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.

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