$87 Cheap Flights from Chicago (CHI) to Portland (PWM)

Cheap Flights from Chicago to Portland (CHI-PWM)

Prices were available within the past 7 days and start at $87 for one-way flights and $173 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Sep 16 - Tue, Sep 22

ORD

Chicago

PWM

Portland

$173 Roundtrip, found 2 hours ago

$173

Roundtrip

found 2 hours ago

Select United flight, departing Wed, Sep 16 from Chicago to Portland, returning Tue, Sep 22, priced at $173 found 2 hours ago

Wed, Sep 9 - Tue, Sep 15

MDW

Chicago

PWM

Portland

$174 Roundtrip, found 1 day ago

$174

Roundtrip

found 1 day ago

Select Southwest Airlines flight, departing Wed, Sep 9 from Chicago to Portland, returning Tue, Sep 15, priced at $174 found 1 day ago

Tue, Sep 8 - Sat, Sep 12

MDW

Chicago

PWM

Portland

$192 Roundtrip, found 21 hours ago

$192

Roundtrip

found 21 hours ago

Select Southwest Airlines flight, departing Tue, Sep 8 from Chicago to Portland, returning Sat, Sep 12, priced at $192 found 21 hours ago

Wed, Sep 9 - Tue, Sep 15

MDW

Chicago

PWM

Portland

$196 Roundtrip, found 1 day ago

$196

Roundtrip

found 1 day ago

Select Southwest Airlines flight, departing Wed, Sep 9 from Chicago to Portland, returning Tue, Sep 15, priced at $196 found 1 day ago

Wed, Sep 16 - Tue, Sep 22

ORD

Chicago

PWM

Portland

$197 Roundtrip, found 1 hour ago

$197

Roundtrip

found 1 hour ago

Select Delta flight, departing Wed, Sep 16 from Chicago to Portland, returning Tue, Sep 22, priced at $197 found 1 hour ago

Sat, May 23 - Tue, May 26

ORD

Chicago

PWM

Portland

$201 Roundtrip, found 8 hours ago

$201

Roundtrip

found 8 hours ago

Select United flight, departing Sat, May 23 from Chicago to Portland, returning Tue, May 26, priced at $201 found 8 hours ago

Fri, Jun 5 - Tue, Jun 9

MDW

Chicago

PWM

Portland

$210 Roundtrip, found 1 day ago

$210

Roundtrip

found 1 day ago

Select Southwest Airlines flight, departing Fri, Jun 5 from Chicago to Portland, returning Tue, Jun 9, priced at $210 found 1 day ago

Sat, May 23 - Tue, May 26

ORD

Chicago

PWM

Portland

$211 Roundtrip, found 8 hours ago

$211

Roundtrip

found 8 hours ago

Select United flight, departing Sat, May 23 from Chicago to Portland, returning Tue, May 26, priced at $211 found 8 hours ago

Wed, Sep 16 - Tue, Sep 22

ORD

Chicago

PWM

Portland

$233 Roundtrip, found 1 hour ago

$233

Roundtrip

found 1 hour ago

Select American Airlines flight, departing Wed, Sep 16 from Chicago to Portland, returning Tue, Sep 22, priced at $233 found 1 hour ago

Fri, Jun 12 - Tue, Jun 16

ORD

Chicago

PWM

Portland

$323 Roundtrip, found 1 day ago

$323

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Fri, Jun 12 from Chicago to Portland, returning Tue, Jun 16, priced at $323 found 1 day ago