Flights from Chicago to New Gloucester

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.

Mon, Sep 15 - Sat, Sep 27

ORD

O'Hare Intl.

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Portland Intl. Jetport

$183 Roundtrip, found 21 hours ago

$183

Roundtrip

found 21 hours ago

Select JetBlue Airways flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $183 found 21 hours ago

Mon, Sep 15 - Mon, Sep 29

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 21 hours ago

$210

Roundtrip

found 21 hours ago

Select JetBlue Airways flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 29, priced at $210 found 21 hours ago

Sun, Sep 14 - Sat, Sep 27

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$233 Roundtrip, found 21 hours ago

$233

Roundtrip

found 21 hours ago

Select JetBlue Airways flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $233 found 21 hours ago

Wed, Sep 17 - Sat, Sep 27

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$246 Roundtrip, found 21 hours ago

$246

Roundtrip

found 21 hours ago

Select JetBlue Airways flight, departing Wed, Sep 17 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $246 found 21 hours ago

Tue, Sep 16 - Wed, Oct 1

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$251 Roundtrip, found 21 hours ago

$251

Roundtrip

found 21 hours ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Oct 1, priced at $251 found 21 hours ago

Tue, Sep 16 - Thu, Sep 25

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$253 Roundtrip, found 21 hours ago

$253

Roundtrip

found 21 hours ago

Select JetBlue Airways flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Sep 25, priced at $253 found 21 hours ago

Sun, Sep 14 - Mon, Sep 29

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$260 Roundtrip, found 21 hours ago

$260

Roundtrip

found 21 hours ago

Select JetBlue Airways flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 29, priced at $260 found 21 hours ago

Tue, Sep 16 - Fri, Sep 26

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$265 Roundtrip, found 21 hours ago

$265

Roundtrip

found 21 hours ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $265 found 21 hours ago

Wed, Sep 17 - Mon, Sep 29

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$273 Roundtrip, found 21 hours ago

$273

Roundtrip

found 21 hours ago

Select JetBlue Airways flight, departing Wed, Sep 17 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 29, priced at $273 found 21 hours ago

Mon, Sep 15 - Wed, Oct 1

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$277 Roundtrip, found 21 hours ago

$277

Roundtrip

found 21 hours ago

Select Delta flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Oct 1, priced at $277 found 21 hours ago

Sun, Sep 14 - Fri, Sep 26

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, found 21 hours ago

$279

Roundtrip

found 21 hours ago

Select Delta flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $279 found 21 hours ago

Tue, Sep 16 - Mon, Sep 29

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$280 Roundtrip, found 21 hours ago

$280

Roundtrip

found 21 hours ago

Select JetBlue Airways flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 29, priced at $280 found 21 hours ago

Thu, Sep 18 - Tue, Sep 30

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$315 Roundtrip, found 21 hours ago

$315

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 30, priced at $315 found 21 hours ago

Thu, Sep 18 - Sat, Sep 27

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$325 Roundtrip, found 21 hours ago

$325

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $325 found 21 hours ago

Thu, Sep 18 - Thu, Sep 25

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$329 Roundtrip, found 21 hours ago

$329

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Sep 25, priced at $329 found 21 hours ago

Tue, Sep 16 - Sun, Sep 28

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$339 Roundtrip, found 21 hours ago

$339

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Sun, Sep 28, priced at $339 found 21 hours ago

Wed, Sep 17 - Sun, Sep 28

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$349 Roundtrip, found 21 hours ago

$349

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Portland Intl. Jetport, returning Sun, Sep 28, priced at $349 found 21 hours ago

Sun, Sep 14 - Sun, Sep 28

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$353 Roundtrip, found 21 hours ago

$353

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Sun, Sep 28, priced at $353 found 21 hours ago