Take off on cheap flights from New York to Chicago, your adventure starts now!

Find cheap airline tickets from New York to Chicago by date

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  • September 2021
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  • any
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  • price
  • month of departure
  • month of return
$78
Spirit Airlines outward: Oct 3, 2021
11:20a EWR » 6:44p ORD
Spirit Airlines 1 stop (7h24m)
Spirit Airlines inbound: Oct 7, 2021
2:45p ORD » 12:12a EWR
Spirit Airlines 1 stop (9h27m)
$80
Spirit Airlines outward: Oct 3, 2021
11:20a EWR » 6:44p ORD
Spirit Airlines 1 stop (7h24m)
Spirit Airlines inbound: Oct 7, 2021
2:45p ORD » 12:12a EWR
Spirit Airlines 1 stop (9h27m)
$91
Spirit Airlines outward: Nov 18, 2021
2:15a EWR » 4:02p ORD
Spirit Airlines 1 stop (13h47m)
Spirit Airlines inbound: Nov 19, 2021
2:00p ORD » 2:34a LGA
Spirit Airlines 1 stop (12h34m)
$92
Spirit Airlines outward: Dec 4, 2021
2:15a EWR » 4:00p ORD
Spirit Airlines 1 stop (13h45m)
Spirit Airlines inbound: Dec 7, 2021
12:52p ORD » 9:14p EWR
Spirit Airlines 1 stop (8h22m)
$162
United Airlines outward: May 12, 2022
3:00p LGA » 5:29p ORD
United Airlines direct (2h29m)
American Airlines inbound: May 15, 2022
1:55p ORD » 4:00p EWR
American Airlines direct (2h05m)
$231
Spirit Airlines outward: Nov 25, 2021
5:39p EWR » 1:45a ORD
Spirit Airlines 1 stop (8h06m)
American Airlines inbound: Nov 29, 2021
3:10a ORD » 1:26p LGA
American Airlines 1 stop (10h16m)
Return
Departure
Choose when you'd like to depart to Chicago (USA):
Find the cheapest New York Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for New York - Chicago with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from New York to Chicago

  • any
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • April 2022
  • May 2022
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  • all
  • American Airlines
  • JetBlue
  • United Airlines
JetBlue
outbound: May 12, 2022
JetBlue direct
return: May 15, 2022
JetBlue direct
United Airlines
outbound: May 12, 2022
United Airlines direct
return: May 15, 2022
American Airlines direct
American Airlines
outbound: Dec 3, 2021
American Airlines direct
return: Dec 7, 2021
American Airlines direct

Travel tips for flights New York - Chicago

Information on Chicago
Route

Average flight duration: 8h25m (flight with stopovers)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Sep 27, 2021 7:47 PM, GMT-5
  • Weather:
  • min. 62ºF, max. 76ºF
  • Departure city:
  • New York, USA
  • Airport(s):
  • LaGuardia Airport (LGA)
  • Newark Liberty International Airport (EWR)
  • John F. Kennedy International Airport (JFK)
  • Westchester County Airport (HPN)
  • Long Island MacArthur Airport (ISP)
  • Local time:
  • Sep 27, 2021 8:47 PM, GMT-4
  • Weather:
  • min. 59ºF, max. 75ºF

Why travel by plane from New York to Chicago?

With around 800 miles between New York and Chicago, a drive from city to city would take approximately 12h 10m. By choosing to fly, travelers can shave around 9h 30m off their travel time, as a flight between the two cities takes just 2h 40m. Passengers will arrive into O'Hare International Airport, from which the CTA Blue Line 'L' train will transport travelers into the city center quickly and efficiently.

What is there to see and do in Chicago?

Bordering Lake Michigan, Chicago is filled with museums, restaurants, attractions and more. One of the largest cities in the US, The Windy City is home to a population of over 2 million. Visit Millennium Park and admire its famous Cloud Gate sculpture (also known as The Bean); catch a baseball game at Wrigley Field; or explore one of the city's many museums such as the Art Institute of Chicago or The Field Museum. Taking a ride up to the top of the 360 Chicago is a must for stunning panoramic views over the city, while a walk along the Chicago Riverwalk allows visitors to admire beautiful architecture and relax in a riverside café.