Nonstop flights from Portland to Chicago

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

PDXPortland International

1,747 mi · 17 flights a week

MDWChicago Midway International

PDXMDW

When they leave

Portland time

6:15a11:30pFirst departure 6:15 AM, last 11:30 PM

Four in the morning, 6:15 AM to 11:35 AM, then one evening flight at 11:30 PM.

Every flight

Earliest first

6:15 AM→12:10 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Tue, Wed, Thu, Fri
7:35 AM→1:35 PMSouthwest AirlinesBoeing 737Sat
10:55 AM→4:55 PMSouthwest AirlinesBoeing 737Sun
11:35 AM→5:35 PMSouthwest AirlinesBoeing 737Mon, Thu, Fri
11:30 PM→5:25 AM⁺¹Southwest AirlinesBoeing 737 MAX 8Daily

Schedules last checked Sep 19, 2026. Times are local.

Flying from Portland to Chicago

Southwest Airlines is the only airline flying nonstop from Portland to Chicago, 2 to 3 times a day on the Boeing 737 and 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 Chicago is at 12:10 PM and the last at 5:25 AM the next day. The flight covers 1,747 miles.

Flying back, Chicago to Portland has 17 nonstop flights a week. From Portland, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 70 a week.