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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  • month of departure
  • month of return
$114
United Airlines outward: Oct 25, 2023
12:30p LGA » 3:01p ORD
United Airlines direct (2h31m)
United Airlines inbound: Oct 28, 2023
1:05p ORD » 3:15p EWR
United Airlines direct (2h10m)
$119
United Airlines outward: Oct 18, 2023
8:15p LGA » 10:50p ORD
United Airlines direct (2h35m)
Spirit Airlines inbound: Oct 20, 2023
1:08a ORD » 8:04p LGA
Spirit Airlines 1 stop (18h56m)
$119
Unknown Company outward: Oct 28, 2023
4:14a EWR » 2:52p ORD
Unknown Company 1 stop (10h38m)
Spirit Airlines inbound: Nov 5, 2023
12:00p ORD » 2:11p LGA
Spirit Airlines direct (2h11m)
$130
Unknown Company outward: Sep 30, 2023
1:58a LGA » 12:55a MDW
Unknown Company 1 stop (22h57m)
Frontier Airlines inbound: Oct 3, 2023
1:38a ORD » 11:00p LGA
Frontier Airlines 1 stop (21h22m)
$137
Spirit Airlines outward: Oct 19, 2023
2:50p LGA » 12:13a ORD
Spirit Airlines 1 stop (9h23m)
Unknown Company inbound: Oct 21, 2023
4:07a ORD » 1:51p LGA
Unknown Company 1 stop (9h44m)
$141
Unknown Company outward: Sep 30, 2023
1:58a LGA » 12:38a ORD
Unknown Company 1 stop (22h40m)
Unknown Company inbound: Oct 1, 2023
11:48p MDW » 1:51p LGA
Unknown Company 1 stop (14h03m)
$142
Unknown Company outward: Sep 30, 2023
1:58a LGA » 12:55a MDW
Unknown Company 1 stop (22h57m)
Unknown Company inbound: Oct 2, 2023
12:24a ORD » 1:51p LGA
Unknown Company 1 stop (13h27m)
$149
Unknown Company outward: Oct 21, 2023
4:14a EWR » 2:42p ORD
Unknown Company 1 stop (10h28m)
Unknown Company inbound: Oct 22, 2023
12:10p MDW » 2:20p EWR
Unknown Company 1 stop (26h10m)
$152
Frontier Airlines outward: Oct 7, 2023
4:50a LGA » 6:07a MDW
Frontier Airlines 1 stop (25h17m)
Frontier Airlines inbound: Oct 8, 2023
3:43p MDW » 11:08p LGA
Frontier Airlines 1 stop (7h25m)
Return
Departure
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Airlines operating flights from New York to Chicago

  • any
  • September 2023
  • October 2023
  • November 2023
  • December 2023
  • January 2024
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  • April 2024
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  • all
  • Delta Air Lines
  • Frontier Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Sep 29, 2023
Spirit Airlines 1 stop
return: Oct 2, 2023
Frontier Airlines 1 stop
United Airlines
outbound: Oct 18, 2023
United Airlines direct
return: Oct 19, 2023
Spirit Airlines 1 stop
Delta Air Lines
outbound: Oct 18, 2023
Delta Air Lines direct
return: Oct 19, 2023
Delta Air Lines direct
Frontier Airlines
outbound: Oct 25, 2023
Frontier Airlines 1 stop
return: Oct 28, 2023
Spirit Airlines 1 stop

Travel tips for flights New York - Chicago

Information on Chicago
Route

Average flight duration: 19h34m (flight with stopovers)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Sep 23, 2023 10:11 PM, GMT-5
  • Weather:
  • min. 61ºF, max. 75ºF
  • Departure city:
  • New York, USA
  • Airport(s):
  • LaGuardia International 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 23, 2023 11:11 PM, GMT-4
  • Weather:
  • min. 57ºF, max. 69ºF

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.