$153 Cheap Alaska Airlines flights Portland (PDX) to Chicago (ORD)

View $153 flight on Fri, May 29, 2026Opens in a new window

$153 Cheap Alaska Airlines flights Portland (PDX) to Chicago (ORD)

Prices were available within the past 7 days and start at $153 for one-way flights and $351 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Wed, May 27 - Fri, Jun 5
PDX
Portland
ORD
Chicago
$351 Roundtrip, found 1 day ago
$351
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, May 27 from Portland to Chicago, returning Fri, Jun 5, priced at $351 found 1 day ago
Alaska Airlines
Fri, May 29 - Tue, Jun 2
PDX
Portland
ORD
Chicago
$420 Roundtrip, found 1 day ago
$420
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Fri, May 29 from Portland to Chicago, returning Tue, Jun 2, priced at $420 found 1 day ago
Alaska Airlines
Sat, May 30 - Tue, Jun 2
PDX
Portland
ORD
Chicago
$445 Roundtrip, found 1 day ago
$445
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, May 30 from Portland to Chicago, returning Tue, Jun 2, priced at $445 found 1 day ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $431
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $431

Travel information

Origin airport
Portland Intl.
Destination airport
O'Hare Intl.
Distance
2774 km
Average flight time
6 hours 5 mins

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