Direct flights from Chicago to Portland MDW → PDX
Southwest Airlines operates nonstop flights from Chicago (MDW) to Portland (PDX). The nonstop flight takes around ~3h 31m, covering 1,747 miles (2,811 km). Updated 11 June 2026.
MDW
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PDX
Round trip
1 adult
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Southwest Airlines
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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 (PDX).
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 ~3h 31m (approximately 2811 km).