Flights from Chicago to Pound Ridge

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 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$130 Roundtrip, found 3 days ago

$130

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $130 found 3 days ago

Wed, Jul 16 - Wed, Jul 16

ORD

O'Hare Intl.

LGA

LaGuardia

$140 Roundtrip, found 1 day ago

$140

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to LaGuardia, returning Wed, Jul 16, priced at $140 found 1 day ago

Tue, Oct 14 - Wed, Oct 15

ORD

O'Hare Intl.

LGA

LaGuardia

$143 Roundtrip, found 3 days ago

$143

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Oct 14 from O'Hare Intl. to LaGuardia, returning Wed, Oct 15, priced at $143 found 3 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$146 Roundtrip, found 3 days ago

$146

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $146 found 3 days ago

Wed, Jul 16 - Sat, Jul 19

ORD

O'Hare Intl.

LGA

LaGuardia

$155 Roundtrip, found 1 day ago

$155

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to LaGuardia, returning Sat, Jul 19, priced at $155 found 1 day ago

Tue, Oct 14 - Sat, Oct 18

ORD

O'Hare Intl.

LGA

LaGuardia

$160 Roundtrip, found 3 days ago

$160

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Oct 14 from O'Hare Intl. to LaGuardia, returning Sat, Oct 18, priced at $160 found 3 days ago

Sun, Jul 20 - Mon, Jul 21

ORD

O'Hare Intl.

LGA

LaGuardia

$165 Roundtrip, found 1 day ago

$165

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Jul 20 from O'Hare Intl. to LaGuardia, returning Mon, Jul 21, priced at $165 found 1 day ago

Sun, Jul 20 - Mon, Jul 21

ORD

O'Hare Intl.

LGA

LaGuardia

$168 Roundtrip, found 1 day ago

$168

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Jul 20 from O'Hare Intl. to LaGuardia, returning Mon, Jul 21, priced at $168 found 1 day ago

Thu, Jun 19 - Fri, Jun 20

ORD

O'Hare Intl.

LGA

LaGuardia

$170 Roundtrip, found 6 days ago

$170

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to LaGuardia, returning Fri, Jun 20, priced at $170 found 6 days ago

Sun, Jul 20 - Mon, Jul 21

ORD

O'Hare Intl.

LGA

LaGuardia

$175 Roundtrip, found 1 day ago

$175

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Jul 20 from O'Hare Intl. to LaGuardia, returning Mon, Jul 21, priced at $175 found 1 day ago

Thu, Oct 9 - Wed, Oct 15

ORD

O'Hare Intl.

LGA

LaGuardia

$176 Roundtrip, found 3 days ago

$176

Roundtrip

found 3 days ago

Select Delta flight, departing Thu, Oct 9 from O'Hare Intl. to LaGuardia, returning Wed, Oct 15, priced at $176 found 3 days ago

Wed, Jun 18 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$177 Roundtrip, found 6 days ago

$177

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Jun 18 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $177 found 6 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$177 Roundtrip, found 3 days ago

$177

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $177 found 3 days ago

Sun, Jul 20 - Mon, Jul 21

ORD

O'Hare Intl.

LGA

LaGuardia

$183 Roundtrip, found 1 day ago

$183

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Jul 20 from O'Hare Intl. to LaGuardia, returning Mon, Jul 21, priced at $183 found 1 day ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$184 Roundtrip, found 3 days ago

$184

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $184 found 3 days ago

Sat, Jul 19 - Sun, Jul 20

ORD

O'Hare Intl.

LGA

LaGuardia

$185 Roundtrip, found 1 day ago

$185

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to LaGuardia, returning Sun, Jul 20, priced at $185 found 1 day ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$187 Roundtrip, found 3 days ago

$187

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $187 found 3 days ago

Tue, Oct 7 - Sat, Oct 11

MDW

Midway Intl.

LGA

LaGuardia

$204 Roundtrip, found 3 days ago

$204

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Oct 7 from Midway Intl. to LaGuardia, returning Sat, Oct 11, priced at $204 found 3 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$213 Roundtrip, found 3 days ago

$213

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $213 found 3 days ago

Sat, Jun 21 - Tue, Jun 24

MDW

Midway Intl.

HPN

Westchester County

$439 Roundtrip, found 5 hours ago

$439

Roundtrip

found 5 hours ago

Select Delta flight, departing Sat, Jun 21 from Midway Intl. to Westchester County, returning Tue, Jun 24, priced at $439 found 5 hours ago