Cheap flights from Chicago to Willamette Valley

View AU$152 flight on Tue, 30 Sep. 2025Opens in a new window

Popular airlines from Chicago to Willamette Valley

  • Jetstar

    Jetstar

  • Qantas Airways

    Qantas Airways

  • Virgin Australia

    Virgin Australia

  • Scoot

    Scoot

  • American Airlines

    American Airlines

  • Emirates

    Emirates

  • United

    United

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Cheap Flights from Chicago (CHI) to Willamette Valley (RDM)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Sat, 16 Aug. - Sat, 23 Aug.
ORD
Chicago
PDX
Portland
AU$351 Return, found 18 hours ago
AU$351
Return
found 18 hours ago
Select Alaska Airlines flight, departing Sat, 16 Aug. from Chicago to Portland, returning Sat, 23 Aug., priced at AU$351 found 18 hours ago
American Airlines
Sat, 16 Aug. - Sat, 23 Aug.
ORD
Chicago
PDX
Portland
AU$352 Return, found 18 hours ago
AU$352
Return
found 18 hours ago
Select American Airlines flight, departing Sat, 16 Aug. from Chicago to Portland, returning Sat, 23 Aug., priced at AU$352 found 18 hours ago
Alaska Airlines
Sat, 16 Aug. - Sat, 23 Aug.
ORD
Chicago
PDX
Portland
AU$367 Return, found 18 hours ago
AU$367
Return
found 18 hours ago
Select Alaska Airlines flight, departing Sat, 16 Aug. from Chicago to Portland, returning Sat, 23 Aug., priced at AU$367 found 18 hours ago
American Airlines
Sat, 16 Aug. - Sat, 23 Aug.
ORD
Chicago
PDX
Portland
AU$396 Return, found 18 hours ago
AU$396
Return
found 18 hours ago
Select American Airlines flight, departing Sat, 16 Aug. from Chicago to Portland, returning Sat, 23 Aug., priced at AU$396 found 18 hours ago
United
Sat, 16 Aug. - Sat, 23 Aug.
ORD
Chicago
PDX
Portland
AU$451 Return, found 18 hours ago
AU$451
Return
found 18 hours ago
Select United flight, departing Sat, 16 Aug. from Chicago to Portland, returning Sat, 23 Aug., priced at AU$451 found 18 hours ago
Delta
Sat, 16 Aug. - Sat, 23 Aug.
ORD
Chicago
PDX
Portland
AU$464 Return, found 18 hours ago
AU$464
Return
found 18 hours ago
Select Delta flight, departing Sat, 16 Aug. from Chicago to Portland, returning Sat, 23 Aug., priced at AU$464 found 18 hours ago

Find the cheapest month to fly from Chicago (CHI) to Portland (PDX)

August is typically the cheapest month to fly

From AU$151 - AU$338 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.