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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 July , August 2026

30 Jul - 07 Aug $ 350.00
CHI
Chicago
Frontier Airlines
1 STOPS
PDX
Portland
PDX
Portland
Frontier Airlines
1 STOPS
CHI
Chicago
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29 Jul - 17 Aug $ 380.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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29 Jul - 08 Aug $ 409.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Portland

28 Jul - 31 Jul $ 382.00
CHI
Chicago
Frontier Airlines
1 STOPS
PDX
Portland
PDX
Portland
Frontier Airlines
1 STOPS
CHI
Chicago
Pick dates
29 Jul - 31 Jul $ 418.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
Pick dates
31 Jul - 31 Jul $ 420.00
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
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One-way flights to Portland from Chicago

7:20 AM - 7:20 AM
Alaska Airlines
0 Stops
4h 25m
CHI - PDX
$ 202
Kiwi
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7:20 AM - 7:20 AM
Alaska Airlines
0 Stops
4h 25m
CHI - PDX
$ 205
Kiwi
Pick dates
7:20 AM - 7:20 AM
Hawaiian Airlines
0 Stops
4h 25m
CHI - PDX
$ 217
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.