Flights from Portland to Chicago

Cheapest flights from Portland

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 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$194 Roundtrip, found 1 day ago

$194

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $194 found 1 day ago

Tue, Jul 22 - Sat, Aug 16

PDX

Portland Intl.

ORD

O'Hare Intl.

$204 Roundtrip, found 1 day ago

$204

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Tue, Jul 22 from Portland Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $204 found 1 day ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$204 Roundtrip, found 1 day ago

$204

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $204 found 1 day ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$214 Roundtrip, found 1 day ago

$214

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $214 found 1 day ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$214 Roundtrip, found 1 day ago

$214

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $214 found 1 day ago

Mon, Jul 21 - Sat, Aug 16

PDX

Portland Intl.

ORD

O'Hare Intl.

$215 Roundtrip, found 1 day ago

$215

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Mon, Jul 21 from Portland Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $215 found 1 day ago

Tue, Jul 22 - Mon, Aug 18

PDX

Portland Intl.

ORD

O'Hare Intl.

$217 Roundtrip, found 1 day ago

$217

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Tue, Jul 22 from Portland Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $217 found 1 day ago

Mon, Jul 21 - Sun, Aug 17

PDX

Portland Intl.

ORD

O'Hare Intl.

$220 Roundtrip, found 1 day ago

$220

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Jul 21 from Portland Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $220 found 1 day ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$223 Roundtrip, found 1 day ago

$223

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $223 found 1 day ago

Wed, Jul 23 - Sun, Aug 17

PDX

Portland Intl.

ORD

O'Hare Intl.

$224 Roundtrip, found 1 day ago

$224

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $224 found 1 day ago

Thu, Jul 24 - Mon, Aug 18

PDX

Portland Intl.

ORD

O'Hare Intl.

$228 Roundtrip, found 1 day ago

$228

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Thu, Jul 24 from Portland Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $228 found 1 day ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$231 Roundtrip, found 1 day ago

$231

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $231 found 1 day ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$231 Roundtrip, found 1 day ago

$231

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $231 found 1 day ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$234 Roundtrip, found 1 day ago

$234

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $234 found 1 day ago

Sun, Jul 20 - Sat, Aug 16

PDX

Portland Intl.

ORD

O'Hare Intl.

$235 Roundtrip, found 1 day ago

$235

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Sun, Jul 20 from Portland Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $235 found 1 day ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 1 day ago

$240

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $240 found 1 day ago

Sun, Jul 20 - Mon, Aug 18

PDX

Portland Intl.

ORD

O'Hare Intl.

$248 Roundtrip, found 1 day ago

$248

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Sun, Jul 20 from Portland Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $248 found 1 day ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$249 Roundtrip, found 1 day ago

$249

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $249 found 1 day ago

Sun, Jul 20 - Sun, Aug 17

PDX

Portland Intl.

ORD

O'Hare Intl.

$255 Roundtrip, found 1 day ago

$255

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Sun, Jul 20 from Portland Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $255 found 1 day ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$256 Roundtrip, found 1 day ago

$256

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $256 found 1 day ago