Cheap flights from Portland to South Suburbs

View AU$139 flight on Sun, 31 Aug. 2025Opens in a new window

Popular airlines from Portland to South Suburbs

  • 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 Portland (PDX) to South Suburbs (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
Fri, 26 Sep. - Sat, 27 Sep.
PDX
Portland
ORD
Chicago
AU$311 Return, found 5 days ago
AU$311
Return
found 5 days ago
Select Hawaiian Airlines flight, departing Fri, 26 Sep. from Portland to Chicago, returning Sat, 27 Sep., priced at AU$311 found 5 days ago
Hawaiian Airlines
Sun, 21 Sep. - Sat, 27 Sep.
PDX
Portland
ORD
Chicago
AU$320 Return, found 5 days ago
AU$320
Return
found 5 days ago
Select Hawaiian Airlines flight, departing Sun, 21 Sep. from Portland to Chicago, returning Sat, 27 Sep., priced at AU$320 found 5 days ago
Alaska Airlines
Thu, 21 Aug. - Thu, 28 Aug.
PDX
Portland
ORD
Chicago
AU$335 Return, found 2 days ago
AU$335
Return
found 2 days ago
Select Alaska Airlines flight, departing Thu, 21 Aug. from Portland to Chicago, returning Thu, 28 Aug., priced at AU$335 found 2 days ago
American Airlines
Thu, 21 Aug. - Thu, 28 Aug.
PDX
Portland
ORD
Chicago
AU$336 Return, found 2 days ago
AU$336
Return
found 2 days ago
Select American Airlines flight, departing Thu, 21 Aug. from Portland to Chicago, returning Thu, 28 Aug., priced at AU$336 found 2 days ago
Delta
Wed, 24 Sep. - Tue, 30 Sep.
PDX
Portland
ORD
Chicago
AU$342 Return, found 2 days ago
AU$342
Return
found 2 days ago
Select Delta flight, departing Wed, 24 Sep. from Portland to Chicago, returning Tue, 30 Sep., priced at AU$342 found 2 days ago
United
Wed, 24 Sep. - Tue, 30 Sep.
PDX
Portland
ORD
Chicago
AU$396 Return, found 2 days ago
AU$396
Return
found 2 days ago
Select United flight, departing Wed, 24 Sep. from Portland to Chicago, returning Tue, 30 Sep., priced at AU$396 found 2 days 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.