Flights from Chicago to Shelter Island

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.

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$91 Roundtrip, found 5 hours ago

$91

Roundtrip

found 5 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $91 found 5 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$91 Roundtrip, found 5 hours ago

$91

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $91 found 5 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$110 Roundtrip, found 5 hours ago

$110

Roundtrip

found 5 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $110 found 5 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$114 Roundtrip, found 5 hours ago

$114

Roundtrip

found 5 hours ago

Select Delta flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $114 found 5 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$121 Roundtrip, found 5 hours ago

$121

Roundtrip

found 5 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $121 found 5 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$124 Roundtrip, found 6 hours ago

$124

Roundtrip

found 6 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $124 found 6 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$126 Roundtrip, found 5 hours ago

$126

Roundtrip

found 5 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $126 found 5 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$131 Roundtrip, found 5 hours ago

$131

Roundtrip

found 5 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $131 found 5 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$135 Roundtrip, found 5 hours ago

$135

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $135 found 5 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$136 Roundtrip, found 5 hours ago

$136

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $136 found 5 hours ago

Tue, Jul 29 - Wed, Aug 6

ORD

O'Hare Intl.

LGA

LaGuardia

$136 Roundtrip, found 2 days ago

$136

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to LaGuardia, returning Wed, Aug 6, priced at $136 found 2 days ago

Wed, Sep 3 - Thu, Sep 4

ORD

O'Hare Intl.

EWR

Newark Liberty Intl. Airport

$137 Roundtrip, found 4 hours ago

$137

Roundtrip

found 4 hours ago

Select United flight, departing Wed, Sep 3 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Thu, Sep 4, priced at $137 found 4 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$137 Roundtrip, found 5 hours ago

$137

Roundtrip

found 5 hours ago

Select Delta flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $137 found 5 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$139 Roundtrip, found 6 hours ago

$139

Roundtrip

found 6 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $139 found 6 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$142 Roundtrip, found 5 hours ago

$142

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $142 found 5 hours ago

Wed, Sep 3 - Thu, Sep 4

ORD

O'Hare Intl.

EWR

Newark Liberty Intl. Airport

$142 Roundtrip, found 4 hours ago

$142

Roundtrip

found 4 hours ago

Select American Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Thu, Sep 4, priced at $142 found 4 hours ago

Wed, Aug 27 - Thu, Sep 4

ORD

O'Hare Intl.

EWR

Newark Liberty Intl. Airport

$144 Roundtrip, found 4 hours ago

$144

Roundtrip

found 4 hours ago

Select United flight, departing Wed, Aug 27 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Thu, Sep 4, priced at $144 found 4 hours ago

Wed, Aug 20 - Tue, Aug 26

ORD

O'Hare Intl.

LGA

LaGuardia

$146 Roundtrip, found 5 hours ago

$146

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to LaGuardia, returning Tue, Aug 26, priced at $146 found 5 hours ago

Wed, Aug 13 - Tue, Aug 19

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$157 Roundtrip, found 4 days ago

$157

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Wed, Aug 13 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Aug 19, priced at $157 found 4 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

EWR

Newark Liberty Intl. Airport

$264 Roundtrip, found 4 hours ago

$264

Roundtrip

found 4 hours ago

Select Frontier Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Wed, Sep 10, priced at $264 found 4 hours ago