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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 September , October 2026

28 Sep - 11 Oct $ 398.00
PDX
Portland
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
PDX
Portland
Pick dates
29 Sep - 22 Oct $ 423.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates
30 Sep - 01 Oct $ 515.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates

Last minute flights from Portland to Chicago

28 Sep - 01 Oct $ 398.00
PDX
Portland
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
PDX
Portland
Pick dates
29 Sep - 30 Sep $ 492.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates
28 Sep - 30 Sep $ 640.00
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

12:39 PM - 11:50 PM
Frontier Airlines
1 Stops
14h 59m
PDX - CHI
$ 202
Kiwi
Pick dates
11:30 PM - 11:30 PM
United Airlines
0 Stops
4h 1m
PDX - CHI
$ 249
Kiwi
Pick dates
11:30 PM - 11:30 PM
United Airlines
0 Stops
4h 1m
PDX - CHI
$ 249
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.