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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 May , June 2026

29 May - 30 Jun $ 305.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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27 May - 09 Jun $ 331.00
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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28 May - 10 Jun $ 341.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Portland

24 May - 31 May $ 385.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
24 May - 01 Jun $ 385.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
1 STOPS
CHI
Chicago
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28 May - 31 May $ 571.00
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

1:29 PM - 1:29 PM
United Airlines
0 Stops
4h 27m
CHI - PDX
$ 153
Kiwi
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1:29 PM - 1:29 PM
United Airlines
0 Stops
4h 27m
CHI - PDX
$ 153
Kiwi
Pick dates
1:29 PM - 1:29 PM
United Airlines
0 Stops
4h 25m
CHI - PDX
$ 384
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.