Flights from New York to Chicago

Cheapest flights from New York

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, May 29 - Wed, Jun 5

LGA

LaGuardia

ORD

O'Hare Intl.

$71 Roundtrip, found 8 hours ago

$71

Roundtrip

found 8 hours ago

Select Spirit Airlines flight, departing Wed, May 29 from LaGuardia to O'Hare Intl., returning Wed, Jun 5, priced at $71 found 8 hours ago

Sat, May 11 - Wed, May 15

LGA

LaGuardia

ORD

O'Hare Intl.

$85 Roundtrip, found 1 day ago

$85

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, May 11 from LaGuardia to O'Hare Intl., returning Wed, May 15, priced at $85 found 1 day ago

Thu, May 2 - Tue, May 7

LGA

LaGuardia

ORD

O'Hare Intl.

$90 Roundtrip, found 5 days ago

$90

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Thu, May 2 from LaGuardia to O'Hare Intl., returning Tue, May 7, priced at $90 found 5 days ago

Tue, May 21 - Wed, May 29

LGA

LaGuardia

ORD

O'Hare Intl.

$96 Roundtrip, found 3 days ago

$96

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Tue, May 21 from LaGuardia to O'Hare Intl., returning Wed, May 29, priced at $96 found 3 days ago

Wed, May 1 - Wed, May 8

LGA

LaGuardia

MDW

Midway Intl.

$96 Roundtrip, found 5 days ago

$96

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, May 1 from LaGuardia to Midway Intl., returning Wed, May 8, priced at $96 found 5 days ago

Sat, May 11 - Tue, May 14

LGA

LaGuardia

ORD

O'Hare Intl.

$99 Roundtrip, found 1 day ago

$99

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, May 11 from LaGuardia to O'Hare Intl., returning Tue, May 14, priced at $99 found 1 day ago

Mon, May 6 - Wed, May 8

LGA

LaGuardia

MDW

Midway Intl.

$102 Roundtrip, found 5 days ago

$102

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Mon, May 6 from LaGuardia to Midway Intl., returning Wed, May 8, priced at $102 found 5 days ago

Wed, May 29 - Wed, Jun 5

LGA

LaGuardia

ORD

O'Hare Intl.

$105 Roundtrip, found 8 hours ago

$105

Roundtrip

found 8 hours ago

Select Delta flight, departing Wed, May 29 from LaGuardia to O'Hare Intl., returning Wed, Jun 5, priced at $105 found 8 hours ago

Wed, May 29 - Wed, Jun 5

LGA

LaGuardia

ORD

O'Hare Intl.

$107 Roundtrip, found 8 hours ago

$107

Roundtrip

found 8 hours ago

Select Frontier Airlines flight, departing Wed, May 29 from LaGuardia to O'Hare Intl., returning Wed, Jun 5, priced at $107 found 8 hours ago

Tue, May 21 - Tue, May 28

LGA

LaGuardia

ORD

O'Hare Intl.

$110 Roundtrip, found 5 days ago

$110

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, May 21 from LaGuardia to O'Hare Intl., returning Tue, May 28, priced at $110 found 5 days ago

Wed, May 1 - Fri, May 3

LGA

LaGuardia

MDW

Midway Intl.

$112 Roundtrip, found 5 days ago

$112

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, May 1 from LaGuardia to Midway Intl., returning Fri, May 3, priced at $112 found 5 days ago

Wed, May 8 - Mon, May 13

LGA

LaGuardia

ORD

O'Hare Intl.

$113 Roundtrip, found 1 day ago

$113

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, May 8 from LaGuardia to O'Hare Intl., returning Mon, May 13, priced at $113 found 1 day ago

Sat, May 11 - Wed, May 15

LGA

LaGuardia

ORD

O'Hare Intl.

$119 Roundtrip, found 1 day ago

$119

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, May 11 from LaGuardia to O'Hare Intl., returning Wed, May 15, priced at $119 found 1 day ago

Tue, May 21 - Wed, May 29

LGA

LaGuardia

ORD

O'Hare Intl.

$120 Roundtrip, found 3 days ago

$120

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, May 21 from LaGuardia to O'Hare Intl., returning Wed, May 29, priced at $120 found 3 days ago

Tue, May 21 - Wed, May 29

LGA

LaGuardia

ORD

O'Hare Intl.

$127 Roundtrip, found 3 days ago

$127

Roundtrip

found 3 days ago

Select United flight, departing Tue, May 21 from LaGuardia to O'Hare Intl., returning Wed, May 29, priced at $127 found 3 days ago

Tue, May 21 - Wed, May 29

LGA

LaGuardia

ORD

O'Hare Intl.

$127 Roundtrip, found 3 days ago

$127

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, May 21 from LaGuardia to O'Hare Intl., returning Wed, May 29, priced at $127 found 3 days ago

Tue, May 21 - Wed, May 29

LGA

LaGuardia

ORD

O'Hare Intl.

$127 Roundtrip, found 3 days ago

$127

Roundtrip

found 3 days ago

Select American Airlines flight, departing Tue, May 21 from LaGuardia to O'Hare Intl., returning Wed, May 29, priced at $127 found 3 days ago

Thu, May 2 - Tue, May 7

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$148 Roundtrip, found 6 days ago

$148

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, May 2 from John F. Kennedy Intl. to O'Hare Intl., returning Tue, May 7, priced at $148 found 6 days ago

Wed, May 29 - Tue, Jun 4

EWR

Liberty Intl.

ORD

O'Hare Intl.

$178 Roundtrip, found 1 hour ago

$178

Roundtrip

found 1 hour ago

Select Spirit Airlines flight, departing Wed, May 29 from Liberty Intl. to O'Hare Intl., returning Tue, Jun 4, priced at $178 found 1 hour ago

Wed, May 22 - Sat, May 25

EWR

Liberty Intl.

MDW

Midway Intl.

$188 Roundtrip, found 5 days ago

$188

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, May 22 from Liberty Intl. to Midway Intl., returning Sat, May 25, priced at $188 found 5 days ago