Flights from Chicago to Ossining

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.

Sun, Sep 14 - Thu, Sep 18

ORD

O'Hare Intl.

LGA

LaGuardia

$120 Roundtrip, found 8 hours ago

$120

Roundtrip

found 8 hours ago

Select Spirit Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to LaGuardia, returning Thu, Sep 18, priced at $120 found 8 hours ago

Thu, Sep 11 - Mon, Sep 15

ORD

O'Hare Intl.

LGA

LaGuardia

$130 Roundtrip, found 8 hours ago

$130

Roundtrip

found 8 hours ago

Select Spirit Airlines flight, departing Thu, Sep 11 from O'Hare Intl. to LaGuardia, returning Mon, Sep 15, priced at $130 found 8 hours ago

Tue, Jul 22 - Sat, Aug 2

ORD

O'Hare Intl.

LGA

LaGuardia

$145 Roundtrip, found 1 hour ago

$145

Roundtrip

found 1 hour ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to LaGuardia, returning Sat, Aug 2, priced at $145 found 1 hour ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

LGA

LaGuardia

$149 Roundtrip, found 2 days ago

$149

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to LaGuardia, returning Sat, Jun 21, priced at $149 found 2 days ago

Fri, Aug 8 - Wed, Aug 13

ORD

O'Hare Intl.

LGA

LaGuardia

$150 Roundtrip, found 5 days ago

$150

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to LaGuardia, returning Wed, Aug 13, priced at $150 found 5 days ago

Sun, Sep 14 - Thu, Sep 18

ORD

O'Hare Intl.

LGA

LaGuardia

$154 Roundtrip, found 8 hours ago

$154

Roundtrip

found 8 hours ago

Select Spirit Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to LaGuardia, returning Thu, Sep 18, priced at $154 found 8 hours ago

Sat, Jun 21 - Thu, Jun 26

ORD

O'Hare Intl.

LGA

LaGuardia

$155 Roundtrip, found 4 days ago

$155

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Thu, Jun 26, priced at $155 found 4 days ago

Tue, Sep 16 - Tue, Sep 16

ORD

O'Hare Intl.

LGA

LaGuardia

$157 Roundtrip, found 8 hours ago

$157

Roundtrip

found 8 hours ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to LaGuardia, returning Tue, Sep 16, priced at $157 found 8 hours ago

Sun, Sep 14 - Thu, Sep 18

ORD

O'Hare Intl.

LGA

LaGuardia

$158 Roundtrip, found 8 hours ago

$158

Roundtrip

found 8 hours ago

Select Spirit Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to LaGuardia, returning Thu, Sep 18, priced at $158 found 8 hours ago

Sun, Sep 14 - Thu, Sep 18

ORD

O'Hare Intl.

LGA

LaGuardia

$165 Roundtrip, found 8 hours ago

$165

Roundtrip

found 8 hours ago

Select American Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to LaGuardia, returning Thu, Sep 18, priced at $165 found 8 hours ago

Thu, Sep 11 - Sun, Sep 21

ORD

O'Hare Intl.

LGA

LaGuardia

$165 Roundtrip, found 8 hours ago

$165

Roundtrip

found 8 hours ago

Select Spirit Airlines flight, departing Thu, Sep 11 from O'Hare Intl. to LaGuardia, returning Sun, Sep 21, priced at $165 found 8 hours ago

Mon, Aug 11 - Wed, Aug 13

ORD

O'Hare Intl.

LGA

LaGuardia

$167 Roundtrip, found 5 days ago

$167

Roundtrip

found 5 days ago

Select United flight, departing Mon, Aug 11 from O'Hare Intl. to LaGuardia, returning Wed, Aug 13, priced at $167 found 5 days ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

LGA

LaGuardia

$170 Roundtrip, found 2 days ago

$170

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to LaGuardia, returning Sat, Jun 21, priced at $170 found 2 days ago

Wed, Jun 11 - Wed, Jun 18

ORD

O'Hare Intl.

LGA

LaGuardia

$173 Roundtrip, found 2 days ago

$173

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 11 from O'Hare Intl. to LaGuardia, returning Wed, Jun 18, priced at $173 found 2 days ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

LGA

LaGuardia

$175 Roundtrip, found 2 days ago

$175

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to LaGuardia, returning Sat, Jun 21, priced at $175 found 2 days ago

Fri, Aug 8 - Tue, Aug 12

ORD

O'Hare Intl.

LGA

LaGuardia

$178 Roundtrip, found 5 days ago

$178

Roundtrip

found 5 days ago

Select Delta flight, departing Fri, Aug 8 from O'Hare Intl. to LaGuardia, returning Tue, Aug 12, priced at $178 found 5 days ago

Fri, Aug 8 - Mon, Aug 18

ORD

O'Hare Intl.

LGA

LaGuardia

$179 Roundtrip, found 5 days ago

$179

Roundtrip

found 5 days ago

Select Delta flight, departing Fri, Aug 8 from O'Hare Intl. to LaGuardia, returning Mon, Aug 18, priced at $179 found 5 days ago

Mon, Aug 11 - Wed, Aug 13

ORD

O'Hare Intl.

LGA

LaGuardia

$180 Roundtrip, found 5 days ago

$180

Roundtrip

found 5 days ago

Select United flight, departing Mon, Aug 11 from O'Hare Intl. to LaGuardia, returning Wed, Aug 13, priced at $180 found 5 days ago

Sun, Sep 14 - Thu, Sep 18

ORD

O'Hare Intl.

LGA

LaGuardia

$192 Roundtrip, found 8 hours ago

$192

Roundtrip

found 8 hours ago

Select American Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to LaGuardia, returning Thu, Sep 18, priced at $192 found 8 hours ago

Mon, Jun 16 - Wed, Jun 18

ORD

O'Hare Intl.

LGA

LaGuardia

$219 Roundtrip, found 2 days ago

$219

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Mon, Jun 16 from O'Hare Intl. to LaGuardia, returning Wed, Jun 18, priced at $219 found 2 days ago