Cheap flights from Portland to Rush Street

View AU$176 flight on Sat, 23 Aug. 2025Opens in a new window

Popular airlines from Portland to Rush Street

  • Delta

    Delta

  • American Airlines

    American Airlines

  • Alaska Airlines

    Alaska Airlines

  • United

    United

  • Hawaiian Airlines

    Hawaiian Airlines

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Cheap Flights from Portland (PDX) to Rush Street (CHI)

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.

Hawaiian Airlines
Sat, 27 Sep. - Tue, 30 Sep.
PDX
Portland
ORD
Chicago
AU$344 Return, found 1 day ago
AU$344
Return
found 1 day ago
Select Hawaiian Airlines flight, departing Sat, 27 Sep. from Portland to Chicago, returning Tue, 30 Sep., priced at AU$344 found 1 day ago
American Airlines
Wed, 24 Sep. - Tue, 30 Sep.
PDX
Portland
ORD
Chicago
AU$345 Return, found 1 day ago
AU$345
Return
found 1 day ago
Select American Airlines flight, departing Wed, 24 Sep. from Portland to Chicago, returning Tue, 30 Sep., priced at AU$345 found 1 day ago
Alaska Airlines
Sun, 24 Aug. - Sat, 30 Aug.
PDX
Portland
ORD
Chicago
AU$347 Return, found 19 hours ago
AU$347
Return
found 19 hours ago
Select Alaska Airlines flight, departing Sun, 24 Aug. from Portland to Chicago, returning Sat, 30 Aug., priced at AU$347 found 19 hours ago
Hawaiian Airlines
Fri, 26 Sep. - Sat, 27 Sep.
PDX
Portland
ORD
Chicago
AU$352 Return, found 1 day ago
AU$352
Return
found 1 day ago
Select Hawaiian Airlines flight, departing Fri, 26 Sep. from Portland to Chicago, returning Sat, 27 Sep., priced at AU$352 found 1 day ago
Delta
Wed, 24 Sep. - Tue, 30 Sep.
PDX
Portland
ORD
Chicago
AU$360 Return, found 1 day ago
AU$360
Return
found 1 day ago
Select Delta flight, departing Wed, 24 Sep. from Portland to Chicago, returning Tue, 30 Sep., priced at AU$360 found 1 day ago
United
Wed, 24 Sep. - Tue, 30 Sep.
PDX
Portland
ORD
Chicago
AU$481 Return, found 1 day ago
AU$481
Return
found 1 day ago
Select United flight, departing Wed, 24 Sep. from Portland to Chicago, returning Tue, 30 Sep., priced at AU$481 found 1 day ago

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

August is typically the cheapest month to fly

From AU$135 - AU$295 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.