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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 March , April 2026

24 Mar - 18 Apr $ 341.00
CHI
Chicago
Hawaiian Airlines
DIRECT
PDX
Portland
PDX
Portland
Hawaiian Airlines
DIRECT
CHI
Chicago
Pick dates
14 Mar - 01 Apr $ 436.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates
15 Mar - 01 Apr $ 459.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Portland

23 Mar - 31 Mar $ 352.00
CHI
Chicago
Hawaiian Airlines
DIRECT
PDX
Portland
PDX
Portland
Hawaiian Airlines
DIRECT
CHI
Chicago
Pick dates
14 Mar - 31 Mar $ 436.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates
15 Mar - 31 Mar $ 459.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates

One-way flights to Portland from Chicago

4:40 PM - 4:40 PM
United Airlines
0 Stops
4h 34m
CHI - PDX
$ 203
Kiwi
Pick dates
4:40 PM - 4:40 PM
United Airlines
0 Stops
4h 34m
CHI - PDX
$ 294
Kiwi
Pick dates
8:04 PM - 8:04 PM
United Airlines
0 Stops
4h 41m
CHI - PDX
$ 294
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.