$97 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 $97 for one-way flights and $174 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Sep 9 - Tue, Sep 15

MDW

Chicago

PWM

Portland

$174 Roundtrip, found 1 hour ago

$174

Roundtrip

found 1 hour ago

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

Wed, Sep 9 - Tue, Sep 15

MDW

Chicago

PWM

Portland

$196 Roundtrip, found 1 hour ago

$196

Roundtrip

found 1 hour ago

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

Fri, Jun 5 - Tue, Jun 9

MDW

Chicago

PWM

Portland

$210 Roundtrip, just found

$210

Roundtrip

just found

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

Fri, Jun 5 - Tue, Jun 9

MDW

Chicago

PWM

Portland

$220 Roundtrip, just found

$220

Roundtrip

just found

Select Southwest Airlines flight, departing Fri, Jun 5 from Chicago to Portland, returning Tue, Jun 9, priced at $220 just found

Fri, Jun 5 - Tue, Jun 9

MDW

Chicago

PWM

Portland

$225 Roundtrip, just found

$225

Roundtrip

just found

Select Southwest Airlines flight, departing Fri, Jun 5 from Chicago to Portland, returning Tue, Jun 9, priced at $225 just found

Mon, Aug 24 - Fri, Aug 28

MDW

Chicago

PWM

Portland

$228 Roundtrip, found 8 hours ago

$228

Roundtrip

found 8 hours ago

Select Southwest Airlines flight, departing Mon, Aug 24 from Chicago to Portland, returning Fri, Aug 28, priced at $228 found 8 hours ago

Fri, May 29 - Mon, Jun 1

RFD

Rockford

PWM

Portland

$268 Roundtrip, found 16 hours ago

$268

Roundtrip

found 16 hours ago

Select American Airlines flight, departing Fri, May 29 from Rockford to Portland, returning Mon, Jun 1, priced at $268 found 16 hours ago

Tue, Jun 9 - Wed, Jun 17

ORD

Chicago

PWM

Portland

$269 Roundtrip, just found

$269

Roundtrip

just found

Select United flight, departing Tue, Jun 9 from Chicago to Portland, returning Wed, Jun 17, priced at $269 just found

Fri, Jun 5 - Tue, Jun 9

ORD

Chicago

PWM

Portland

$289 Roundtrip, just found

$289

Roundtrip

just found

Select Delta flight, departing Fri, Jun 5 from Chicago to Portland, returning Tue, Jun 9, priced at $289 just found

Fri, Jun 12 - Tue, Jun 16

ORD

Chicago

PWM

Portland

$323 Roundtrip, found 5 hours ago

$323

Roundtrip

found 5 hours ago

Select JetBlue Airways flight, departing Fri, Jun 12 from Chicago to Portland, returning Tue, Jun 16, priced at $323 found 5 hours ago