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

$130 Roundtrip, found 1 day ago

$130

Roundtrip

found 1 day ago

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

Wed, Jul 2 - Wed, Jul 9

ORD

O'Hare Intl.

LGA

LaGuardia

$140 Roundtrip, found 12 hours ago

$140

Roundtrip

found 12 hours ago

Select Spirit Airlines flight, departing Wed, Jul 2 from O'Hare Intl. to LaGuardia, returning Wed, Jul 9, priced at $140 found 12 hours ago

Wed, Jul 2 - Thu, Jul 10

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$141 Roundtrip, found 12 hours ago

$141

Roundtrip

found 12 hours ago

Select JetBlue Airways flight, departing Wed, Jul 2 from O'Hare Intl. to John F. Kennedy Intl., returning Thu, Jul 10, priced at $141 found 12 hours ago

Tue, Jul 1 - Fri, Jul 4

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$142 Roundtrip, found 3 days ago

$142

Roundtrip

found 3 days 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 3 days ago

Tue, Oct 14 - Wed, Oct 15

ORD

O'Hare Intl.

LGA

LaGuardia

$143 Roundtrip, found 2 days ago

$143

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Oct 14 from O'Hare Intl. to LaGuardia, returning Wed, Oct 15, priced at $143 found 2 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$146 Roundtrip, found 1 day ago

$146

Roundtrip

found 1 day ago

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

Sat, Jul 5 - Wed, Jul 9

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$152 Roundtrip, found 12 hours ago

$152

Roundtrip

found 12 hours ago

Select JetBlue Airways flight, departing Sat, Jul 5 from O'Hare Intl. to John F. Kennedy Intl., returning Wed, Jul 9, priced at $152 found 12 hours ago

Thu, Jul 3 - Wed, Jul 9

ORD

O'Hare Intl.

LGA

LaGuardia

$155 Roundtrip, found 12 hours ago

$155

Roundtrip

found 12 hours ago

Select Spirit Airlines flight, departing Thu, Jul 3 from O'Hare Intl. to LaGuardia, returning Wed, Jul 9, priced at $155 found 12 hours ago

Fri, Sep 12 - Sun, Sep 21

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$160 Roundtrip, found 2 days ago

$160

Roundtrip

found 2 days 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 2 days ago

Tue, Jun 17 - Sat, Jun 21

ORD

O'Hare Intl.

LGA

LaGuardia

$165 Roundtrip, found 5 days ago

$165

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to LaGuardia, returning Sat, Jun 21, priced at $165 found 5 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$168 Roundtrip, found 1 day ago

$168

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Tue, Jul 1, priced at $168 found 1 day ago

Sat, Jun 28 - Mon, Jun 30

ORD

O'Hare Intl.

LGA

LaGuardia

$170 Roundtrip, found 6 days ago

$170

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to LaGuardia, returning Mon, Jun 30, priced at $170 found 6 days ago

Thu, Jun 19 - Fri, Jun 20

ORD

O'Hare Intl.

LGA

LaGuardia

$170 Roundtrip, found 4 days ago

$170

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to LaGuardia, returning Fri, Jun 20, priced at $170 found 4 days ago

Wed, Jul 2 - Sat, Jul 12

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$175 Roundtrip, found 12 hours ago

$175

Roundtrip

found 12 hours ago

Select JetBlue Airways flight, departing Wed, Jul 2 from O'Hare Intl. to John F. Kennedy Intl., returning Sat, Jul 12, priced at $175 found 12 hours ago

Thu, Oct 9 - Wed, Oct 15

ORD

O'Hare Intl.

LGA

LaGuardia

$176 Roundtrip, found 2 days ago

$176

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Oct 9 from O'Hare Intl. to LaGuardia, returning Wed, Oct 15, priced at $176 found 2 days ago

Thu, Jul 3 - Thu, Jul 10

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$177 Roundtrip, found 12 hours ago

$177

Roundtrip

found 12 hours ago

Select JetBlue Airways flight, departing Thu, Jul 3 from O'Hare Intl. to John F. Kennedy Intl., returning Thu, Jul 10, priced at $177 found 12 hours ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$177 Roundtrip, found 1 day ago

$177

Roundtrip

found 1 day ago

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

Fri, Jul 4 - Thu, Jul 10

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$178 Roundtrip, found 12 hours ago

$178

Roundtrip

found 12 hours ago

Select JetBlue Airways flight, departing Fri, Jul 4 from O'Hare Intl. to John F. Kennedy Intl., returning Thu, Jul 10, priced at $178 found 12 hours ago

Tue, Oct 7 - Sat, Oct 11

MDW

Midway Intl.

LGA

LaGuardia

$204 Roundtrip, found 2 days ago

$204

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Tue, Oct 7 from Midway Intl. to LaGuardia, returning Sat, Oct 11, priced at $204 found 2 days ago

Sat, Jun 28 - Tue, Jul 1

ORD

O'Hare Intl.

LGA

LaGuardia

$213 Roundtrip, found 1 day ago

$213

Roundtrip

found 1 day ago

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