Flights from Chicago to Rye Brook

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 4 days ago

$118

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $118 found 4 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$134 Roundtrip, found 4 days ago

$134

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $134 found 4 days ago

Wed, Sep 10 - Wed, Sep 17

ORD

O'Hare Intl.

LGA

LaGuardia

$140 Roundtrip, found 6 hours ago

$140

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Wed, Sep 10 from O'Hare Intl. to LaGuardia, returning Wed, Sep 17, priced at $140 found 6 hours ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$141 Roundtrip, found 4 days ago

$141

Roundtrip

found 4 days ago

Select United flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $141 found 4 days ago

Tue, Jul 1 - Fri, Jul 4

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$142 Roundtrip, found 1 day ago

$142

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Tue, Jul 1 from O'Hare Intl. to John F. Kennedy Intl., returning Fri, Jul 4, priced at $142 found 1 day ago

Tue, Oct 14 - Wed, Oct 15

ORD

O'Hare Intl.

LGA

LaGuardia

$143 Roundtrip, found 12 hours ago

$143

Roundtrip

found 12 hours ago

Select Delta flight, departing Tue, Oct 14 from O'Hare Intl. to LaGuardia, returning Wed, Oct 15, priced at $143 found 12 hours ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$146 Roundtrip, found 4 days ago

$146

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $146 found 4 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$148 Roundtrip, found 4 days ago

$148

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $148 found 4 days ago

Wed, Sep 10 - Fri, Sep 19

ORD

O'Hare Intl.

LGA

LaGuardia

$155 Roundtrip, found 6 hours ago

$155

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Wed, Sep 10 from O'Hare Intl. to LaGuardia, returning Fri, Sep 19, priced at $155 found 6 hours ago

Tue, Sep 23 - Tue, Sep 30

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$157 Roundtrip, found 5 days ago

$157

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Tue, Sep 23 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Sep 30, priced at $157 found 5 days ago

Fri, Sep 12 - Sun, Sep 21

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$160 Roundtrip, found 6 hours ago

$160

Roundtrip

found 6 hours ago

Select JetBlue Airways flight, departing Fri, Sep 12 from O'Hare Intl. to John F. Kennedy Intl., returning Sun, Sep 21, priced at $160 found 6 hours ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$164 Roundtrip, found 4 days ago

$164

Roundtrip

found 4 days ago

Select United flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $164 found 4 days ago

Tue, Jun 17 - Sat, Jun 21

ORD

O'Hare Intl.

LGA

LaGuardia

$165 Roundtrip, found 3 days ago

$165

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to LaGuardia, returning Sat, Jun 21, priced at $165 found 3 days ago

Tue, Sep 23 - Mon, Sep 29

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$167 Roundtrip, found 5 days ago

$167

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Tue, Sep 23 from O'Hare Intl. to John F. Kennedy Intl., returning Mon, Sep 29, priced at $167 found 5 days ago

Fri, Jun 20 - Mon, Jun 23

ORD

O'Hare Intl.

LGA

LaGuardia

$168 Roundtrip, found 3 days ago

$168

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to LaGuardia, returning Mon, Jun 23, priced at $168 found 3 days ago

Sat, Jun 28 - Mon, Jun 30

ORD

O'Hare Intl.

LGA

LaGuardia

$170 Roundtrip, found 4 days ago

$170

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Mon, Jun 30, priced at $170 found 4 days ago

Thu, Jun 19 - Fri, Jun 20

ORD

O'Hare Intl.

LGA

LaGuardia

$170 Roundtrip, found 2 days ago

$170

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to LaGuardia, returning Fri, Jun 20, priced at $170 found 2 days ago

Thu, Sep 18 - Tue, Sep 23

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$172 Roundtrip, found 5 days ago

$172

Roundtrip

found 5 days ago

Select American Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Sep 23, priced at $172 found 5 days ago

Tue, Oct 7 - Sat, Oct 11

MDW

Midway Intl.

LGA

LaGuardia

$204 Roundtrip, found 12 hours ago

$204

Roundtrip

found 12 hours ago

Select Frontier Airlines flight, departing Tue, Oct 7 from Midway Intl. to LaGuardia, returning Sat, Oct 11, priced at $204 found 12 hours ago

Wed, Aug 20 - Fri, Aug 22

MDW

Midway Intl.

JFK

John F. Kennedy Intl.

$297 Roundtrip, found 6 days ago

$297

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Aug 20 from Midway Intl. to John F. Kennedy Intl., returning Fri, Aug 22, priced at $297 found 6 days ago