Cheap flights from Portland to Central United States

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

Popular airlines from Portland to Central United States

  • American Airlines

    American Airlines

  • Alaska Airlines

    Alaska Airlines

  • Delta

    Delta

  • United

    United

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Cheap Flights from Portland (PDX) to Central United States (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.

American Airlines
Thu, 28 Aug. - Wed, 3 Sep.
PDX
Portland
MSY
New Orleans
AU$290 Return, found 1 day ago
AU$290
Return
found 1 day ago
Select American Airlines flight, departing Thu, 28 Aug. from Portland to New Orleans, returning Wed, 3 Sep., priced at AU$290 found 1 day ago
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
Delta
Thu, 14 Aug. - Wed, 24 Sep.
PDX
Portland
MSP
Minneapolis
AU$318 Return, found 6 days ago
AU$318
Return
found 6 days ago
Select Delta flight, departing Thu, 14 Aug. from Portland to Minneapolis, returning Wed, 24 Sep., priced at AU$318 found 6 days ago
Alaska Airlines
Tue, 14 Oct. - Mon, 20 Oct.
PDX
Portland
MSP
Minneapolis
AU$320 Return, found 4 days ago
AU$320
Return
found 4 days ago
Select Alaska Airlines flight, departing Tue, 14 Oct. from Portland to Minneapolis, returning Mon, 20 Oct., priced at AU$320 found 4 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
United
Thu, 14 Aug. - Wed, 24 Sep.
PDX
Portland
MSP
Minneapolis
AU$449 Return, found 6 days ago
AU$449
Return
found 6 days ago
Select United flight, departing Thu, 14 Aug. from Portland to Minneapolis, returning Wed, 24 Sep., priced at AU$449 found 6 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.