Portland to Chicago Flights from US$110 incl. tax

Discover the best flight deals from Portland to Chicago

Portland to Chicago Flights

Compare and book the best deals

17:56
PWM
Portland
5h 38m
1 stop
22:34
ORD
Chicago
US$205
US$110
46% OFF
12:48
PWM
Portland
4h 52m
1 stop
16:40
ORD
Chicago
US$205
US$110
46% OFF
05:30
PWM
Portland
6h 4m
1 stop
10:34
MDW
Chicago
US$205
US$110
46% OFF
06:08
PWM
Portland
6h 47m
1 stop
11:55
MDW
Chicago
US$205
US$110
46% OFF
12:48
PWM
Portland
4h 50m
1 stop
16:38
ORD
Chicago
US$205
US$110
46% OFF
12:20
PWM
Portland
6h 14m
1 stop
17:34
MDW
Chicago
US$205
US$110
47% OFF

Portland to Chicago Departure Airports

Airports in Portland

Portland to Chicago Airlines

Airlines operating flights on this route