Cheap flights from Chicago to Willamette Valley

View AU$151 flight on Sat, 23 Aug. 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.

American Airlines
Sat, 23 Aug. - Sat, 30 Aug.
ORD
Chicago
PDX
Portland
AU$288 Return, found 6 days ago
AU$288
Return
found 6 days ago
Select American Airlines flight, departing Sat, 23 Aug. from Chicago to Portland, returning Sat, 30 Aug., priced at AU$288 found 6 days ago
Alaska Airlines
Sat, 23 Aug. - Sat, 30 Aug.
ORD
Chicago
PDX
Portland
AU$302 Return, found 6 days ago
AU$302
Return
found 6 days ago
Select Alaska Airlines flight, departing Sat, 23 Aug. from Chicago to Portland, returning Sat, 30 Aug., priced at AU$302 found 6 days ago
Alaska Airlines
Sat, 23 Aug. - Sat, 30 Aug.
ORD
Chicago
PDX
Portland
AU$303 Return, found 6 days ago
AU$303
Return
found 6 days ago
Select Alaska Airlines flight, departing Sat, 23 Aug. from Chicago to Portland, returning Sat, 30 Aug., priced at AU$303 found 6 days ago
American Airlines
Fri, 22 Aug. - Sat, 30 Aug.
ORD
Chicago
PDX
Portland
AU$304 Return, found 6 days ago
AU$304
Return
found 6 days ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to Portland, returning Sat, 30 Aug., priced at AU$304 found 6 days ago
Delta
Sat, 23 Aug. - Sat, 30 Aug.
ORD
Chicago
PDX
Portland
AU$317 Return, found 6 days ago
AU$317
Return
found 6 days ago
Select Delta flight, departing Sat, 23 Aug. from Chicago to Portland, returning Sat, 30 Aug., priced at AU$317 found 6 days ago
United
Sat, 23 Aug. - Sat, 30 Aug.
ORD
Chicago
PDX
Portland
AU$373 Return, found 6 days ago
AU$373
Return
found 6 days ago
Select United flight, departing Sat, 23 Aug. from Chicago to Portland, returning Sat, 30 Aug., priced at AU$373 found 6 days 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.