Earn point on your loyalty program!arrow arc left

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

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Portland (PDX) to Chicago (CHI)

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.
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.

Cheap flights from Portland to Chicago in August , September 2026

25 Aug - 10 Sep $ 307.00
PDX
Portland
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
PDX
Portland
Pick dates
29 Aug - 16 Sep $ 397.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates
17 Aug - 10 Sep $ 430.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates

Last minute flights from Portland to Chicago

25 Aug - 01 Sep $ 389.00
PDX
Portland
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
PDX
Portland
Pick dates
29 Aug - 31 Aug $ 460.00
PDX
Portland
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
DIRECT
PDX
Portland
Pick dates
24 Aug - 31 Aug $ 583.00
PDX
Portland
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PDX
Portland
Pick dates

One-way flights to Chicago from Portland

11:02 PM - 11:02 PM
United Airlines
0 Stops
4h 1m
PDX - CHI
$ 219
Kiwi
Pick dates
11:02 PM - 11:02 PM
United Airlines
0 Stops
4h 1m
PDX - CHI
$ 229
Kiwi
Pick dates
11:02 PM - 11:02 PM
United Airlines
0 Stops
4h 1m
PDX - CHI
$ 229
Kiwi
Pick dates

How to find the cheapest flight from Portland (PDX) to Chicago (CHI)

Related info for your journey
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.
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.