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.

Tue, Jul 29 - Wed, Aug 6

ORD

O'Hare Intl.

LGA

LaGuardia

$136 Roundtrip, found 14 hours ago

$136

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to LaGuardia, returning Wed, Aug 6, priced at $136 found 14 hours ago

Tue, Jul 29 - Tue, Aug 5

ORD

O'Hare Intl.

LGA

LaGuardia

$150 Roundtrip, found 14 hours ago

$150

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to LaGuardia, returning Tue, Aug 5, priced at $150 found 14 hours ago

Wed, Aug 13 - Tue, Aug 19

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$157 Roundtrip, found 3 days ago

$157

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Wed, Aug 13 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Aug 19, priced at $157 found 3 days ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$157 Roundtrip, just found

$157

Roundtrip

just found

Select American Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $157 just found

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$157 Roundtrip, just found

$157

Roundtrip

just found

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $157 just found

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$157 Roundtrip, just found

$157

Roundtrip

just found

Select Delta flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $157 just found

Wed, Aug 13 - Mon, Aug 18

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$162 Roundtrip, found 3 days ago

$162

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Wed, Aug 13 from O'Hare Intl. to John F. Kennedy Intl., returning Mon, Aug 18, priced at $162 found 3 days ago

Mon, Aug 18 - Tue, Aug 19

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$163 Roundtrip, found 3 days ago

$163

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Mon, Aug 18 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Aug 19, priced at $163 found 3 days ago

Sun, Aug 3 - Tue, Aug 5

ORD

O'Hare Intl.

LGA

LaGuardia

$164 Roundtrip, found 14 hours ago

$164

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Sun, Aug 3 from O'Hare Intl. to LaGuardia, returning Tue, Aug 5, priced at $164 found 14 hours ago

Tue, Jul 29 - Sat, Aug 2

ORD

O'Hare Intl.

LGA

LaGuardia

$165 Roundtrip, found 14 hours ago

$165

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to LaGuardia, returning Sat, Aug 2, priced at $165 found 14 hours ago

Tue, Jul 29 - Thu, Aug 7

ORD

O'Hare Intl.

LGA

LaGuardia

$167 Roundtrip, found 14 hours ago

$167

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to LaGuardia, returning Thu, Aug 7, priced at $167 found 14 hours ago

Mon, Aug 18 - Mon, Aug 18

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$169 Roundtrip, found 3 days ago

$169

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Mon, Aug 18 from O'Hare Intl. to John F. Kennedy Intl., returning Mon, Aug 18, priced at $169 found 3 days ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$172 Roundtrip, just found

$172

Roundtrip

just found

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $172 just found

Fri, Aug 15 - Tue, Aug 19

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$177 Roundtrip, found 3 days ago

$177

Roundtrip

found 3 days ago

Select Delta flight, departing Fri, Aug 15 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Aug 19, priced at $177 found 3 days ago

Sat, Aug 2 - Tue, Aug 5

ORD

O'Hare Intl.

LGA

LaGuardia

$179 Roundtrip, found 14 hours ago

$179

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to LaGuardia, returning Tue, Aug 5, priced at $179 found 14 hours ago

Sun, Aug 3 - Thu, Aug 7

ORD

O'Hare Intl.

LGA

LaGuardia

$181 Roundtrip, found 14 hours ago

$181

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Sun, Aug 3 from O'Hare Intl. to LaGuardia, returning Thu, Aug 7, priced at $181 found 14 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$182 Roundtrip, just found

$182

Roundtrip

just found

Select Delta flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $182 just found

Thu, Nov 6 - Sun, Nov 9

ORD

O'Hare Intl.

LGA

LaGuardia

$183 Roundtrip, found 6 days ago

$183

Roundtrip

found 6 days ago

Select United flight, departing Thu, Nov 6 from O'Hare Intl. to LaGuardia, returning Sun, Nov 9, priced at $183 found 6 days ago

Tue, Jul 8 - Wed, Jul 9

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$264 Roundtrip, found 5 days ago

$264

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to John F. Kennedy Intl., returning Wed, Jul 9, priced at $264 found 5 days ago

Tue, Jul 8 - Sat, Jul 12

ORD

O'Hare Intl.

HPN

Westchester County

$439 Roundtrip, found 2 days ago

$439

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Jul 8 from O'Hare Intl. to Westchester County, returning Sat, Jul 12, priced at $439 found 2 days ago