, meals, and a comprehensive itinerary of top attractions.
From
AED 849
North Macedonia 2-Day Adventure Package
Experience the best of North Macedonia over two days with accommodation, meals, and a comprehensive itinerary of top attractions.
From
AED 1274
São Tomé and Príncipe Food & Culinary Tour
Taste authentic São Tomé and Príncipe cuisine through street food tours, market visits, and traditional cooking experiences.
From
AED 329
Gabon Cultural Heritage Experience
Immerse yourself in the rich cultural heritage of Gabon through traditional villages, historical sites, and local customs.
From
AED 449
Cabo Verde Sunset & Photography Tour
Capture stunning sunset views at Cabo Verde's most scenic locations with professional photography guidance.
From
AED 284
Nepal 2-Day Adventure Package
Experience the best of Nepal over two days with accommodation, meals, and a comprehensive itinerary of top attractions.
From
AED 764
Moldova Cultural Heritage Experience
Immerse yourself in the rich cultural heritage of Moldova through traditional villages, historical sites, and local customs.
From
AED 599
