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Find cheap one-way flights from New York to Chicago starting at US$26.

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to book flights from New York to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Cheapest airlines flights from New York to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines
From US$32
Southwest Airlines
From US$40
Frontier Airlines
From US$42
Delta Air Lines
From US$45
Sun Country Airlines
From US$93
Jetblue Airways
From US$103
American Airlines
From US$111
Breeze Airways
From US$125
United Airlines
From US$250
Porter Airlines
From US$384
ANA airlines

Find more flights and airlines

Find cheap flights from New York to Chicago by different airports

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from New York to Chicago.

  • Cheapest
    Spirit Airlines
    LGA
    20:03
    2h 40m
    Direct
    ORD
    21:43
    New York LaGuardia Airport - O'Hare International Airport
    Tue, Apr 16Spirit Airlines
    US$32
  • Southwest Airlines
    LGA
    06:30
    2h 25m
    Direct
    MDW
    07:55
    New York LaGuardia Airport - Midway International Airport
    Wed, Apr 10Southwest Airlines
    US$40
  • Spirit Airlines
    EWR
    16:30
    8h 1m
    1 transfer
    ORD
    23:31
    Newark Liberty International Airport - O'Hare International Airport
    Wed, Apr 24Spirit Airlines
    US$59
  • Spirit Airlines
    EWR
    16:30
    8h 1m
    1 transfer
    ORD
    23:31
    Newark Liberty International Airport - O'Hare International Airport
    Wed, Apr 24Spirit Airlines
    US$59
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from New York (NYC) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from New York to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much do flights from New York (NYC) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around $211.
  • How long does it take to fly from New York (NYC) to Chicago (CHI) and what is the distance?

    It takes around 2 hours 47 minutes to fly from New York (NYC) to Chicago (CHI).
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.
  • What are the most popular airlines that fly from New York (NYC) to Chicago (CHI)?

    Airlines with flights from New York (NYC) to Chicago (CHI): American Airlines, KLM, Air New Zealand, United Airlines, WestJet, Air Canada, Delta Air Lines and Spirit Airlines.

New York to Chicago Flight Information

Cheapest nonstop flight price

$26

Cheapest round-trip ticket price

$52

Off-season for travel

March

Peak season for travel

September

What You Should Know about Flights from New York to Chicago