Flights from Chicago to Hamptons

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, Sep 20 - Tue, Sep 23

ORD

O'Hare Intl.

LGA

LaGuardia

$100 Roundtrip, found 4 days ago

$100

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Sep 20 from O'Hare Intl. to LaGuardia, returning Tue, Sep 23, priced at $100 found 4 days ago

Tue, Sep 23 - Sat, Sep 27

ORD

O'Hare Intl.

LGA

LaGuardia

$110 Roundtrip, found 4 days ago

$110

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Sep 23 from O'Hare Intl. to LaGuardia, returning Sat, Sep 27, priced at $110 found 4 days ago

Sat, Sep 20 - Tue, Sep 23

ORD

O'Hare Intl.

LGA

LaGuardia

$119 Roundtrip, found 4 days ago

$119

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Sep 20 from O'Hare Intl. to LaGuardia, returning Tue, Sep 23, priced at $119 found 4 days ago

Tue, Sep 9 - Sat, Sep 13

ORD

O'Hare Intl.

LGA

LaGuardia

$120 Roundtrip, found 6 hours ago

$120

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Tue, Sep 9 from O'Hare Intl. to LaGuardia, returning Sat, Sep 13, priced at $120 found 6 hours ago

Sat, Sep 20 - Tue, Sep 23

ORD

O'Hare Intl.

LGA

LaGuardia

$124 Roundtrip, found 4 days ago

$124

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Sep 20 from O'Hare Intl. to LaGuardia, returning Tue, Sep 23, priced at $124 found 4 days ago

Thu, Sep 25 - Sat, Sep 27

ORD

O'Hare Intl.

LGA

LaGuardia

$125 Roundtrip, found 4 days ago

$125

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Sep 25 from O'Hare Intl. to LaGuardia, returning Sat, Sep 27, priced at $125 found 4 days ago

Tue, Sep 2 - Sun, Sep 7

ORD

O'Hare Intl.

LGA

LaGuardia

$128 Roundtrip, found 2 days ago

$128

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to LaGuardia, returning Sun, Sep 7, priced at $128 found 2 days ago

Sat, Sep 20 - Tue, Sep 23

ORD

O'Hare Intl.

LGA

LaGuardia

$129 Roundtrip, found 4 days ago

$129

Roundtrip

found 4 days ago

Select United flight, departing Sat, Sep 20 from O'Hare Intl. to LaGuardia, returning Tue, Sep 23, priced at $129 found 4 days ago

Thu, Sep 11 - Fri, Sep 12

ORD

O'Hare Intl.

LGA

LaGuardia

$130 Roundtrip, found 6 hours ago

$130

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Thu, Sep 11 from O'Hare Intl. to LaGuardia, returning Fri, Sep 12, priced at $130 found 6 hours ago

Wed, Sep 10 - Sun, Sep 14

ORD

O'Hare Intl.

LGA

LaGuardia

$132 Roundtrip, found 4 days ago

$132

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Sep 10 from O'Hare Intl. to LaGuardia, returning Sun, Sep 14, priced at $132 found 4 days ago

Sun, Sep 21 - Wed, Sep 24

ORD

O'Hare Intl.

LGA

LaGuardia

$134 Roundtrip, found 4 days ago

$134

Roundtrip

found 4 days ago

Select United flight, departing Sun, Sep 21 from O'Hare Intl. to LaGuardia, returning Wed, Sep 24, priced at $134 found 4 days ago

Wed, Sep 24 - Sat, Sep 27

ORD

O'Hare Intl.

LGA

LaGuardia

$138 Roundtrip, found 4 days ago

$138

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Sep 24 from O'Hare Intl. to LaGuardia, returning Sat, Sep 27, priced at $138 found 4 days ago

Mon, Sep 8 - Thu, Sep 11

ORD

O'Hare Intl.

LGA

LaGuardia

$140 Roundtrip, found 6 hours ago

$140

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Mon, Sep 8 from O'Hare Intl. to LaGuardia, returning Thu, Sep 11, priced at $140 found 6 hours ago

Sat, Sep 20 - Tue, Sep 23

ORD

O'Hare Intl.

LGA

LaGuardia

$141 Roundtrip, found 4 days ago

$141

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Sep 20 from O'Hare Intl. to LaGuardia, returning Tue, Sep 23, priced at $141 found 4 days ago

Wed, Sep 3 - Tue, Sep 9

ORD

O'Hare Intl.

LGA

LaGuardia

$147 Roundtrip, found 2 days ago

$147

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Sep 3 from O'Hare Intl. to LaGuardia, returning Tue, Sep 9, priced at $147 found 2 days ago

Sat, Sep 20 - Tue, Sep 23

ORD

O'Hare Intl.

EWR

Newark Liberty Intl. Airport

$147 Roundtrip, found 4 days ago

$147

Roundtrip

found 4 days ago

Select United flight, departing Sat, Sep 20 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Tue, Sep 23, priced at $147 found 4 days ago

Sat, Sep 20 - Tue, Sep 23

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$147 Roundtrip, found 4 days ago

$147

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Sep 20 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Sep 23, priced at $147 found 4 days ago

Tue, Sep 23 - Sun, Sep 28

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$172 Roundtrip, found 4 days ago

$172

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Tue, Sep 23 from O'Hare Intl. to John F. Kennedy Intl., returning Sun, Sep 28, priced at $172 found 4 days ago

Sat, Sep 20 - Tue, Sep 23

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$174 Roundtrip, found 4 days ago

$174

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Sep 20 from O'Hare Intl. to John F. Kennedy Intl., returning Tue, Sep 23, priced at $174 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

EWR

Newark Liberty Intl. Airport

$212 Roundtrip, found 4 days ago

$212

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Sep 26 from Midway Intl. to Newark Liberty Intl. Airport, returning Sun, Sep 28, priced at $212 found 4 days ago