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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 January , February 2026

30 Jan - 10 Feb $ 294.00
CHI
Chicago
Hawaiian Airlines
DIRECT
PDX
Portland
PDX
Portland
Hawaiian Airlines
DIRECT
CHI
Chicago
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22 Jan - 10 Feb $ 391.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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22 Jan - 03 Feb $ 391.00
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

27 Jan - 31 Jan $ 395.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
18 Jan - 31 Jan $ 485.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
1 STOPS
CHI
Chicago
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19 Jan - 31 Jan $ 565.00
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

2:06 PM - 2:06 PM
Hawaiian Airlines
0 Stops
4h 42m
CHI - PDX
$ 197
Kiwi
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2:06 PM - 2:06 PM
Alaska Airlines
0 Stops
4h 42m
CHI - PDX
$ 282
Kiwi
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4:15 PM - 4:15 PM
United Airlines
0 Stops
4h 41m
CHI - PDX
$ 327
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.