Cheap flights from New York to Chicago

Travel > North America > United States > New York to Chicago flights

If you want to visit a vibrant, energetic city that's rich in heritage, culture, entertainment, and commerce, Chicago runs right up there with the big dogs. You could start by visiting downtown which is the center for government, finance, and commerce of Chicago and is encircled by The Loop, named for the elevated train tracks that loop around the central area. Tall skyscrapers such as the world's second-tallest building, the Sears Tower, and the Chicago Board of Trade are landmarks... (read more in our Chicago Travel Guide)

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Cheapest flights found for the next 6 months

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Check our newest flight offers to Chicago:

  • $298Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Buffalo, NY (BUF)Chicago, IL (MDW)12/16/202211:06 pm
    Chicago, IL (MDW)Buffalo, NY (BUF)12/31/202205:43 pm
    cheapoair.com check price
  • $418Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Buffalo, NY (BUF)Chicago, IL (MDW)01/02/202311:35 am
    Chicago, IL (MDW)Buffalo, NY (BUF)01/11/202310:26 pm
    cheapoair.com check price
  • $450Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    New York, NY (LGA)Chicago, IL (ORD)12/18/202209:29 am
    Chicago, IL (ORD)New York, NY (LGA)12/27/202209:50 am
    cheapoair.com check price
  • $468Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Buffalo, NY (BUF)Chicago, IL (MDW)12/11/202211:35 am
    Chicago, IL (MDW)Buffalo, NY (BUF)12/26/202205:21 pm
    cheapoair.com check price
  • $478Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Buffalo, NY (BUF)Chicago, IL (MDW)12/15/202211:35 am
    Chicago, IL (MDW)Buffalo, NY (BUF)12/30/202205:21 pm
    cheapoair.com check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesLos Angeles To Bridgetown Multiple Airlines airfares from Los Angeles in December
$2190 Depart: 12/31/2022
Return: 01/09/2023

provided by Cheapoair.com

Multiple AirlinesHouston To Kansas City Multiple Airlines airfares from Houston in September
$434 Depart: 09/01/2021
Return: 09/09/2021

provided by Cheapoair.com

LufthansaHouston To Naples Lufthansa airfares from Houston in December
$1506 Depart: 12/27/2022
Return: 01/11/2023

provided by Cheapoair.com

Spirit AirlinesDurham To Saint Thomas Spirit Airlines airfares from Durham in December
$479 Depart: 12/31/2022
Return: 01/12/2023

provided by Cheapoair.com

Oceanic AirlinesAtlanta To Lansing Oceanic Airlines airfares from Atlanta in August
$11554 Depart: 08/05/2020
Return: 08/25/2020

provided by FlyFar

Multiple AirlinesDenver To Fort Myers Multiple Airlines airfares from Denver in December
$592 Depart: 12/21/2022
Return: 12/30/2022

provided by Cheapoair.com

Jetblue AirwaysChicago To Niagara Falls Jetblue Airways airfares from Chicago in December
$244 Depart: 12/17/2020
Return: 12/27/2020

provided by Cheapoair.com

Jetblue AirwaysAlbany To Washington DC Jetblue Airways airfares from Albany in December
$1181 Depart: 12/11/2020
Return: 12/26/2020

provided by Cheapoair.com

Multiple AirlinesNewark To Bridgetown Multiple Airlines airfares from Newark in December
$3575 Depart: 12/28/2022
Return: 01/03/2023

provided by Cheapoair.com

 

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