Cheap Flights from New York (NYC) to Chicago (CHI)

View AU$98 flight on Wed, 22 Oct. 2025Opens in a new window

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Cheap Flights from New York (NYC) to Chicago (CHI)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, 2 Sep. - Thu, 4 Sep.
LGA
New York
ORD
Chicago
AU$211 Return, found 5 days ago
AU$211
Return
found 5 days ago
Select American Airlines flight, departing Tue, 2 Sep. from New York to Chicago, returning Thu, 4 Sep., priced at AU$211 found 5 days ago
Delta
Tue, 2 Sep. - Thu, 4 Sep.
LGA
New York
ORD
Chicago
AU$211 Return, found 5 days ago
AU$211
Return
found 5 days ago
Select Delta flight, departing Tue, 2 Sep. from New York to Chicago, returning Thu, 4 Sep., priced at AU$211 found 5 days ago
American Airlines
Tue, 2 Sep. - Thu, 4 Sep.
EWR
New York
ORD
Chicago
AU$211 Return, found 5 days ago
AU$211
Return
found 5 days ago
Select American Airlines flight, departing Tue, 2 Sep. from New York to Chicago, returning Thu, 4 Sep., priced at AU$211 found 5 days ago
Delta
Thu, 4 Sep. - Fri, 5 Sep.
LGA
New York
ORD
Chicago
AU$211 Return, found 1 day ago
AU$211
Return
found 1 day ago
Select Delta flight, departing Thu, 4 Sep. from New York to Chicago, returning Fri, 5 Sep., priced at AU$211 found 1 day ago
Delta
Thu, 16 Oct. - Mon, 20 Oct.
JFK
New York
ORD
Chicago
AU$212 Return, found 3 hours ago
AU$212
Return
found 3 hours ago
Select Delta flight, departing Thu, 16 Oct. from New York to Chicago, returning Mon, 20 Oct., priced at AU$212 found 3 hours ago
American Airlines
Thu, 4 Sep. - Sat, 13 Sep.
LGA
New York
ORD
Chicago
AU$226 Return, found 2 days ago
AU$226
Return
found 2 days ago
Select American Airlines flight, departing Thu, 4 Sep. from New York to Chicago, returning Sat, 13 Sep., priced at AU$226 found 2 days ago
American Airlines
Wed, 3 Dec. - Mon, 8 Dec.
JFK
New York
ORD
Chicago
AU$227 Return, found 5 days ago
AU$227
Return
found 5 days ago
Select American Airlines flight, departing Wed, 3 Dec. from New York to Chicago, returning Mon, 8 Dec., priced at AU$227 found 5 days ago
United
Thu, 4 Sep. - Mon, 22 Sep.
EWR
New York
ORD
Chicago
AU$304 Return, found 16 hours ago
AU$304
Return
found 16 hours ago
Select United flight, departing Thu, 4 Sep. from New York to Chicago, returning Mon, 22 Sep., priced at AU$304 found 16 hours ago
JetBlue Airways
Tue, 2 Dec. - Sun, 14 Dec.
JFK
New York
ORD
Chicago
AU$335 Return, found 5 days ago
AU$335
Return
found 5 days ago
Select JetBlue Airways flight, departing Tue, 2 Dec. from New York to Chicago, returning Sun, 14 Dec., priced at AU$335 found 5 days ago
Alaska Airlines
Thu, 30 Oct. - Wed, 5 Nov.
EWR
New York
ORD
Chicago
AU$569 Return, found 20 hours ago
AU$569
Return
found 20 hours ago
Select Alaska Airlines flight, departing Thu, 30 Oct. from New York to Chicago, returning Wed, 5 Nov., priced at AU$569 found 20 hours ago

Find the cheapest month to fly from New York (NYC) to Chicago (CHI)

March is typically the cheapest month to fly

From AU$87 - AU$435 per traveller.

Graph displaying average flight prices per month

Flight from New York to Chicago route information
Origin airport
LaGuardia
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, United
Return price
AU$210
Distance
1170 km

NYC to CHI Flights

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Chicago Flight Deals

Chicago

New York to O'Hare Intl.
AU$210.40
New York to Midway Intl.
AU$241.70

Milwaukee

New York Airports

New York

LaGuardia to Chicago
AU$210.40
John F. Kennedy Intl. to Chicago
AU$211.70

Newark Liberty Intl. Airport

Newark Liberty Intl. Airport to Chicago
AU$210.40
*Available to Expedia members.