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

  • any
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • any
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • price
  • month of departure
  • month of return
$101
JetBlue outward: Dec 27, 2020
2:00a JFK » 4:46a ORD
JetBlue direct (2h46m)
United Airlines inbound: Dec 29, 2020
4:00p ORD » 6:03p LGA
United Airlines direct (2h03m)
$108
United Airlines outward: Nov 6, 2020
2:30p EWR » 1:44a ORD
United Airlines 1 stop (11h14m)
United Airlines inbound: Nov 8, 2020
4:00p ORD » 6:09p EWR
United Airlines direct (2h09m)
$115
United Airlines outward: Nov 20, 2020
11:00p LGA » 1:25a ORD
United Airlines direct (2h25m)
United Airlines inbound: Nov 23, 2020
1:00a ORD » 3:07a LGA
United Airlines direct (2h07m)
$157
Southwest Airlines outward: Nov 1, 2020
12:25p LGA » 2:45p MDW
Southwest Airlines direct (2h20m)
Delta Air Lines inbound: Nov 8, 2020
2:30p ORD » 4:31p LGA
Delta Air Lines direct (2h01m)
$162
United Airlines outward: Nov 24, 2020
4:00p EWR » 1:29a ORD
United Airlines 1 stop (9h29m)
American Airlines inbound: Dec 1, 2020
4:10p ORD » 7:55p JFK
American Airlines 1 stop (3h45m)
$202
Spirit Airlines outward: Nov 26, 2020
7:59p LGA » 6:29a ORD
Spirit Airlines 1 stop (10h30m)
United Airlines inbound: Nov 29, 2020
12:00p ORD » 4:03p LGA
United Airlines 1 stop (4h03m)
$202
Spirit Airlines outward: Nov 26, 2020
7:59p LGA » 6:29a ORD
Spirit Airlines 1 stop (10h30m)
United Airlines inbound: Nov 29, 2020
12:00p ORD » 4:03p LGA
United Airlines 1 stop (4h03m)
$210
Frontier Airlines outward: Nov 25, 2020
4:45p LGA » 12:38a ORD
Frontier Airlines 1 stop (7h53m)
United Airlines inbound: Nov 29, 2020
12:00p ORD » 4:03p LGA
United Airlines 1 stop (4h03m)
$216
United Airlines outward: Nov 25, 2020
2:20p EWR » 11:46p ORD
United Airlines 1 stop (9h26m)
Spirit Airlines inbound: Nov 26, 2020
4:59a ORD » 5:30p EWR
Spirit Airlines 1 stop (12h31m)
$217
Spirit Airlines outward: Nov 26, 2020
10:45p EWR » 6:13a ORD
Spirit Airlines 1 stop (7h28m)
United Airlines inbound: Nov 30, 2020
4:15a ORD » 6:17a EWR
United Airlines direct (2h02m)
$454
United Airlines outward: Dec 26, 2020
1:00p LGA » 3:24p ORD
United Airlines direct (2h24m)
United Airlines inbound: Dec 29, 2020
2:55p ORD » 5:11p EWR
United Airlines direct (2h16m)
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
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • all
  • Alaska Airlines
  • American Airlines
  • Frontier Airlines
  • JetBlue
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Nov 26, 2020
Spirit Airlines 1 stop
return: Nov 29, 2020
United Airlines direct
JetBlue
outbound: Nov 26, 2020
JetBlue 1 stop
return: Nov 29, 2020
JetBlue direct
American Airlines
outbound: Nov 26, 2020
American Airlines 2 stops
return: Nov 29, 2020
American Airlines 1 stop
United Airlines
outbound: Nov 20, 2020
United Airlines direct
return: Nov 22, 2020
United Airlines direct
Frontier Airlines
outbound: Nov 25, 2020
Frontier Airlines 1 stop
return: Nov 29, 2020
United Airlines 1 stop
Alaska Airlines
outbound: Dec 26, 2020
Alaska Airlines 1 stop
return: Dec 29, 2020
Alaska Airlines 1 stop

Travel tips for flights New York - Chicago

Information on Chicago
Route

Average flight duration: 2h02m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Oct 28, 2020 8:46 AM, GMT-5
  • Weather:
  • min. 41ºF, max. 49ºF
  • 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:
  • Oct 28, 2020 9:46 AM, GMT-4
  • Weather:
  • min. 51ºF, max. 57ºF

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.