Nonstop flights from Portland to Chicago

Southwest Airlines flies this route daily until Oct 30.

PWMPortland International Jetport

892 mi · 7 flights a week

MDWChicago Midway International

PWMMDW

When they leave

Portland time

7:40a5:15pFirst departure 7:40 AM, last 5:15 PM

One morning flight at 7:40 AM, then one afternoon flight at 3:45 PM, then one evening flight at 5:15 PM.

Every flight

Earliest first

7:40 AM→9:10 AMSouthwest AirlinesUntil Oct 30Boeing 737-700Mon, Tue, Wed, Thu, Fri
3:45 PM→5:20 PMSouthwest AirlinesUntil Oct 30Boeing 737 MAX 8Sat
5:15 PM→6:45 PMSouthwest AirlinesUntil Oct 30Boeing 737Sun

Schedules last checked Sep 8, 2026. Times are local.

Flying from Portland to Chicago

Southwest Airlines is the only airline flying nonstop from Portland to Chicago, daily on the Boeing 737, Boeing 737 MAX 8 and Boeing 737-700.

The first arrival in Chicago is at 9:10 AM and the last at 6:45 PM. The flight covers 892 miles.

Flying back, Chicago to Portland has 7 nonstop flights a week. From Portland, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 42 a week.