Flights from Chicago to South Portland

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.

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Portland Intl. Jetport

$183 Roundtrip, found 5 days ago

$183

Roundtrip

found 5 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 5 days ago

Mon, Sep 15 - Tue, Sep 16

ORD

O'Hare Intl.

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Portland Intl. Jetport

$203 Roundtrip, found 5 days ago

$203

Roundtrip

found 5 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 5 days ago

Sun, Sep 14 - Tue, Sep 16

ORD

O'Hare Intl.

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Portland Intl. Jetport

$208 Roundtrip, found 5 days ago

$208

Roundtrip

found 5 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 5 days ago

Sat, Sep 13 - Sat, Sep 20

ORD

O'Hare Intl.

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Portland Intl. Jetport

$222 Roundtrip, found 5 days ago

$222

Roundtrip

found 5 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 5 days ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

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Portland Intl. Jetport

$233 Roundtrip, found 5 days ago

$233

Roundtrip

found 5 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 5 days ago

Sun, Sep 14 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$248 Roundtrip, found 5 days ago

$248

Roundtrip

found 5 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 5 days ago

Tue, Sep 16 - Tue, Sep 16

ORD

O'Hare Intl.

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Portland Intl. Jetport

$251 Roundtrip, found 5 days ago

$251

Roundtrip

found 5 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 5 days ago

Mon, Sep 15 - Sat, Sep 20

ORD

O'Hare Intl.

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Portland Intl. Jetport

$253 Roundtrip, found 5 days ago

$253

Roundtrip

found 5 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 5 days ago

Sun, Sep 14 - Wed, Sep 17

ORD

O'Hare Intl.

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Portland Intl. Jetport

$265 Roundtrip, found 5 days ago

$265

Roundtrip

found 5 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 5 days ago

Mon, Sep 15 - Wed, Sep 17

ORD

O'Hare Intl.

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Portland Intl. Jetport

$287 Roundtrip, found 5 days ago

$287

Roundtrip

found 5 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 5 days ago

Sat, Sep 13 - Fri, Sep 19

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$287 Roundtrip, found 5 days ago

$287

Roundtrip

found 5 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 5 days ago

Tue, Sep 16 - Thu, Sep 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$315 Roundtrip, found 5 days ago

$315

Roundtrip

found 5 days ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Sep 18, priced at $315 found 5 days ago