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.

Tue, Jul 22 - Wed, Jul 23

PDX

Portland Intl.

ORD

O'Hare Intl.

$188 Roundtrip, found 2 days ago

$188

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from Portland Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $188 found 2 days ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$194 Roundtrip, found 4 days ago

$194

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $194 found 4 days ago

Sun, Aug 31 - Wed, Sep 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$203 Roundtrip, found 3 days ago

$203

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Sun, Aug 31 from Portland Intl. to O'Hare Intl., returning Wed, Sep 3, priced at $203 found 3 days ago

Tue, Jul 22 - Sat, Aug 16

PDX

Portland Intl.

ORD

O'Hare Intl.

$204 Roundtrip, found 4 days ago

$204

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Tue, Jul 22 from Portland Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $204 found 4 days ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$204 Roundtrip, found 4 days ago

$204

Roundtrip

found 4 days ago

Select United flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $204 found 4 days ago

Mon, Jul 28 - Wed, Jul 30

PDX

Portland Intl.

ORD

O'Hare Intl.

$206 Roundtrip, found 2 days ago

$206

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jul 28 from Portland Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $206 found 2 days ago

Tue, Jul 29 - Wed, Jul 30

PDX

Portland Intl.

ORD

O'Hare Intl.

$209 Roundtrip, found 2 days ago

$209

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 29 from Portland Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $209 found 2 days ago

Tue, Aug 26 - Sun, Aug 31

PDX

Portland Intl.

ORD

O'Hare Intl.

$213 Roundtrip, found 3 days ago

$213

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Tue, Aug 26 from Portland Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $213 found 3 days ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$214 Roundtrip, found 4 days ago

$214

Roundtrip

found 4 days ago

Select Alaska Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $214 found 4 days ago

Thu, Aug 28 - Sun, Aug 31

PDX

Portland Intl.

ORD

O'Hare Intl.

$214 Roundtrip, found 3 days ago

$214

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Thu, Aug 28 from Portland Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $214 found 3 days ago

Thu, Aug 28 - Sun, Aug 31

PDX

Portland Intl.

ORD

O'Hare Intl.

$214 Roundtrip, found 3 days ago

$214

Roundtrip

found 3 days ago

Select American Airlines flight, departing Thu, Aug 28 from Portland Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $214 found 3 days ago

Mon, Jul 21 - Sat, Aug 16

PDX

Portland Intl.

ORD

O'Hare Intl.

$215 Roundtrip, found 4 days ago

$215

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Mon, Jul 21 from Portland Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $215 found 4 days ago

Tue, Jul 22 - Mon, Aug 18

PDX

Portland Intl.

ORD

O'Hare Intl.

$217 Roundtrip, found 4 days ago

$217

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Tue, Jul 22 from Portland Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $217 found 4 days ago

Mon, Jul 28 - Sat, Aug 2

PDX

Portland Intl.

ORD

O'Hare Intl.

$220 Roundtrip, found 2 days ago

$220

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jul 28 from Portland Intl. to O'Hare Intl., returning Sat, Aug 2, priced at $220 found 2 days ago

Wed, Jul 23 - Tue, Aug 19

PDX

Portland Intl.

ORD

O'Hare Intl.

$223 Roundtrip, found 4 days ago

$223

Roundtrip

found 4 days ago

Select Alaska Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $223 found 4 days ago

Wed, Jul 23 - Sun, Aug 17

PDX

Portland Intl.

ORD

O'Hare Intl.

$224 Roundtrip, found 4 days ago

$224

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Wed, Jul 23 from Portland Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $224 found 4 days ago

Thu, Aug 28 - Sun, Aug 31

PDX

Portland Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 3 days ago

$227

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Aug 28 from Portland Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $227 found 3 days ago

Sat, Jul 26 - Wed, Jul 30

PDX

Portland Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 2 days ago

$227

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Sat, Jul 26 from Portland Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $227 found 2 days ago

Fri, Jul 25 - Fri, Jul 25

PDX

Portland Intl.

ORD

O'Hare Intl.

$314 Roundtrip, found 2 days ago

$314

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Jul 25 from Portland Intl. to O'Hare Intl., returning Fri, Jul 25, priced at $314 found 2 days ago

Thu, Aug 28 - Sun, Aug 31

PDX

Portland Intl.

ORD

O'Hare Intl.

$330 Roundtrip, found 3 days ago

$330

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Aug 28 from Portland Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $330 found 3 days ago