Flights from Chicago to Wells Beach

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.

Sun, Sep 28 - Tue, Oct 7

ORD

O'Hare Intl.

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Portland Intl. Jetport

$183 Roundtrip, found 1 hour ago

$183

Roundtrip

found 1 hour ago

Select JetBlue Airways flight, departing Sun, Sep 28 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Oct 7, priced at $183 found 1 hour ago

Wed, Oct 8 - Wed, Oct 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$193 Roundtrip, found 5 days ago

$193

Roundtrip

found 5 days 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 5 days ago

Sat, Sep 27 - Sat, Oct 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$202 Roundtrip, found 1 hour ago

$202

Roundtrip

found 1 hour ago

Select United flight, departing Sat, Sep 27 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 4, priced at $202 found 1 hour ago

Mon, Sep 29 - Tue, Oct 7

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 1 hour ago

$210

Roundtrip

found 1 hour ago

Select JetBlue Airways flight, departing Mon, Sep 29 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Oct 7, priced at $210 found 1 hour ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 5 days ago

$210

Roundtrip

found 5 days 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 5 days ago

Sat, Sep 27 - Sat, Oct 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$216 Roundtrip, found 1 hour ago

$216

Roundtrip

found 1 hour ago

Select United flight, departing Sat, Sep 27 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 4, priced at $216 found 1 hour ago

Sat, Sep 27 - Sat, Oct 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$217 Roundtrip, found 1 hour ago

$217

Roundtrip

found 1 hour ago

Select Delta flight, departing Sat, Sep 27 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 4, priced at $217 found 1 hour ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select United flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $217 found 5 days ago

Tue, Sep 30 - Sat, Oct 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$218 Roundtrip, found 5 days ago

$218

Roundtrip

found 5 days 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 5 days ago

Wed, Sep 3 - Fri, Sep 5

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$220 Roundtrip, found 5 days ago

$220

Roundtrip

found 5 days 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 5 days ago

Sat, Sep 27 - Sat, Oct 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$220 Roundtrip, found 1 hour ago

$220

Roundtrip

found 1 hour ago

Select United flight, departing Sat, Sep 27 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 4, priced at $220 found 1 hour ago

Sat, Sep 6 - Tue, Sep 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$223 Roundtrip, found 5 days ago

$223

Roundtrip

found 5 days 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 5 days ago

Fri, Sep 26 - Thu, Oct 2

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$225 Roundtrip, found 1 hour ago

$225

Roundtrip

found 1 hour ago

Select Delta flight, departing Fri, Sep 26 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Oct 2, priced at $225 found 1 hour ago

Sat, Sep 27 - Sat, Oct 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$226 Roundtrip, found 1 hour ago

$226

Roundtrip

found 1 hour ago

Select United flight, departing Sat, Sep 27 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 4, priced at $226 found 1 hour ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$227 Roundtrip, found 5 days ago

$227

Roundtrip

found 5 days ago

Select United flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $227 found 5 days ago

Sat, Oct 11 - Sat, Oct 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$228 Roundtrip, found 5 days ago

$228

Roundtrip

found 5 days 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 5 days ago

Wed, Sep 3 - Sun, Sep 7

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$231 Roundtrip, found 5 days ago

$231

Roundtrip

found 5 days 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 5 days ago

Thu, Oct 9 - Sat, Oct 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$233 Roundtrip, found 5 days ago

$233

Roundtrip

found 5 days 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 5 days ago

Sat, Sep 27 - Sat, Oct 4

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$234 Roundtrip, found 1 hour ago

$234

Roundtrip

found 1 hour ago

Select American Airlines flight, departing Sat, Sep 27 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Oct 4, priced at $234 found 1 hour ago

Sat, Sep 27 - Tue, Oct 7

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$234 Roundtrip, found 1 hour ago

$234

Roundtrip

found 1 hour ago

Select JetBlue Airways flight, departing Sat, Sep 27 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Oct 7, priced at $234 found 1 hour ago