Flights from Chicago to Chappaqua

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

$118 Roundtrip, found 2 days ago

$118

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $118 found 2 days ago

Sun, Sep 14 - Thu, Sep 18

ORD

O'Hare Intl.

LGA

LaGuardia

$120 Roundtrip, found 5 days ago

$120

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to LaGuardia, returning Thu, Sep 18, priced at $120 found 5 days ago

Thu, Sep 11 - Mon, Sep 15

ORD

O'Hare Intl.

LGA

LaGuardia

$130 Roundtrip, found 5 days ago

$130

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Sep 11 from O'Hare Intl. to LaGuardia, returning Mon, Sep 15, priced at $130 found 5 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$134 Roundtrip, found 2 days ago

$134

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $134 found 2 days ago

Tue, Jun 17 - Tue, Jun 17

ORD

O'Hare Intl.

LGA

LaGuardia

$140 Roundtrip, found 10 hours ago

$140

Roundtrip

found 10 hours ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to LaGuardia, returning Tue, Jun 17, priced at $140 found 10 hours ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$141 Roundtrip, found 2 days ago

$141

Roundtrip

found 2 days ago

Select United flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $141 found 2 days ago

Tue, Jul 22 - Sat, Aug 2

ORD

O'Hare Intl.

LGA

LaGuardia

$145 Roundtrip, found 5 days ago

$145

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to LaGuardia, returning Sat, Aug 2, priced at $145 found 5 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$146 Roundtrip, found 2 days ago

$146

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $146 found 2 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$148 Roundtrip, found 2 days ago

$148

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $148 found 2 days ago

Sun, Sep 14 - Thu, Sep 18

ORD

O'Hare Intl.

LGA

LaGuardia

$154 Roundtrip, found 5 days ago

$154

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to LaGuardia, returning Thu, Sep 18, priced at $154 found 5 days ago

Tue, Jun 17 - Fri, Jun 20

ORD

O'Hare Intl.

LGA

LaGuardia

$155 Roundtrip, found 10 hours ago

$155

Roundtrip

found 10 hours ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to LaGuardia, returning Fri, Jun 20, priced at $155 found 10 hours ago

Tue, Sep 16 - Tue, Sep 16

ORD

O'Hare Intl.

LGA

LaGuardia

$157 Roundtrip, found 5 days ago

$157

Roundtrip

found 5 days ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to LaGuardia, returning Tue, Sep 16, priced at $157 found 5 days ago

Wed, Jun 18 - Wed, Jun 18

ORD

O'Hare Intl.

LGA

LaGuardia

$158 Roundtrip, found 5 days ago

$158

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to LaGuardia, returning Wed, Jun 18, priced at $158 found 5 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$164 Roundtrip, found 2 days ago

$164

Roundtrip

found 2 days ago

Select United flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $164 found 2 days ago

Tue, Jun 17 - Sat, Jun 21

ORD

O'Hare Intl.

LGA

LaGuardia

$165 Roundtrip, found 1 day ago

$165

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to LaGuardia, returning Sat, Jun 21, priced at $165 found 1 day ago

Fri, Jun 20 - Mon, Jun 23

ORD

O'Hare Intl.

LGA

LaGuardia

$168 Roundtrip, found 1 day ago

$168

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to LaGuardia, returning Mon, Jun 23, priced at $168 found 1 day ago

Sat, Jun 28 - Mon, Jun 30

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 28 from O'Hare Intl. to LaGuardia, returning Mon, Jun 30, priced at $170 found 2 days ago

Thu, Jun 19 - Fri, Jun 20

ORD

O'Hare Intl.

LGA

LaGuardia

$170 Roundtrip, found 10 hours ago

$170

Roundtrip

found 10 hours ago

Select Spirit Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to LaGuardia, returning Fri, Jun 20, priced at $170 found 10 hours ago

Sun, Sep 14 - Thu, Sep 18

ORD

O'Hare Intl.

LGA

LaGuardia

$192 Roundtrip, found 5 days ago

$192

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to LaGuardia, returning Thu, Sep 18, priced at $192 found 5 days ago

Tue, Jun 17 - Sat, Jun 21

ORD

O'Hare Intl.

LGA

LaGuardia

$217 Roundtrip, found 1 day ago

$217

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to LaGuardia, returning Sat, Jun 21, priced at $217 found 1 day ago