Nonstop flights from Chicago to Portland
Southwest Airlines flies this route daily until Oct 30.
MDWChicago Midway International
892 mi · 7 flights a week
PWMPortland International Jetport
When they leave
Chicago time6:10p6:50pFirst departure 6:10 PM, last 6:50 PM
Three in the evening, 6:10 PM to 6:50 PM.
Every flight
Earliest first
Schedules last checked Sep 8, 2026. Times are local.
Flying from Chicago to Portland
Southwest Airlines is the only airline flying nonstop from Chicago to Portland, daily on the Boeing 737-700.
The first arrival in Portland is at 9:35 PM and the last at 10:05 PM. The flight covers 892 miles.
Flying back, Portland to Chicago has 7 nonstop flights a week. O'Hare (ORD) also has nonstop flights to Portland, 36 a week.
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Schedules as of Oct 9, 2026.