Fly nonstop from Portland to Chicago for $247 round-trip on American.
Searching AA.com, we found seats departing PDX on Mondaoy, September 14, returning from ORD on Sunday, September 20.
Other dates are also available for travel from September 8 through December 15.
See our Fare Details for booking info.
Need a room in Chicago? Here's what's available for the above dates on Hotelwatchdog.