Flights from Chicago to Cape Neddick

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.

Wed, Sep 3 - Tue, Sep 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$183 Roundtrip, found 6 hours ago

$183

Roundtrip

found 6 hours ago

Select JetBlue Airways flight, departing Wed, Sep 3 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 9, priced at $183 found 6 hours ago

Wed, Oct 8 - Wed, Oct 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$193 Roundtrip, found 20 hours ago

$193

Roundtrip

found 20 hours ago

Select JetBlue Airways flight, departing Wed, Oct 8 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Oct 15, priced at $193 found 20 hours ago

Sun, Oct 12 - Sat, Oct 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 20 hours ago

$210

Roundtrip

found 20 hours ago

Select JetBlue Airways flight, departing Sun, Oct 12 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 18, priced at $210 found 20 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 6 hours ago

$210

Roundtrip

found 6 hours ago

Select JetBlue Airways flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $210 found 6 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$217 Roundtrip, found 6 hours ago

$217

Roundtrip

found 6 hours ago

Select United flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $217 found 6 hours ago

Tue, Sep 30 - Sat, Oct 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$218 Roundtrip, found 1 day ago

$218

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Tue, Sep 30 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 4, priced at $218 found 1 day ago

Wed, Sep 3 - Fri, Sep 5

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$220 Roundtrip, found 6 hours ago

$220

Roundtrip

found 6 hours ago

Select JetBlue Airways flight, departing Wed, Sep 3 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 5, priced at $220 found 6 hours ago

Sat, Sep 6 - Tue, Sep 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$223 Roundtrip, found 6 hours ago

$223

Roundtrip

found 6 hours ago

Select JetBlue Airways flight, departing Sat, Sep 6 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 9, priced at $223 found 6 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$227 Roundtrip, found 6 hours ago

$227

Roundtrip

found 6 hours ago

Select United flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $227 found 6 hours ago

Sun, Aug 31 - Thu, Sep 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$228 Roundtrip, found 6 hours ago

$228

Roundtrip

found 6 hours ago

Select Delta flight, departing Sun, Aug 31 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Sep 4, priced at $228 found 6 hours ago

Sat, Oct 11 - Sat, Oct 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$228 Roundtrip, found 20 hours ago

$228

Roundtrip

found 20 hours ago

Select JetBlue Airways flight, departing Sat, Oct 11 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 18, priced at $228 found 20 hours ago

Wed, Sep 3 - Sun, Sep 7

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$231 Roundtrip, found 6 hours ago

$231

Roundtrip

found 6 hours ago

Select JetBlue Airways flight, departing Wed, Sep 3 from O'Hare Intl. to Portland Intl. Jetport, returning Sun, Sep 7, priced at $231 found 6 hours ago

Thu, Oct 9 - Sat, Oct 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$233 Roundtrip, found 20 hours ago

$233

Roundtrip

found 20 hours ago

Select JetBlue Airways flight, departing Thu, Oct 9 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 18, priced at $233 found 20 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$234 Roundtrip, found 6 hours ago

$234

Roundtrip

found 6 hours ago

Select American Airlines flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $234 found 6 hours ago

Wed, Sep 3 - Thu, Sep 11

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$237 Roundtrip, found 6 hours ago

$237

Roundtrip

found 6 hours ago

Select Delta flight, departing Wed, Sep 3 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Sep 11, priced at $237 found 6 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$238 Roundtrip, found 6 hours ago

$238

Roundtrip

found 6 hours ago

Select United flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $238 found 6 hours ago

Sat, Oct 11 - Wed, Oct 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$238 Roundtrip, found 20 hours ago

$238

Roundtrip

found 20 hours ago

Select JetBlue Airways flight, departing Sat, Oct 11 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Oct 15, priced at $238 found 20 hours ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$241 Roundtrip, found 6 hours ago

$241

Roundtrip

found 6 hours ago

Select JetBlue Airways flight, departing Thu, Sep 4 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 8, priced at $241 found 6 hours ago

Sun, Sep 7 - Tue, Sep 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$243 Roundtrip, found 6 hours ago

$243

Roundtrip

found 6 hours ago

Select JetBlue Airways flight, departing Sun, Sep 7 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 9, priced at $243 found 6 hours ago

Thu, Sep 4 - Sat, Sep 6

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$243 Roundtrip, found 6 hours ago

$243

Roundtrip

found 6 hours ago

Select JetBlue Airways flight, departing Thu, Sep 4 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 6, priced at $243 found 6 hours ago