Flights from Chicago to Cannon Beach

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, May 29 - Thu, Jun 5

ORD

O'Hare Intl.

PDX

Portland Intl.

$175 Roundtrip, found 3 days ago

$175

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, May 29 from O'Hare Intl. to Portland Intl., returning Thu, Jun 5, priced at $175 found 3 days ago

Thu, May 29 - Thu, Jun 5

ORD

O'Hare Intl.

PDX

Portland Intl.

$178 Roundtrip, found 3 days ago

$178

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, May 29 from O'Hare Intl. to Portland Intl., returning Thu, Jun 5, priced at $178 found 3 days ago

Thu, May 29 - Thu, Jun 5

ORD

O'Hare Intl.

PDX

Portland Intl.

$184 Roundtrip, found 3 days ago

$184

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, May 29 from O'Hare Intl. to Portland Intl., returning Thu, Jun 5, priced at $184 found 3 days ago

Thu, May 29 - Thu, Jun 5

ORD

O'Hare Intl.

PDX

Portland Intl.

$205 Roundtrip, found 3 days ago

$205

Roundtrip

found 3 days ago

Select United flight, departing Thu, May 29 from O'Hare Intl. to Portland Intl., returning Thu, Jun 5, priced at $205 found 3 days ago

Fri, May 30 - Tue, Jun 3

ORD

O'Hare Intl.

PDX

Portland Intl.

$205 Roundtrip, found 3 days ago

$205

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Fri, May 30 from O'Hare Intl. to Portland Intl., returning Tue, Jun 3, priced at $205 found 3 days ago

Tue, Jul 8 - Thu, Jul 10

ORD

O'Hare Intl.

PDX

Portland Intl.

$206 Roundtrip, found 1 day ago

$206

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Portland Intl., returning Thu, Jul 10, priced at $206 found 1 day ago

Tue, Jul 1 - Fri, Jul 11

ORD

O'Hare Intl.

PDX

Portland Intl.

$213 Roundtrip, found 1 day ago

$213

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to Portland Intl., returning Fri, Jul 11, priced at $213 found 1 day ago

Tue, Jul 1 - Fri, Jul 11

ORD

O'Hare Intl.

PDX

Portland Intl.

$215 Roundtrip, found 1 day ago

$215

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to Portland Intl., returning Fri, Jul 11, priced at $215 found 1 day ago

Thu, Jul 10 - Wed, Jul 16

ORD

O'Hare Intl.

PDX

Portland Intl.

$218 Roundtrip, found 2 days ago

$218

Roundtrip

found 2 days ago

Select Alaska Airlines flight, departing Thu, Jul 10 from O'Hare Intl. to Portland Intl., returning Wed, Jul 16, priced at $218 found 2 days ago

Wed, May 28 - Sun, Jun 8

ORD

O'Hare Intl.

PDX

Portland Intl.

$218 Roundtrip, found 3 days ago

$218

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Wed, May 28 from O'Hare Intl. to Portland Intl., returning Sun, Jun 8, priced at $218 found 3 days ago

Thu, May 29 - Thu, Jun 5

ORD

O'Hare Intl.

PDX

Portland Intl.

$220 Roundtrip, found 3 days ago

$220

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, May 29 from O'Hare Intl. to Portland Intl., returning Thu, Jun 5, priced at $220 found 3 days ago

Wed, Jul 2 - Sun, Jul 6

ORD

O'Hare Intl.

PDX

Portland Intl.

$222 Roundtrip, found 3 days ago

$222

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Jul 2 from O'Hare Intl. to Portland Intl., returning Sun, Jul 6, priced at $222 found 3 days ago

Fri, Jul 4 - Tue, Jul 8

ORD

O'Hare Intl.

PDX

Portland Intl.

$223 Roundtrip, found 3 days ago

$223

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Fri, Jul 4 from O'Hare Intl. to Portland Intl., returning Tue, Jul 8, priced at $223 found 3 days ago

Tue, Jul 1 - Fri, Jul 11

ORD

O'Hare Intl.

PDX

Portland Intl.

$224 Roundtrip, found 1 day ago

$224

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 1 from O'Hare Intl. to Portland Intl., returning Fri, Jul 11, priced at $224 found 1 day ago

Wed, Jul 9 - Wed, Jul 9

ORD

O'Hare Intl.

PDX

Portland Intl.

$227 Roundtrip, found 1 day ago

$227

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Wed, Jul 9, priced at $227 found 1 day ago

Thu, May 29 - Thu, Jun 5

ORD

O'Hare Intl.

PDX

Portland Intl.

$228 Roundtrip, found 3 days ago

$228

Roundtrip

found 3 days ago

Select United flight, departing Thu, May 29 from O'Hare Intl. to Portland Intl., returning Thu, Jun 5, priced at $228 found 3 days ago

Tue, Jul 1 - Fri, Jul 11

ORD

O'Hare Intl.

PDX

Portland Intl.

$234 Roundtrip, found 1 day ago

$234

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 1 from O'Hare Intl. to Portland Intl., returning Fri, Jul 11, priced at $234 found 1 day ago

Thu, Jul 10 - Wed, Jul 16

ORD

O'Hare Intl.

PDX

Portland Intl.

$238 Roundtrip, found 2 days ago

$238

Roundtrip

found 2 days ago

Select American Airlines flight, departing Thu, Jul 10 from O'Hare Intl. to Portland Intl., returning Wed, Jul 16, priced at $238 found 2 days ago

Tue, Jul 1 - Fri, Jul 11

ORD

O'Hare Intl.

PDX

Portland Intl.

$308 Roundtrip, found 1 day ago

$308

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to Portland Intl., returning Fri, Jul 11, priced at $308 found 1 day ago

Sun, Jul 6 - Tue, Jul 15

MDW

Midway Intl.

PDX

Portland Intl.

$488 Roundtrip, found 14 hours ago

$488

Roundtrip

found 14 hours ago

Select Delta flight, departing Sun, Jul 6 from Midway Intl. to Portland Intl., returning Tue, Jul 15, priced at $488 found 14 hours ago