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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 October , November 2026

22 Oct - 18 Nov $ 334.00
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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22 Oct - 10 Nov $ 339.00
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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27 Oct - 10 Nov $ 399.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Portland

22 Oct - 31 Oct $ 456.00
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates
27 Oct - 31 Oct $ 463.00
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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24 Oct - 31 Oct $ 661.00
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

6:30 AM - 9:00 AM
Frontier Airlines
1 Stops
6h 24m
CHI - PDX
$ 184
Kiwi
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6:30 AM - 9:00 AM
Frontier Airlines
1 Stops
6h 24m
CHI - PDX
$ 184
Kiwi
Pick dates
1:30 PM - 1:30 PM
United Airlines
0 Stops
4h 26m
CHI - PDX
$ 265
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.