Flights from Chicago to The Dalles

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.

Sun, Aug 31 - Sun, Aug 31

ORD

O'Hare Intl.

PDX

Portland Intl.

$179 Roundtrip, found 5 days ago

$179

Roundtrip

found 5 days ago

Select Hawaiian Airlines flight, departing Sun, Aug 31 from O'Hare Intl. to Portland Intl., returning Sun, Aug 31, priced at $179 found 5 days ago

Sat, Aug 30 - Sun, Aug 31

ORD

O'Hare Intl.

PDX

Portland Intl.

$180 Roundtrip, found 5 days ago

$180

Roundtrip

found 5 days ago

Select Hawaiian Airlines flight, departing Sat, Aug 30 from O'Hare Intl. to Portland Intl., returning Sun, Aug 31, priced at $180 found 5 days ago

Sat, Aug 30 - Sat, Aug 30

ORD

O'Hare Intl.

PDX

Portland Intl.

$181 Roundtrip, found 5 days ago

$181

Roundtrip

found 5 days ago

Select Hawaiian Airlines flight, departing Sat, Aug 30 from O'Hare Intl. to Portland Intl., returning Sat, Aug 30, priced at $181 found 5 days ago

Sun, Aug 31 - Tue, Sep 2

ORD

O'Hare Intl.

PDX

Portland Intl.

$190 Roundtrip, found 5 days ago

$190

Roundtrip

found 5 days ago

Select Hawaiian Airlines flight, departing Sun, Aug 31 from O'Hare Intl. to Portland Intl., returning Tue, Sep 2, priced at $190 found 5 days ago

Wed, Jul 9 - Thu, Jul 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$190 Roundtrip, found 3 days ago

$190

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Thu, Jul 17, priced at $190 found 3 days ago

Fri, Aug 29 - Sun, Aug 31

ORD

O'Hare Intl.

PDX

Portland Intl.

$193 Roundtrip, found 5 days ago

$193

Roundtrip

found 5 days ago

Select Hawaiian Airlines flight, departing Fri, Aug 29 from O'Hare Intl. to Portland Intl., returning Sun, Aug 31, priced at $193 found 5 days ago

Tue, Aug 5 - Sun, Aug 10

ORD

O'Hare Intl.

PDX

Portland Intl.

$196 Roundtrip, found 5 days ago

$196

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Portland Intl., returning Sun, Aug 10, priced at $196 found 5 days ago

Fri, Aug 29 - Tue, Sep 2

ORD

O'Hare Intl.

PDX

Portland Intl.

$204 Roundtrip, found 5 days ago

$204

Roundtrip

found 5 days ago

Select Hawaiian Airlines flight, departing Fri, Aug 29 from O'Hare Intl. to Portland Intl., returning Tue, Sep 2, priced at $204 found 5 days ago

Fri, Aug 29 - Thu, Sep 4

ORD

O'Hare Intl.

PDX

Portland Intl.

$207 Roundtrip, found 5 days ago

$207

Roundtrip

found 5 days ago

Select Hawaiian Airlines flight, departing Fri, Aug 29 from O'Hare Intl. to Portland Intl., returning Thu, Sep 4, priced at $207 found 5 days ago

Sat, Aug 2 - Thu, Aug 7

ORD

O'Hare Intl.

PDX

Portland Intl.

$216 Roundtrip, found 6 days ago

$216

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Portland Intl., returning Thu, Aug 7, priced at $216 found 6 days ago

Wed, Jul 30 - Fri, Aug 8

ORD

O'Hare Intl.

PDX

Portland Intl.

$217 Roundtrip, found 6 days ago

$217

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Jul 30 from O'Hare Intl. to Portland Intl., returning Fri, Aug 8, priced at $217 found 6 days ago

Wed, Jul 30 - Fri, Aug 8

ORD

O'Hare Intl.

PDX

Portland Intl.

$217 Roundtrip, found 6 days ago

$217

Roundtrip

found 6 days ago

Select United flight, departing Wed, Jul 30 from O'Hare Intl. to Portland Intl., returning Fri, Aug 8, priced at $217 found 6 days ago

Sat, Aug 2 - Tue, Aug 12

ORD

O'Hare Intl.

PDX

Portland Intl.

$222 Roundtrip, found 5 days ago

$222

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Portland Intl., returning Tue, Aug 12, priced at $222 found 5 days ago

Fri, Aug 29 - Tue, Sep 2

ORD

O'Hare Intl.

PDX

Portland Intl.

$225 Roundtrip, found 5 days ago

$225

Roundtrip

found 5 days ago

Select United flight, departing Fri, Aug 29 from O'Hare Intl. to Portland Intl., returning Tue, Sep 2, priced at $225 found 5 days ago

Sat, Oct 18 - Wed, Oct 22

ORD

O'Hare Intl.

PDX

Portland Intl.

$227 Roundtrip, found 4 days ago

$227

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Portland Intl., returning Wed, Oct 22, priced at $227 found 4 days ago

Fri, Aug 29 - Tue, Sep 2

ORD

O'Hare Intl.

PDX

Portland Intl.

$229 Roundtrip, found 5 days ago

$229

Roundtrip

found 5 days ago

Select Alaska Airlines flight, departing Fri, Aug 29 from O'Hare Intl. to Portland Intl., returning Tue, Sep 2, priced at $229 found 5 days ago

Sat, Oct 18 - Fri, Oct 24

ORD

O'Hare Intl.

PDX

Portland Intl.

$231 Roundtrip, found 4 days ago

$231

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Portland Intl., returning Fri, Oct 24, priced at $231 found 4 days ago

Wed, Oct 15 - Tue, Oct 21

ORD

O'Hare Intl.

PDX

Portland Intl.

$233 Roundtrip, found 4 days ago

$233

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Portland Intl., returning Tue, Oct 21, priced at $233 found 4 days ago

Wed, Jul 23 - Wed, Jul 30

ORD

O'Hare Intl.

PDX

Portland Intl.

$237 Roundtrip, found 1 day ago

$237

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 23 from O'Hare Intl. to Portland Intl., returning Wed, Jul 30, priced at $237 found 1 day ago

Wed, Jul 23 - Wed, Jul 30

ORD

O'Hare Intl.

PDX

Portland Intl.

$275 Roundtrip, found 1 day ago

$275

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Jul 23 from O'Hare Intl. to Portland Intl., returning Wed, Jul 30, priced at $275 found 1 day ago