Direct flights from Portland to Chicago
- 7 flights a week
- Southwest Airlines
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When the nonstops leave
Typical weekly schedule · 7 flights per week · Updated 80d ago
Most leave in the morning.
Arrive the same day
6:45 AMSun
7:40 AM5 days a week
Arrive the same day
3:55 PMSat
No nonstop leaves after 6 PM.
Southwest Airlines
Frequently asked questions
Is there a direct flight from Portland to Chicago?
Yes. Southwest Airlines flies nonstop from Portland (PWM) to Chicago (MDW), daily. The flight takes about 2h 21m and covers 893 miles (1,437 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 ~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 days of the week are there direct flights from Portland to Chicago?
Direct flights from Portland to Chicago operate every day of the week.