Flights from Chicago to 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.

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$198 Roundtrip, found 14 hours ago

$198

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $198 found 14 hours ago

Mon, Jul 7 - Mon, Jul 14

ORD

O'Hare Intl.

PDX

Portland Intl.

$206 Roundtrip, found 3 days ago

$206

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Mon, Jul 7 from O'Hare Intl. to Portland Intl., returning Mon, Jul 14, priced at $206 found 3 days ago

Mon, Jul 7 - Wed, Jul 16

ORD

O'Hare Intl.

PDX

Portland Intl.

$216 Roundtrip, found 3 days ago

$216

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Mon, Jul 7 from O'Hare Intl. to Portland Intl., returning Wed, Jul 16, priced at $216 found 3 days ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$218 Roundtrip, found 14 hours ago

$218

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $218 found 14 hours ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$219 Roundtrip, found 14 hours ago

$219

Roundtrip

found 14 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 14 hours ago

Fri, Jul 11 - Wed, Jul 16

ORD

O'Hare Intl.

PDX

Portland Intl.

$226 Roundtrip, found 3 days ago

$226

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Fri, Jul 11 from O'Hare Intl. to Portland Intl., returning Wed, Jul 16, priced at $226 found 3 days ago

Sat, Jul 12 - Tue, Jul 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$227 Roundtrip, found 3 days ago

$227

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Portland Intl., returning Tue, Jul 15, priced at $227 found 3 days ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$229 Roundtrip, found 14 hours ago

$229

Roundtrip

found 14 hours ago

Select United flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $229 found 14 hours ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$232 Roundtrip, found 14 hours ago

$232

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $232 found 14 hours ago

Sat, Jul 12 - Mon, Jul 14

ORD

O'Hare Intl.

PDX

Portland Intl.

$238 Roundtrip, found 3 days ago

$238

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Portland Intl., returning Mon, Jul 14, priced at $238 found 3 days ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$238 Roundtrip, found 14 hours ago

$238

Roundtrip

found 14 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 14 hours ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$243 Roundtrip, found 14 hours ago

$243

Roundtrip

found 14 hours ago

Select American Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $243 found 14 hours ago

Sat, Aug 30 - Tue, Sep 9

MDW

Midway Intl.

PDX

Portland Intl.

$247 Roundtrip, found 11 hours ago

$247

Roundtrip

found 11 hours ago

Select Delta flight, departing Sat, Aug 30 from Midway Intl. to Portland Intl., returning Tue, Sep 9, priced at $247 found 11 hours ago

Sat, Jul 12 - Wed, Jul 16

ORD

O'Hare Intl.

PDX

Portland Intl.

$247 Roundtrip, found 3 days ago

$247

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Portland Intl., returning Wed, Jul 16, priced at $247 found 3 days ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$248 Roundtrip, found 14 hours ago

$248

Roundtrip

found 14 hours ago

Select United flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $248 found 14 hours ago

Thu, Aug 28 - Sun, Sep 7

MDW

Midway Intl.

PDX

Portland Intl.

$248 Roundtrip, found 11 hours ago

$248

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Thu, Aug 28 from Midway Intl. to Portland Intl., returning Sun, Sep 7, priced at $248 found 11 hours ago

Thu, Jul 10 - Fri, Jul 18

ORD

O'Hare Intl.

PDX

Portland Intl.

$249 Roundtrip, found 5 days ago

$249

Roundtrip

found 5 days ago

Select Hawaiian Airlines flight, departing Thu, Jul 10 from O'Hare Intl. to Portland Intl., returning Fri, Jul 18, priced at $249 found 5 days ago

Sat, Jun 28 - Mon, Jul 7

ORD

O'Hare Intl.

PDX

Portland Intl.

$250 Roundtrip, found 6 days ago

$250

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Portland Intl., returning Mon, Jul 7, priced at $250 found 6 days ago

Thu, Jun 26 - Sat, Jul 5

MDW

Midway Intl.

PDX

Portland Intl.

$254 Roundtrip, found 6 days ago

$254

Roundtrip

found 6 days ago

Select Delta flight, departing Thu, Jun 26 from Midway Intl. to Portland Intl., returning Sat, Jul 5, priced at $254 found 6 days ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$258 Roundtrip, found 14 hours ago

$258

Roundtrip

found 14 hours ago

Select Alaska Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $258 found 14 hours ago