Direct flights from Portland to Chicago PWM → MDW
Southwest Airlines flies nonstop from Portland (PWM) to Chicago (MDW), daily. The flight takes about 2h 21m and covers 893 miles (1,437 km). Arrivals run on time 76.1% at PWM and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule. Schedule data from 30 July 2026.
🔔 Watch PWM → MDW
We'll run this search daily and email you the cheapest direct fares we find.
Free · checked daily · one-click unsubscribe
Southwest Airlines
WN
Departure Schedule typical week
Typical weekly schedule · 7 flights per week · Updated 31d ago
Southwest Airlines
Frequently asked questions
Is there a direct flight from Portland to Chicago?
Yes, Southwest Airlines operates nonstop flights from Portland (PWM) to Chicago (MDW).
Which airlines fly direct from Portland to Chicago?
Southwest Airlines operates nonstop flights from Portland to Chicago.
How long is the flight from Portland to Chicago?
The nonstop flight from Portland to Chicago takes ~2h 21m (approximately 1437 km).
How often do direct flights operate from Portland to Chicago?
Nonstop flights from Portland to Chicago operate daily — 7 flights per week.
What is the on-time performance for flights from Portland to Chicago?
Arrivals run on time 76.1% at PWM and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule.
What days of the week are there direct flights from Portland to Chicago?
Direct flights from Portland to Chicago operate every day of the week.
Explore More
Scout — our search agent — hunts nonstop fares from Portland every night and pings you when one's worth booking.
Watch it work →