Nonstop flights from Chicago to Portland

Southwest Airlines flies this route 2 to 3 times a day.

MDWChicago Midway International

1,747 mi · 17 flights a week

PDXPortland International

MDWPDX

When they leave

Chicago time

10:40a9:20pFirst departure 10:40 AM, last 9:20 PM

One morning flight at 10:40 AM, then three in the evening, 6:30 PM to 9:20 PM.

Every flight

Earliest first

10:40 AM→12:50 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Tue, Wed, Thu, Fri
6:30 PM→8:45 PMSouthwest AirlinesBoeing 737 MAX 8Daily
8:50 PM→11:05 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri, Sat
9:20 PM→11:30 PMSouthwest AirlinesBoeing 737 MAX 8Sun

Schedules last checked Sep 21, 2026. Times are local.

Flying from Chicago to Portland

Southwest Airlines is the only airline flying nonstop from Chicago to Portland, 2 to 3 times a day on the Boeing 737 MAX 8.

Flights run every day of the week, 3 on Mondays, Thursdays and Fridays and 2 on the other days. The first arrival in Portland is at 12:50 PM and the last at 11:30 PM. The flight covers 1,747 miles.

Flying back, Portland to Chicago has 17 nonstop flights a week. O'Hare (ORD) also has nonstop flights to Portland, 72 a week.

Return flights

Portland to ChicagoView

Every Chicago airport

All Chicago to Portland flightsView

Find the cheapest day to fly from Chicago to Portland.

Schedules as of Oct 9, 2026.