Flights from Chicago to Ogunquit - Wells

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, Oct 8 - Sat, Oct 18

ORD

O'Hare Intl.

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Portland Intl. Jetport

$183 Roundtrip, found 6 hours ago

$183

Roundtrip

found 6 hours ago

Select JetBlue Airways flight, departing Wed, Oct 8 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 18, priced at $183 found 6 hours ago

Wed, Oct 8 - Wed, Oct 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$193 Roundtrip, found 6 hours ago

$193

Roundtrip

found 6 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 6 hours ago

Sun, Oct 12 - Sat, Oct 18

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 Sun, Oct 12 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 18, priced at $210 found 6 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 14 hours ago

$210

Roundtrip

found 14 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 14 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$217 Roundtrip, found 14 hours ago

$217

Roundtrip

found 14 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 14 hours ago

Tue, Sep 30 - Sat, Oct 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$218 Roundtrip, found 12 hours ago

$218

Roundtrip

found 12 hours 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 12 hours ago

Sun, Oct 12 - Wed, Oct 15

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 Sun, Oct 12 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Oct 15, priced at $220 found 6 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$227 Roundtrip, found 14 hours ago

$227

Roundtrip

found 14 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 14 hours ago

Sat, Oct 11 - Sat, Oct 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$228 Roundtrip, found 6 hours ago

$228

Roundtrip

found 6 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 6 hours ago

Mon, Sep 29 - Fri, Oct 3

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$231 Roundtrip, found 12 hours ago

$231

Roundtrip

found 12 hours 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 12 hours ago

Thu, Oct 9 - Sat, Oct 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$233 Roundtrip, found 6 hours ago

$233

Roundtrip

found 6 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 6 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$234 Roundtrip, found 14 hours ago

$234

Roundtrip

found 14 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 14 hours ago

Tue, Sep 30 - Wed, Oct 1

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$237 Roundtrip, found 12 hours ago

$237

Roundtrip

found 12 hours ago

Select Delta flight, departing Tue, Sep 30 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Oct 1, priced at $237 found 12 hours ago

Sat, Oct 11 - Wed, Oct 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$238 Roundtrip, found 6 hours ago

$238

Roundtrip

found 6 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 6 hours ago

Thu, Oct 9 - Wed, Oct 15

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, Oct 9 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Oct 15, priced at $243 found 6 hours ago

Thu, Oct 2 - Sat, Oct 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$243 Roundtrip, found 12 hours ago

$243

Roundtrip

found 12 hours ago

Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 4, priced at $243 found 12 hours ago

Tue, Sep 30 - Sun, Oct 5

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$244 Roundtrip, found 12 hours ago

$244

Roundtrip

found 12 hours ago

Select JetBlue Airways flight, departing Tue, Sep 30 from O'Hare Intl. to Portland Intl. Jetport, returning Sun, Oct 5, priced at $244 found 12 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$248 Roundtrip, found 14 hours ago

$248

Roundtrip

found 14 hours ago

Select American Airlines flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $248 found 14 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$250 Roundtrip, found 14 hours ago

$250

Roundtrip

found 14 hours ago

Select JetBlue Airways flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $250 found 14 hours ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$252 Roundtrip, found 14 hours ago

$252

Roundtrip

found 14 hours ago

Select American Airlines flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $252 found 14 hours ago