Flights from Stamford to Chicago

Cheapest flights from Stamford

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.

Tue, Aug 26 - Wed, Sep 3

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$138 Roundtrip, found 2 hours ago

$138

Roundtrip

found 2 hours ago

Select JetBlue Airways flight, departing Tue, Aug 26 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Sep 3, priced at $138 found 2 hours ago

Sat, Sep 27 - Sat, Oct 4

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$139 Roundtrip, found 10 hours ago

$139

Roundtrip

found 10 hours ago

Select JetBlue Airways flight, departing Sat, Sep 27 from John F. Kennedy Intl. to O'Hare Intl., returning Sat, Oct 4, priced at $139 found 10 hours ago

Wed, Sep 24 - Wed, Oct 1

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$143 Roundtrip, found 10 hours ago

$143

Roundtrip

found 10 hours ago

Select American Airlines flight, departing Wed, Sep 24 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Oct 1, priced at $143 found 10 hours ago

Tue, Sep 23 - Tue, Sep 30

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$147 Roundtrip, found 10 hours ago

$147

Roundtrip

found 10 hours ago

Select Delta flight, departing Tue, Sep 23 from John F. Kennedy Intl. to O'Hare Intl., returning Tue, Sep 30, priced at $147 found 10 hours ago

Thu, Aug 21 - Tue, Aug 26

LGA

LaGuardia

ORD

O'Hare Intl.

$149 Roundtrip, found 4 days ago

$149

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Aug 21 from LaGuardia to O'Hare Intl., returning Tue, Aug 26, priced at $149 found 4 days ago

Sat, Sep 27 - Sun, Sep 28

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$154 Roundtrip, found 10 hours ago

$154

Roundtrip

found 10 hours ago

Select JetBlue Airways flight, departing Sat, Sep 27 from John F. Kennedy Intl. to O'Hare Intl., returning Sun, Sep 28, priced at $154 found 10 hours ago

Sat, Aug 23 - Tue, Aug 26

LGA

LaGuardia

ORD

O'Hare Intl.

$157 Roundtrip, found 4 days ago

$157

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Aug 23 from LaGuardia to O'Hare Intl., returning Tue, Aug 26, priced at $157 found 4 days ago

Thu, Aug 21 - Tue, Aug 26

LGA

LaGuardia

ORD

O'Hare Intl.

$160 Roundtrip, found 4 days ago

$160

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Aug 21 from LaGuardia to O'Hare Intl., returning Tue, Aug 26, priced at $160 found 4 days ago

Thu, Aug 21 - Tue, Aug 26

LGA

LaGuardia

ORD

O'Hare Intl.

$162 Roundtrip, found 4 days ago

$162

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Aug 21 from LaGuardia to O'Hare Intl., returning Tue, Aug 26, priced at $162 found 4 days ago

Wed, Aug 20 - Tue, Aug 26

LGA

LaGuardia

ORD

O'Hare Intl.

$162 Roundtrip, found 6 days ago

$162

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Aug 20 from LaGuardia to O'Hare Intl., returning Tue, Aug 26, priced at $162 found 6 days ago

Mon, Sep 8 - Tue, Sep 16

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$163 Roundtrip, found 6 days ago

$163

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Mon, Sep 8 from John F. Kennedy Intl. to O'Hare Intl., returning Tue, Sep 16, priced at $163 found 6 days ago

Sat, Aug 23 - Wed, Aug 27

LGA

LaGuardia

ORD

O'Hare Intl.

$166 Roundtrip, found 4 days ago

$166

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Aug 23 from LaGuardia to O'Hare Intl., returning Wed, Aug 27, priced at $166 found 4 days ago

Tue, Sep 23 - Thu, Oct 2

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$167 Roundtrip, found 10 hours ago

$167

Roundtrip

found 10 hours ago

Select Delta flight, departing Tue, Sep 23 from John F. Kennedy Intl. to O'Hare Intl., returning Thu, Oct 2, priced at $167 found 10 hours ago

Wed, Sep 24 - Wed, Oct 1

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$168 Roundtrip, found 10 hours ago

$168

Roundtrip

found 10 hours ago

Select American Airlines flight, departing Wed, Sep 24 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Oct 1, priced at $168 found 10 hours ago

Wed, Sep 24 - Wed, Oct 1

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$169 Roundtrip, found 10 hours ago

$169

Roundtrip

found 10 hours ago

Select Frontier Airlines flight, departing Wed, Sep 24 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Oct 1, priced at $169 found 10 hours ago

Thu, Aug 21 - Tue, Aug 26

LGA

LaGuardia

ORD

O'Hare Intl.

$170 Roundtrip, found 4 days ago

$170

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Aug 21 from LaGuardia to O'Hare Intl., returning Tue, Aug 26, priced at $170 found 4 days ago

Sat, Aug 30 - Wed, Sep 3

LGA

LaGuardia

MDW

Midway Intl.

$208 Roundtrip, found 3 days ago

$208

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Aug 30 from LaGuardia to Midway Intl., returning Wed, Sep 3, priced at $208 found 3 days ago

Tue, Sep 23 - Tue, Sep 30

JFK

John F. Kennedy Intl.

MDW

Midway Intl.

$217 Roundtrip, found 1 day ago

$217

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Sep 23 from John F. Kennedy Intl. to Midway Intl., returning Tue, Sep 30, priced at $217 found 1 day ago

Thu, Aug 28 - Sat, Aug 30

LGA

LaGuardia

ORD

O'Hare Intl.

$225 Roundtrip, found 2 hours ago

$225

Roundtrip

found 2 hours ago

Select United flight, departing Thu, Aug 28 from LaGuardia to O'Hare Intl., returning Sat, Aug 30, priced at $225 found 2 hours ago

Sat, Sep 13 - Sun, Sep 14

ISP

MacArthur

ORD

O'Hare Intl.

$238 Roundtrip, found 6 days ago

$238

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Sep 13 from MacArthur to O'Hare Intl., returning Sun, Sep 14, priced at $238 found 6 days ago