Flights from Chicago to Brightwood

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, Oct 16 - Fri, Oct 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$189 Roundtrip, found 22 hours ago

$189

Roundtrip

found 22 hours ago

Select Frontier Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Portland Intl., returning Fri, Oct 17, priced at $189 found 22 hours ago

Thu, Oct 16 - Fri, Oct 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$206 Roundtrip, found 22 hours ago

$206

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Portland Intl., returning Fri, Oct 17, priced at $206 found 22 hours ago

Mon, Oct 13 - Sat, Oct 18

ORD

O'Hare Intl.

PDX

Portland Intl.

$216 Roundtrip, found 22 hours ago

$216

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Mon, Oct 13 from O'Hare Intl. to Portland Intl., returning Sat, Oct 18, priced at $216 found 22 hours ago

Sat, Oct 18 - Wed, Oct 22

ORD

O'Hare Intl.

PDX

Portland Intl.

$227 Roundtrip, found 22 hours ago

$227

Roundtrip

found 22 hours ago

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

Tue, Oct 14 - Sat, Oct 18

ORD

O'Hare Intl.

PDX

Portland Intl.

$230 Roundtrip, found 22 hours ago

$230

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Tue, Oct 14 from O'Hare Intl. to Portland Intl., returning Sat, Oct 18, priced at $230 found 22 hours ago

Thu, Oct 16 - Fri, Oct 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$232 Roundtrip, found 22 hours ago

$232

Roundtrip

found 22 hours ago

Select Alaska Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Portland Intl., returning Fri, Oct 17, priced at $232 found 22 hours ago

Sat, Sep 6 - Sat, Sep 20

ORD

O'Hare Intl.

PDX

Portland Intl.

$232 Roundtrip, found 1 day ago

$232

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Sat, Sep 6 from O'Hare Intl. to Portland Intl., returning Sat, Sep 20, priced at $232 found 1 day ago

Thu, Oct 16 - Fri, Oct 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$236 Roundtrip, found 22 hours ago

$236

Roundtrip

found 22 hours ago

Select Frontier Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Portland Intl., returning Fri, Oct 17, priced at $236 found 22 hours ago

Wed, Oct 15 - Wed, Oct 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$237 Roundtrip, found 22 hours ago

$237

Roundtrip

found 22 hours ago

Select Alaska Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Portland Intl., returning Wed, Oct 15, priced at $237 found 22 hours ago

Thu, Oct 16 - Fri, Oct 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$238 Roundtrip, found 22 hours ago

$238

Roundtrip

found 22 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Portland Intl., returning Fri, Oct 17, priced at $238 found 22 hours ago

Fri, Oct 17 - Wed, Oct 22

ORD

O'Hare Intl.

PDX

Portland Intl.

$238 Roundtrip, found 22 hours ago

$238

Roundtrip

found 22 hours ago

Select Hawaiian Airlines flight, departing Fri, Oct 17 from O'Hare Intl. to Portland Intl., returning Wed, Oct 22, priced at $238 found 22 hours ago

Mon, Oct 13 - Tue, Oct 14

ORD

O'Hare Intl.

PDX

Portland Intl.

$240 Roundtrip, found 22 hours ago

$240

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Mon, Oct 13 from O'Hare Intl. to Portland Intl., returning Tue, Oct 14, priced at $240 found 22 hours ago

Sat, Oct 18 - Sat, Oct 18

ORD

O'Hare Intl.

PDX

Portland Intl.

$242 Roundtrip, found 22 hours ago

$242

Roundtrip

found 22 hours ago

Select Alaska Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Portland Intl., returning Sat, Oct 18, priced at $242 found 22 hours ago

Sat, Oct 18 - Sun, Oct 19

ORD

O'Hare Intl.

PDX

Portland Intl.

$242 Roundtrip, found 22 hours ago

$242

Roundtrip

found 22 hours ago

Select Hawaiian Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Portland Intl., returning Sun, Oct 19, priced at $242 found 22 hours ago

Sat, Sep 6 - Sun, Sep 14

ORD

O'Hare Intl.

PDX

Portland Intl.

$243 Roundtrip, found 1 day ago

$243

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Sat, Sep 6 from O'Hare Intl. to Portland Intl., returning Sun, Sep 14, priced at $243 found 1 day ago

Wed, Oct 15 - Tue, Oct 21

ORD

O'Hare Intl.

PDX

Portland Intl.

$246 Roundtrip, found 22 hours ago

$246

Roundtrip

found 22 hours ago

Select Alaska Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Portland Intl., returning Tue, Oct 21, priced at $246 found 22 hours ago

Tue, Oct 14 - Wed, Oct 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$247 Roundtrip, found 22 hours ago

$247

Roundtrip

found 22 hours ago

Select Delta flight, departing Tue, Oct 14 from O'Hare Intl. to Portland Intl., returning Wed, Oct 15, priced at $247 found 22 hours ago

Sat, Sep 6 - Thu, Sep 18

ORD

O'Hare Intl.

PDX

Portland Intl.

$247 Roundtrip, found 1 day ago

$247

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Sat, Sep 6 from O'Hare Intl. to Portland Intl., returning Thu, Sep 18, priced at $247 found 1 day ago

Thu, Oct 16 - Fri, Oct 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$249 Roundtrip, found 22 hours ago

$249

Roundtrip

found 22 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Portland Intl., returning Fri, Oct 17, priced at $249 found 22 hours ago

Thu, Oct 16 - Fri, Oct 17

ORD

O'Hare Intl.

PDX

Portland Intl.

$249 Roundtrip, found 22 hours ago

$249

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Portland Intl., returning Fri, Oct 17, priced at $249 found 22 hours ago