Fly nonstop from Portland to Chicago for $264 round-trip on Southwest.
Seen below, we found seats departing PDX on Wednesday, November 4, returning from MDW on Sunday, November 8.
Other dates are available for travel from October 3 through December 13.
For booking info, see our Fare Details.
Need a room in Chicago? Here's what's available for the above dates on Hotelwatchdog.