Trip.com
>
Flights
>
Flights to United States
>
Flights to Illinois
>
Flights to Chicago
>
Flights from New York to Chicago

Find cheap 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.
American Airlines logo American Airlines Jetblue Airways logo Jetblue Airways

Cheap flight deals from New York to Chicago

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

  • Round-trip
  • One way

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

Flight Info | New York to Chicago

Cheapest one-way flight price AED 127
Cheapest return ticket price AED 304
Off-season for travel April
Peak season for travel June
Flight distance 1,145.24 km
Average flight time 2 hours 45 minutes
Popular airline American Airlines

When is the cheapest time to fly from New York to Chicago?

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

Cheapest flights
From price
Search
  • 15 22
  • 22 29

  • Jul

    29 6
  • 6 13
  • 13 20
  • 20 27

  • Aug

    27 3
  • 3 10
  • 10 17
  • 17 24
  • 24 31

  • Sep

    31 7
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

How to find a cheap flight from New York to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from New York to Chicago. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest New York to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for New York to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Thu, Jul 10 at AED 128 for one-way flights.
2
Compare cheap New York to Chicago flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from New York to Chicago. The cheapest airline operating is Spirit Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your New York to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap New York to Chicago flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from New York to Chicago to get exclusive deals for you.

More Travel Options

  • Top Routes from New York
  • Top Routes to Chicago
  • Trending Airlines