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Cheap flights from Chicago (CHI) to Portland (PDX)

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0 Children (2~11)
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How to find the cheapest flight from Chicago (CHI) to Portland (PDX)

How to find the cheapest flight from Chicago (CHI) to Portland (PDX)
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How to find the cheapest flight from Chicago (CHI) to Portland (PDX)
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How to find the cheapest flight from Chicago (CHI) to Portland (PDX)
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Cheap flights from Chicago to Portland in November , December 2025

27 Nov - 09 Dec $ 255.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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28 Nov - 06 Dec $ 386.00
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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28 Nov - 01 Dec $ 681.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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Last minute flights from Chicago to Portland

28 Nov - 01 Dec $ 583.00
CHI
Chicago
Sun Country Airlines
1 STOPS
PDX
Portland
PDX
Portland
Sun Country Airlines
1 STOPS
CHI
Chicago
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28 Nov - 30 Nov $ 681.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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25 Nov - 30 Nov $ 1,005.00
CHI
Chicago
United Airlines
DIRECT
PDX
Portland
PDX
Portland
United Airlines
DIRECT
CHI
Chicago
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One-way flights to Portland from Chicago

7:00 AM - 7:00 AM
Alaska Airlines
0 Stops
4h 39m
CHI - PDX
$ 301
Kiwi
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2:10 PM - 2:10 PM
Alaska Airlines
0 Stops
4h 40m
CHI - PDX
$ 301
Kiwi
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4:05 PM - 4:05 PM
United Airlines
0 Stops
4h 35m
CHI - PDX
$ 349
Kiwi
Pick dates

How to find the cheapest flight from Chicago (CHI) to Portland (PDX)

Related info for your journey
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How to find the cheapest flight from Chicago (CHI) to Portland (PDX)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Chicago (CHI) to Portland (PDX)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.