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

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0 Children (2~11)
0 Infants (0~2)
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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 April , May 2026

29 Apr - 12 May $ 261.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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15 Apr - 09 May $ 459.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates
17 Apr - 09 May $ 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

27 Apr - 30 Apr $ 367.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates
17 Apr - 30 Apr $ 517.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
16 Apr - 30 Apr $ 572.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates

One-way flights to Portland from Chicago

4:05 PM - 4:05 PM
United Airlines
0 Stops
4h 29m
CHI - PDX
$ 136
Kiwi
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2:09 PM - 2:09 PM
Alaska Airlines
0 Stops
4h 41m
CHI - PDX
$ 324
Kiwi
Pick dates
9:30 PM - 9:30 PM
United Airlines
0 Stops
4h 29m
CHI - PDX
$ 334
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.