Flights to Chicago from New York - $38

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

Prices were available within the past 7 days and start at $38 for one-way flights and $77 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 31 - Wed, Jun 4

EWR

New York

ORD

Chicago

$77 Roundtrip, just found

$77

Roundtrip

just found

Select Spirit Airlines flight, departing Sat, May 31 from New York to Chicago, returning Wed, Jun 4, priced at $77 just found

Wed, Jun 4 - Sat, Jun 7

LGA

New York

ORD

Chicago

$110 Roundtrip, just found

$110

Roundtrip

just found

Select Spirit Airlines flight, departing Wed, Jun 4 from New York to Chicago, returning Sat, Jun 7, priced at $110 just found

Wed, May 28 - Wed, May 28

LGA

New York

MDW

Chicago

$137 Roundtrip, found 21 hours ago

$137

Roundtrip

found 21 hours ago

Select Southwest Airlines flight, departing Wed, May 28 from New York to Chicago, returning Wed, May 28, priced at $137 found 21 hours ago

Sun, May 25 - Wed, May 28

JFK

New York

ORD

Chicago

$137 Roundtrip, found 3 hours ago

$137

Roundtrip

found 3 hours ago

Select Delta flight, departing Sun, May 25 from New York to Chicago, returning Wed, May 28, priced at $137 found 3 hours ago

Sun, May 25 - Wed, May 28

JFK

New York

ORD

Chicago

$137 Roundtrip, found 3 hours ago

$137

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Sun, May 25 from New York to Chicago, returning Wed, May 28, priced at $137 found 3 hours ago

Sun, May 25 - Wed, May 28

EWR

New York

ORD

Chicago

$137 Roundtrip, found 1 hour ago

$137

Roundtrip

found 1 hour ago

Select United flight, departing Sun, May 25 from New York to Chicago, returning Wed, May 28, priced at $137 found 1 hour ago