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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 May , June 2026

27 May - 24 Jun $ 308.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
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27 May - 10 Jun $ 319.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
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18 May - 15 Jun $ 719.00
PDX
Portland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PDX
Portland
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Last minute flights from Portland to Chicago

27 May - 31 May $ 420.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates
24 May - 31 May $ 475.00
PDX
Portland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PDX
Portland
Pick dates
24 May - 31 May $ 475.00
PDX
Portland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
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One-way flights to Chicago from Portland

7:00 AM - 7:00 AM
Alaska Airlines
0 Stops
4h 22m
PDX - CHI
$ 152
Kiwi
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10:40 PM - 10:40 PM
United Airlines
0 Stops
4h 5m
PDX - CHI
$ 153
Kiwi
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2:41 PM - 2:41 PM
United Airlines
0 Stops
3h 59m
PDX - CHI
$ 384
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.