Portland (PWM) → Chicago (MDW)
Southwest Airlines operates nonstop flights from Portland (PWM) to Chicago (MDW). The nonstop flight takes around ~1h 48m, covering 893 miles (1,437 km). Updated 1 June 2026.
PWM
→
MDW
Round trip
1 adult
Economy
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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 ~1h 48m (approximately 1437 km).