Direct flights from Portland to Chicago PDX → MDW
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). Arrivals run on time 81.8% at PDX 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.
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Southwest Airlines
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Departure Schedule typical week
Typical weekly schedule · 17 flights per week (~2 per day) · 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 (PDX) 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 ~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 is the on-time performance for flights from Portland to Chicago?
Arrivals run on time 81.8% at PDX 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.
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