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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  • May 2022
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  • month of departure
  • month of return
$193
United Airlines outward: May 25, 2022
1:48a EWR » 6:25a ORD
United Airlines 1 stop (4h37m)
United Airlines inbound: May 29, 2022
2:42a ORD » 4:59a EWR
United Airlines direct (2h17m)
$237
Delta Air Lines outward: Jun 4, 2022
12:05p EWR » 3:52p ORD
Delta Air Lines 1 stop (3h47m)
Unknown Company inbound: Jun 7, 2022
12:05p ORD » 8:25p SWF
Unknown Company 1 stop (8h20m)
$244
American Airlines outward: May 28, 2022
9:35p JFK » 12:16a ORD
American Airlines direct (2h41m)
Delta Air Lines inbound: Jun 4, 2022
2:05p ORD » 5:58p EWR
Delta Air Lines 1 stop (3h53m)
$262
United Airlines outward: Sep 1, 2022
12:00p EWR » 4:09p ORD
United Airlines 1 stop (4h09m)
United Airlines inbound: Sep 5, 2022
2:10p ORD » 6:26p EWR
United Airlines 1 stop (4h16m)
$292
JetBlue outward: Jul 13, 2022
2:30p LGA » 5:05p ORD
JetBlue direct (2h35m)
Allegiant Air inbound: Jul 18, 2022
2:22a MDW » 4:07p SWF
Allegiant Air 1 stop (13h45m)
$300
Spirit Airlines outward: Jul 1, 2022
12:59p LGA » 11:40p ORD
Spirit Airlines 1 stop (10h41m)
Spirit Airlines inbound: Jul 4, 2022
6:05p ORD » 11:45p LGA
Spirit Airlines 1 stop (5h40m)
$306
United Airlines outward: Jun 16, 2022
11:00a EWR » 1:25p ORD
United Airlines direct (2h25m)
Spirit Airlines inbound: Jun 20, 2022
12:50a ORD » 2:24p EWR
Spirit Airlines 1 stop (13h34m)
$322
Spirit Airlines outward: Jun 23, 2022
12:59p LGA » 11:40p ORD
Spirit Airlines 1 stop (10h41m)
Spirit Airlines inbound: Jun 27, 2022
6:05p ORD » 11:45p LGA
Spirit Airlines 1 stop (5h40m)
$378
Spirit Airlines outward: May 27, 2022
10:30p LGA » 6:36a ORD
Spirit Airlines 1 stop (8h06m)
American Airlines inbound: May 30, 2022
1:30p ORD » 3:34p LGA
American Airlines direct (2h04m)
Return
Departure
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Airlines operating flights from New York to Chicago

  • any
  • May 2022
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  • all
  • Alaska Airlines
  • American Airlines
  • JetBlue
  • Spirit Airlines
Spirit Airlines
outbound: Jun 4, 2022
Spirit Airlines 1 stop
return: Jun 7, 2022
Spirit Airlines 1 stop
JetBlue
outbound: Jul 13, 2022
JetBlue direct
return: Jul 17, 2022
Allegiant Air 1 stop
American Airlines
outbound: May 28, 2022
American Airlines direct
return: Jun 4, 2022
Delta Air Lines 1 stop
Alaska Airlines
outbound: Sep 1, 2022
Alaska Airlines 1 stop
return: Sep 5, 2022
Alaska Airlines 1 stop

Travel tips for flights New York - Chicago

Information on Chicago
Route

Average flight duration: 2h10m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • May 22, 2022 8:27 AM, GMT-5
  • Weather:
  • min. 50ºF, max. 59ºF
  • Departure city:
  • New York, USA
  • Airport(s):
  • La Guardia Airport (LGA)
  • Newark Liberty International Airport (EWR)
  • John F. Kennedy International Airport (JFK)
  • Westchester County Airport (HPN)
  • Long Island MacArthur Airport (ISP)
  • Local time:
  • May 22, 2022 9:27 AM, GMT-4
  • Weather:
  • min. 65ºF, max. 86ºF

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.