Chicago (MDW) → Portland (PWM)
Southwest Airlines operates nonstop flights from Chicago (MDW) to Portland (PWM). The nonstop flight takes around ~1h 48m, covering 893 miles (1,437 km). Updated 1 June 2026.
MDW
→
PWM
Round trip
1 adult
Economy
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Frequently asked questions
Is there a direct flight from Chicago to Portland?
Yes, Southwest Airlines operates nonstop flights from Chicago (MDW) to Portland (PWM).
Which airlines fly direct from Chicago to Portland?
Southwest Airlines operates nonstop flights from Chicago to Portland.
How long is the flight from Chicago to Portland?
The nonstop flight from Chicago to Portland takes ~1h 48m (approximately 1437 km).