Flights from Chicago to Long 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.

Fri, Sep 12 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$183 Roundtrip, found 2 days ago

$183

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, Sep 12 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $183 found 2 days ago

Mon, Sep 15 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$203 Roundtrip, found 2 days ago

$203

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $203 found 2 days ago

Sun, Sep 14 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$208 Roundtrip, found 2 days ago

$208

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $208 found 2 days ago

Tue, Jul 15 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$220 Roundtrip, found 4 days ago

$220

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Tue, Jul 15 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $220 found 4 days ago

Sat, Sep 13 - Sat, Sep 20

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$222 Roundtrip, found 2 days ago

$222

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sat, Sep 13 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 20, priced at $222 found 2 days ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$233 Roundtrip, found 2 days ago

$233

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $233 found 2 days ago

Sun, Sep 14 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$248 Roundtrip, found 2 days ago

$248

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $248 found 2 days ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$248 Roundtrip, found 4 days ago

$248

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $248 found 4 days ago

Tue, Sep 16 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$251 Roundtrip, found 2 days ago

$251

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $251 found 2 days ago

Mon, Sep 15 - Sat, Sep 20

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$253 Roundtrip, found 2 days ago

$253

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 20, priced at $253 found 2 days ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, found 4 days ago

$259

Roundtrip

found 4 days ago

Select United flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $259 found 4 days ago

Sun, Sep 14 - Wed, Sep 17

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$265 Roundtrip, found 2 days ago

$265

Roundtrip

found 2 days ago

Select Delta flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Sep 17, priced at $265 found 2 days ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$269 Roundtrip, found 4 days ago

$269

Roundtrip

found 4 days ago

Select American Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $269 found 4 days ago

Mon, Jul 14 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$275 Roundtrip, found 4 days ago

$275

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Mon, Jul 14 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $275 found 4 days ago

Mon, Jul 14 - Fri, Jul 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, found 4 days ago

$279

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Jul 14 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Jul 18, priced at $279 found 4 days ago

Sun, Jul 13 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, found 4 days ago

$279

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Sun, Jul 13 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $279 found 4 days ago

Mon, Sep 15 - Wed, Sep 17

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$287 Roundtrip, found 2 days ago

$287

Roundtrip

found 2 days ago

Select Delta flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Sep 17, priced at $287 found 2 days ago

Sat, Sep 13 - Fri, Sep 19

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$287 Roundtrip, found 2 days ago

$287

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Sep 13 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 19, priced at $287 found 2 days ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$288 Roundtrip, found 4 days ago

$288

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $288 found 4 days ago

Wed, Sep 17 - Sun, Sep 21

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$458 Roundtrip, found 4 days ago

$458

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Sep 17 from Midway Intl. to Portland Intl. Jetport, returning Sun, Sep 21, priced at $458 found 4 days ago