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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 November , December 2025

27 Nov - 25 Dec $ 309.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
PDX
Portland
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28 Nov - 10 Dec $ 450.00
PDX
Portland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
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22 Nov - 20 Dec $ 827.00
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

23 Nov - 30 Nov $ 474.00
PDX
Portland
Sun Country Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Sun Country Airlines
1 STOPS
PDX
Portland
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28 Nov - 01 Dec $ 726.00
PDX
Portland
Sun Country Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Sun Country Airlines
1 STOPS
PDX
Portland
Pick dates
24 Nov - 30 Nov $ 1,382.00
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

7:07 AM - 7:07 AM
Alaska Airlines
0 Stops
4h 7m
PDX - CHI
$ 300
Kiwi
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6:36 PM - 7:12 AM
Sun Country Airlines
1 Stops
12h 26m
PDX - CHI
$ 304
Kiwi
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11:59 PM - 11:59 PM
United Airlines
0 Stops
3h 53m
PDX - CHI
$ 374
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.