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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

30 Apr - 28 May $ 456.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
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30 Apr - 09 May $ 546.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
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24 Apr - 14 May $ 635.00
PDX
Portland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PDX
Portland
Pick dates

Last minute flights from Portland to Chicago

30 Apr - 30 Apr $ 657.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
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27 Apr - 30 Apr $ 707.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates
27 Apr - 30 Apr $ 772.00
PDX
Portland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PDX
Portland
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One-way flights to Chicago from Portland

7:55 AM - 7:55 AM
Alaska Airlines
0 Stops
4h 13m
PDX - CHI
$ 324
Kiwi
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8:45 AM - 10:32 AM
Alaska Airlines
1 Stops
6h 11m
PDX - CHI
$ 334
Kiwi
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2:41 PM - 2:41 PM
United Airlines
0 Stops
4h 2m
PDX - CHI
$ 344
Kiwi
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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.