Direct flights from Portland to Chicago
- ~2 flights a day
- Southwest Airlines
🔔 Track this route
We check PDX → MDW every day and email you the cheapest nonstop fares we find.
Free · one-click unsubscribe
When the nonstops leave
Typical weekly schedule · 17 flights per week (~2 per day) · Updated 80d ago
Most leave in the morning.
Arrive the same day
5:10 AMSun
6:00 AMMon, Thu, Fri
6:05 AMSat
11:50 AM5 days a week
No nonstop leaves between noon and 6 PM.
Arrive the next morning
11:30 PM
Southwest Airlines
Frequently asked questions
Is there a direct flight from Portland to Chicago?
Yes. Southwest Airlines flies nonstop from Portland (PDX) to Chicago (MDW), daily. The flight takes about 4h 6m and covers 1,747 miles (2,811 km). Schedule data from 30 July 2026.
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 ~4h 6m (approximately 2811 km).
How often do direct flights operate from Portland to Chicago?
Nonstop flights from Portland to Chicago operate daily — 17 flights per week (~2 per day).
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.