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.

Thu, Oct 30 - Mon, Nov 3

LGA

LaGuardia

ORD

O'Hare Intl.

$102 Roundtrip, found 2 days ago

$102

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Oct 30 from LaGuardia to O'Hare Intl., returning Mon, Nov 3, priced at $102 found 2 days ago

Mon, Oct 27 - Fri, Oct 31

LGA

LaGuardia

ORD

O'Hare Intl.

$112 Roundtrip, found 2 days ago

$112

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Oct 27 from LaGuardia to O'Hare Intl., returning Fri, Oct 31, priced at $112 found 2 days ago

Thu, Oct 30 - Mon, Nov 3

LGA

LaGuardia

ORD

O'Hare Intl.

$128 Roundtrip, found 2 days ago

$128

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Oct 30 from LaGuardia to O'Hare Intl., returning Mon, Nov 3, priced at $128 found 2 days ago

Thu, Oct 30 - Mon, Nov 3

LGA

LaGuardia

ORD

O'Hare Intl.

$135 Roundtrip, found 2 days ago

$135

Roundtrip

found 2 days ago

Select United flight, departing Thu, Oct 30 from LaGuardia to O'Hare Intl., returning Mon, Nov 3, priced at $135 found 2 days ago

Sun, Aug 17 - Tue, Aug 19

LGA

LaGuardia

ORD

O'Hare Intl.

$136 Roundtrip, found 5 days ago

$136

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sun, Aug 17 from LaGuardia to O'Hare Intl., returning Tue, Aug 19, priced at $136 found 5 days ago

Tue, Aug 19 - Tue, Aug 26

LGA

LaGuardia

ORD

O'Hare Intl.

$137 Roundtrip, found 5 days ago

$137

Roundtrip

found 5 days ago

Select Delta flight, departing Tue, Aug 19 from LaGuardia to O'Hare Intl., returning Tue, Aug 26, priced at $137 found 5 days ago

Thu, Oct 30 - Mon, Nov 3

LGA

LaGuardia

ORD

O'Hare Intl.

$145 Roundtrip, found 2 days ago

$145

Roundtrip

found 2 days ago

Select United flight, departing Thu, Oct 30 from LaGuardia to O'Hare Intl., returning Mon, Nov 3, priced at $145 found 2 days ago

Sat, Sep 13 - Tue, Sep 16

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$147 Roundtrip, found 3 hours ago

$147

Roundtrip

found 3 hours ago

Select Delta flight, departing Sat, Sep 13 from John F. Kennedy Intl. to O'Hare Intl., returning Tue, Sep 16, priced at $147 found 3 hours ago

Sun, Aug 17 - Tue, Aug 19

LGA

LaGuardia

ORD

O'Hare Intl.

$151 Roundtrip, found 5 days ago

$151

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sun, Aug 17 from LaGuardia to O'Hare Intl., returning Tue, Aug 19, priced at $151 found 5 days ago

Thu, Oct 30 - Mon, Nov 3

LGA

LaGuardia

ORD

O'Hare Intl.

$152 Roundtrip, found 2 days ago

$152

Roundtrip

found 2 days ago

Select United flight, departing Thu, Oct 30 from LaGuardia to O'Hare Intl., returning Mon, Nov 3, priced at $152 found 2 days ago

Tue, Aug 26 - Wed, Aug 27

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$157 Roundtrip, found 5 days ago

$157

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Tue, Aug 26 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Aug 27, priced at $157 found 5 days ago

Thu, Oct 30 - Mon, Nov 3

LGA

LaGuardia

ORD

O'Hare Intl.

$161 Roundtrip, found 2 days ago

$161

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Oct 30 from LaGuardia to O'Hare Intl., returning Mon, Nov 3, priced at $161 found 2 days ago

Wed, Aug 20 - Tue, Aug 26

LGA

LaGuardia

ORD

O'Hare Intl.

$162 Roundtrip, found 3 hours ago

$162

Roundtrip

found 3 hours ago

Select Delta flight, departing Wed, Aug 20 from LaGuardia to O'Hare Intl., returning Tue, Aug 26, priced at $162 found 3 hours ago

Wed, Sep 10 - Sat, Sep 13

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$172 Roundtrip, found 3 hours ago

$172

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Wed, Sep 10 from John F. Kennedy Intl. to O'Hare Intl., returning Sat, Sep 13, priced at $172 found 3 hours ago

Wed, Sep 10 - Sat, Sep 13

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$174 Roundtrip, found 3 hours ago

$174

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Wed, Sep 10 from John F. Kennedy Intl. to O'Hare Intl., returning Sat, Sep 13, priced at $174 found 3 hours ago

Thu, Oct 30 - Mon, Nov 3

LGA

LaGuardia

ORD

O'Hare Intl.

$177 Roundtrip, found 2 days ago

$177

Roundtrip

found 2 days ago

Select United flight, departing Thu, Oct 30 from LaGuardia to O'Hare Intl., returning Mon, Nov 3, priced at $177 found 2 days ago

Wed, Aug 13 - Sat, Aug 16

EWR

Newark Liberty Intl. Airport

ORD

O'Hare Intl.

$179 Roundtrip, found 1 day ago

$179

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Aug 13 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Aug 16, priced at $179 found 1 day ago

Thu, Aug 14 - Sat, Aug 16

LGA

LaGuardia

MDW

Midway Intl.

$218 Roundtrip, found 4 hours ago

$218

Roundtrip

found 4 hours ago

Select Frontier Airlines flight, departing Thu, Aug 14 from LaGuardia to Midway Intl., returning Sat, Aug 16, priced at $218 found 4 hours ago

Wed, Aug 13 - Wed, Aug 20

EWR

Newark Liberty Intl. Airport

MDW

Midway Intl.

$223 Roundtrip, found 4 hours ago

$223

Roundtrip

found 4 hours ago

Select Delta flight, departing Wed, Aug 13 from Newark Liberty Intl. Airport to Midway Intl., returning Wed, Aug 20, priced at $223 found 4 hours ago

Sat, Aug 16 - Fri, Aug 22

JFK

John F. Kennedy Intl.

MDW

Midway Intl.

$238 Roundtrip, found 9 hours ago

$238

Roundtrip

found 9 hours ago

Select Frontier Airlines flight, departing Sat, Aug 16 from John F. Kennedy Intl. to Midway Intl., returning Fri, Aug 22, priced at $238 found 9 hours ago