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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 March , April 2025

31 Mar - 12 Apr $ 354.00
PDX
Portland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PDX
Portland
Pick dates
09 Mar - 19 Apr $ 626.00
PDX
Portland
United Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
PDX
Portland
Pick dates
09 Mar - 19 Apr $ 626.00
PDX
Portland
United Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
PDX
Portland
Pick dates

Last minute flights from Portland to Chicago

28 Mar - 31 Mar $ 569.00
PDX
Portland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PDX
Portland
Pick dates
25 Mar - 31 Mar $ 569.00
PDX
Portland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PDX
Portland
Pick dates
26 Mar - 31 Mar $ 577.00
PDX
Portland
Hawaiian Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
PDX
Portland
Pick dates

One-way flights to Chicago from Portland

11:59 PM - 11:59 PM
United Airlines
0 Stops
3h 57m
PDX - CHI
$ 178
Kiwi
Pick dates
11:00 AM - 11:00 AM
United Airlines
0 Stops
3h 57m
PDX - CHI
$ 342
Kiwi
Pick dates
11:58 PM - 11:58 PM
United Airlines
0 Stops
3h 57m
PDX - CHI
$ 349
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.