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

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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 March , April 2026

31 Mar - 21 Apr $ 272.00
PDX
Portland
Hawaiian Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
PDX
Portland
Pick dates
14 Mar - 08 Apr $ 327.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates
14 Mar - 07 Apr $ 327.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates

Last minute flights from Portland to Chicago

30 Mar - 31 Mar $ 399.00
PDX
Portland
Hawaiian Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
PDX
Portland
Pick dates
14 Mar - 31 Mar $ 412.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates
15 Mar - 31 Mar $ 505.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates

One-way flights to Chicago from Portland

11:59 PM - 11:59 PM
United Airlines
0 Stops
3h 54m
PDX - CHI
$ 144
Kiwi
Pick dates
7:00 AM - 7:00 AM
Alaska Airlines
0 Stops
4h 11m
PDX - CHI
$ 197
Kiwi
Pick dates
11:28 PM - 11:28 PM
United Airlines
0 Stops
3h 52m
PDX - CHI
$ 354
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.