Chicago to Portland Flights from US$166 incl. tax

Discover the best flight deals from Chicago to Portland

Chicago to Portland Flights

Compare and book the best deals

09:29
MDW
Chicago
5h 31m
1 stop
16:00
PWM
Portland
US$488
US$166
66% OFF
08:36
ORD
Chicago
13h 36m
1 stop
23:12
PWM
Portland
US$488
US$196
60% OFF
06:00
ORD
Chicago
16h 22m
1 stop
23:22
PWM
Portland
US$488
US$203
57% OFF
06:00
ORD
Chicago
16h 22m
1 stop
23:22
PWM
Portland
US$488
US$203
57% OFF
18:25
ORD
Chicago
4h 55m
1 stop
00:20
PWM
Portland
US$367
US$217
41% OFF
07:00
ORD
Chicago
5h 54m
1 stop
13:54
PWM
Portland
US$488
US$228
53% OFF

Chicago to Portland Arrival Airports

Airports in Portland

Chicago to Portland Airlines

Airlines operating flights on this route