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

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
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How to find the cheapest flight from Portland (PDX) to Chicago (CHI)

How to find the cheapest flight from Portland (PDX) to Chicago (CHI)
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How to find the cheapest flight from Portland (PDX) to Chicago (CHI)
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How to find the cheapest flight from Portland (PDX) to Chicago (CHI)
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Cheap flights from Portland to Chicago in April , May 2026

29 Apr - 16 May $ 263.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
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09 Apr - 05 May $ 459.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
Pick dates
09 Apr - 05 May $ 461.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates

Last minute flights from Portland to Chicago

28 Apr - 30 Apr $ 286.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
Pick dates
09 Apr - 30 Apr $ 474.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
Pick dates
09 Apr - 30 Apr $ 607.00
PDX
Portland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PDX
Portland
Pick dates

One-way flights to Chicago from Portland

11:59 PM - 11:59 PM
United Airlines
0 Stops
4h 4m
PDX - CHI
$ 126
Kiwi
Pick dates
11:59 PM - 11:59 PM
United Airlines
0 Stops
4h 4m
PDX - CHI
$ 324
Kiwi
Pick dates
2:30 PM - 2:30 PM
United Airlines
0 Stops
4h 4m
PDX - CHI
$ 324
Kiwi
Pick dates

How to find the cheapest flight from Portland (PDX) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Portland (PDX) to Chicago (CHI)
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 Portland (PDX) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.