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

Tue, Jul 22 - Tue, Jul 29

PDX

Portland Intl.

ORD

O'Hare Intl.

$206 Roundtrip, found 6 days ago

$206

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from Portland Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $206 found 6 days 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 - Thu, Jul 31

PDX

Portland Intl.

ORD

O'Hare Intl.

$216 Roundtrip, found 6 days ago

$216

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from Portland Intl. to O'Hare Intl., returning Thu, Jul 31, priced at $216 found 6 days 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

Sat, Jul 26 - Tue, Jul 29

PDX

Portland Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 6 days ago

$227

Roundtrip

found 6 days ago

Select Hawaiian Airlines flight, departing Sat, Jul 26 from Portland Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $227 found 6 days 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

Tue, Jul 22 - Tue, Jul 22

PDX

Portland Intl.

ORD

O'Hare Intl.

$247 Roundtrip, found 6 days ago

$247

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Jul 22 from Portland Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $247 found 6 days 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 27 - Sat, Aug 2

PDX

Portland Intl.

ORD

O'Hare Intl.

$280 Roundtrip, found 6 days ago

$280

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sun, Jul 27 from Portland Intl. to O'Hare Intl., returning Sat, Aug 2, priced at $280 found 6 days ago