Flights from Chicago to West Portland

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.

Thu, Jul 10 - Fri, Jul 18

ORD

O'Hare Intl.

PDX

Portland Intl.

$198 Roundtrip, found 6 hours ago

$198

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Thu, Jul 10 from O'Hare Intl. to Portland Intl., returning Fri, Jul 18, priced at $198 found 6 hours ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$200 Roundtrip, found 6 hours ago

$200

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $200 found 6 hours ago

Tue, Jul 8 - Tue, Jul 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$206 Roundtrip, found 6 hours ago

$206

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Portland Intl., returning Tue, Jul 15, priced at $206 found 6 hours ago

Wed, Jun 18 - Mon, Jun 23

ORD

O'Hare Intl.

PDX

Portland Intl.

$213 Roundtrip, found 2 days ago

$213

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Portland Intl., returning Mon, Jun 23, priced at $213 found 2 days ago

Tue, Jul 8 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$216 Roundtrip, found 6 hours ago

$216

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $216 found 6 hours ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$219 Roundtrip, found 6 hours ago

$219

Roundtrip

found 6 hours ago

Select American Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $219 found 6 hours ago

Thu, Jul 10 - Fri, Jul 18

ORD

O'Hare Intl.

PDX

Portland Intl.

$220 Roundtrip, found 6 hours ago

$220

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Thu, Jul 10 from O'Hare Intl. to Portland Intl., returning Fri, Jul 18, priced at $220 found 6 hours ago

Tue, Jun 17 - Fri, Jun 20

ORD

O'Hare Intl.

PDX

Portland Intl.

$226 Roundtrip, found 2 days ago

$226

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Portland Intl., returning Fri, Jun 20, priced at $226 found 2 days ago

Sat, Jul 12 - Tue, Jul 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$227 Roundtrip, found 6 hours ago

$227

Roundtrip

found 6 hours ago

Select Hawaiian Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Portland Intl., returning Tue, Jul 15, priced at $227 found 6 hours ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$229 Roundtrip, found 6 hours ago

$229

Roundtrip

found 6 hours ago

Select United flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $229 found 6 hours ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$234 Roundtrip, found 6 hours ago

$234

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $234 found 6 hours ago

Wed, Jun 18 - Mon, Jun 23

ORD

O'Hare Intl.

PDX

Portland Intl.

$236 Roundtrip, found 2 days ago

$236

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Portland Intl., returning Mon, Jun 23, priced at $236 found 2 days ago

Thu, Jul 10 - Fri, Jul 18

ORD

O'Hare Intl.

PDX

Portland Intl.

$238 Roundtrip, found 6 hours ago

$238

Roundtrip

found 6 hours ago

Select United flight, departing Thu, Jul 10 from O'Hare Intl. to Portland Intl., returning Fri, Jul 18, priced at $238 found 6 hours ago

Fri, Jul 11 - Tue, Jul 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$238 Roundtrip, found 6 hours ago

$238

Roundtrip

found 6 hours ago

Select Hawaiian Airlines flight, departing Fri, Jul 11 from O'Hare Intl. to Portland Intl., returning Tue, Jul 15, priced at $238 found 6 hours ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$238 Roundtrip, found 6 hours ago

$238

Roundtrip

found 6 hours ago

Select American Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $238 found 6 hours ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$238 Roundtrip, found 6 hours ago

$238

Roundtrip

found 6 hours ago

Select United flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $238 found 6 hours ago

Wed, Jun 18 - Mon, Jun 23

ORD

O'Hare Intl.

PDX

Portland Intl.

$243 Roundtrip, found 2 days ago

$243

Roundtrip

found 2 days ago

Select United flight, departing Wed, Jun 18 from O'Hare Intl. to Portland Intl., returning Mon, Jun 23, priced at $243 found 2 days ago

Sat, Aug 30 - Tue, Sep 9

MDW

Midway Intl.

PDX

Portland Intl.

$247 Roundtrip, found 3 days ago

$247

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Aug 30 from Midway Intl. to Portland Intl., returning Tue, Sep 9, priced at $247 found 3 days ago

Thu, Aug 28 - Sun, Sep 7

MDW

Midway Intl.

PDX

Portland Intl.

$248 Roundtrip, found 3 days ago

$248

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Aug 28 from Midway Intl. to Portland Intl., returning Sun, Sep 7, priced at $248 found 3 days ago

Thu, Jul 10 - Fri, Jul 18

ORD

O'Hare Intl.

PDX

Portland Intl.

$259 Roundtrip, found 6 hours ago

$259

Roundtrip

found 6 hours ago

Select Alaska Airlines flight, departing Thu, Jul 10 from O'Hare Intl. to Portland Intl., returning Fri, Jul 18, priced at $259 found 6 hours ago