Cheap flights from Portland to Central United States

View AU$144 flight on Mon, 8 Sep. 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

  • Hawaiian Airlines

    Hawaiian Airlines

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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.

Alaska Airlines
Mon, 8 Sep. - Wed, 17 Sep.
PDX
Portland
MSY
New Orleans
AU$286 Return, found 1 day ago
AU$286
Return
found 1 day ago
Select Alaska Airlines flight, departing Mon, 8 Sep. from Portland to New Orleans, returning Wed, 17 Sep., priced at AU$286 found 1 day ago
American Airlines
Thu, 28 Aug. - Wed, 3 Sep.
PDX
Portland
MSY
New Orleans
AU$290 Return, found 5 days ago
AU$290
Return
found 5 days ago
Select American Airlines flight, departing Thu, 28 Aug. from Portland to New Orleans, returning Wed, 3 Sep., priced at AU$290 found 5 days ago
Delta
Mon, 8 Sep. - Wed, 17 Sep.
PDX
Portland
MSY
New Orleans
AU$293 Return, found 1 day ago
AU$293
Return
found 1 day ago
Select Delta flight, departing Mon, 8 Sep. from Portland to New Orleans, returning Wed, 17 Sep., priced at AU$293 found 1 day ago
Delta
Mon, 8 Sep. - Wed, 17 Sep.
PDX
Portland
MSY
New Orleans
AU$299 Return, found 1 day ago
AU$299
Return
found 1 day ago
Select Delta flight, departing Mon, 8 Sep. from Portland to New Orleans, returning Wed, 17 Sep., priced at AU$299 found 1 day ago
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
United
Thu, 4 Sep. - Sun, 7 Sep.
PDX
Portland
AUS
Austin
AU$478 Return, found 6 days ago
AU$478
Return
found 6 days ago
Select United flight, departing Thu, 4 Sep. from Portland to Austin, returning Sun, 7 Sep., priced at AU$478 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.