Flights from Chicago to West Ossipee

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 29 - Thu, Oct 2

ORD

O'Hare Intl.

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Portland Intl. Jetport

$183 Roundtrip, found 1 day ago

$183

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Oct 2, priced at $183 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$201 Roundtrip, found 1 day ago

$201

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $201 found 1 day ago

Mon, Sep 29 - Tue, Sep 30

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$203 Roundtrip, found 1 day ago

$203

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 30, priced at $203 found 1 day ago

Fri, Sep 26 - Tue, Sep 30

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 1 day ago

$210

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Fri, Sep 26 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 30, priced at $210 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$211 Roundtrip, found 1 day ago

$211

Roundtrip

found 1 day ago

Select United flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $211 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$217 Roundtrip, found 1 day ago

$217

Roundtrip

found 1 day ago

Select United flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $217 found 1 day ago

Tue, Sep 30 - Wed, Oct 1

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$219 Roundtrip, found 1 day ago

$219

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Sep 30 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Oct 1, priced at $219 found 1 day ago

Thu, Oct 2 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$220 Roundtrip, found 1 day ago

$220

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $220 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$227 Roundtrip, found 1 day ago

$227

Roundtrip

found 1 day ago

Select United flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $227 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$229 Roundtrip, found 1 day ago

$229

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $229 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$229 Roundtrip, found 1 day ago

$229

Roundtrip

found 1 day ago

Select United flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $229 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$231 Roundtrip, found 1 day ago

$231

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $231 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$231 Roundtrip, found 1 day ago

$231

Roundtrip

found 1 day ago

Select United flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $231 found 1 day ago

Mon, Sep 29 - Sun, Oct 5

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$233 Roundtrip, found 1 day ago

$233

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Sun, Oct 5, priced at $233 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$236 Roundtrip, found 1 day ago

$236

Roundtrip

found 1 day ago

Select United flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $236 found 1 day ago

Sun, Sep 28 - Thu, Oct 2

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$238 Roundtrip, found 1 day ago

$238

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sun, Sep 28 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Oct 2, priced at $238 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$239 Roundtrip, found 1 day ago

$239

Roundtrip

found 1 day ago

Select United flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $239 found 1 day ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$241 Roundtrip, found 1 day ago

$241

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Oct 3, priced at $241 found 1 day ago

Tue, Sep 30 - Tue, Oct 7

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$241 Roundtrip, found 6 days ago

$241

Roundtrip

found 6 days ago

Select American Airlines flight, departing Tue, Sep 30 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Oct 7, priced at $241 found 6 days ago

Tue, Sep 30 - Tue, Oct 7

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$245 Roundtrip, found 6 days ago

$245

Roundtrip

found 6 days ago

Select American Airlines flight, departing Tue, Sep 30 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Oct 7, priced at $245 found 6 days ago