Flights from Chicago to Old Greenwich

Cheapest flights from Chicago

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.

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$109 Roundtrip, found 5 days ago

$109

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $109 found 5 days ago

Tue, Jul 29 - Sat, Aug 2

ORD

O'Hare Intl.

LGA

LaGuardia

$110 Roundtrip, just found

$110

Roundtrip

just found

Select Spirit Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to LaGuardia, returning Sat, Aug 2, priced at $110 just found

Thu, Jun 5 - Thu, Jun 12

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$117 Roundtrip, found 5 days ago

$117

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Thu, Jun 5 from O'Hare Intl. to John F. Kennedy Intl., returning Thu, Jun 12, priced at $117 found 5 days ago

Wed, Jun 4 - Tue, Jun 17

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$117 Roundtrip, found 5 days ago

$117

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Jun 4 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Jun 17, priced at $117 found 5 days ago

Tue, Jul 29 - Sat, Aug 2

ORD

O'Hare Intl.

LGA

LaGuardia

$120 Roundtrip, just found

$120

Roundtrip

just found

Select Spirit Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to LaGuardia, returning Sat, Aug 2, priced at $120 just found

Sat, Jun 21 - Wed, Jun 25

ORD

O'Hare Intl.

LGA

LaGuardia

$125 Roundtrip, found 5 days ago

$125

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Wed, Jun 25, priced at $125 found 5 days ago

Fri, Nov 14 - Tue, Nov 18

ORD

O'Hare Intl.

LGA

LaGuardia

$134 Roundtrip, found 5 hours ago

$134

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Fri, Nov 14 from O'Hare Intl. to LaGuardia, returning Tue, Nov 18, priced at $134 found 5 hours ago

Sat, Jul 26 - Sat, Aug 2

ORD

O'Hare Intl.

LGA

LaGuardia

$135 Roundtrip, just found

$135

Roundtrip

just found

Select Spirit Airlines flight, departing Sat, Jul 26 from O'Hare Intl. to LaGuardia, returning Sat, Aug 2, priced at $135 just found

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$137 Roundtrip, found 5 days ago

$137

Roundtrip

found 5 days ago

Select United flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $137 found 5 days ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$142 Roundtrip, found 5 days ago

$142

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $142 found 5 days ago

Fri, Nov 14 - Tue, Nov 18

ORD

O'Hare Intl.

LGA

LaGuardia

$143 Roundtrip, found 5 hours ago

$143

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Fri, Nov 14 from O'Hare Intl. to LaGuardia, returning Tue, Nov 18, priced at $143 found 5 hours ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$145 Roundtrip, found 5 days ago

$145

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $145 found 5 days ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$147 Roundtrip, found 5 days ago

$147

Roundtrip

found 5 days ago

Select United flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $147 found 5 days ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$147 Roundtrip, found 5 days ago

$147

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $147 found 5 days ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$148 Roundtrip, found 5 days ago

$148

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $148 found 5 days ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$150 Roundtrip, found 5 days ago

$150

Roundtrip

found 5 days ago

Select United flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $150 found 5 days ago

Wed, Sep 3 - Wed, Sep 3

ORD

O'Hare Intl.

LGA

LaGuardia

$152 Roundtrip, found 9 hours ago

$152

Roundtrip

found 9 hours ago

Select Delta flight, departing Wed, Sep 3 from O'Hare Intl. to LaGuardia, returning Wed, Sep 3, priced at $152 found 9 hours ago

Fri, Jun 20 - Mon, Jun 23

MDW

Midway Intl.

JFK

John F. Kennedy Intl.

$174 Roundtrip, found 4 days ago

$174

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Jun 20 from Midway Intl. to John F. Kennedy Intl., returning Mon, Jun 23, priced at $174 found 4 days ago

Mon, Jun 16 - Thu, Jun 26

MDW

Midway Intl.

LGA

LaGuardia

$195 Roundtrip, found 4 days ago

$195

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Mon, Jun 16 from Midway Intl. to LaGuardia, returning Thu, Jun 26, priced at $195 found 4 days ago

Tue, Jun 10 - Tue, Jun 17

ORD

O'Hare Intl.

HPN

Westchester County

$297 Roundtrip, found 1 hour ago

$297

Roundtrip

found 1 hour ago

Select Delta flight, departing Tue, Jun 10 from O'Hare Intl. to Westchester County, returning Tue, Jun 17, priced at $297 found 1 hour ago