Direct flights from Portland to Chicago PDX → MDW

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

Southwest Airlines WN

Departure Schedule next 7 days

More nonstops from Portland

PDX → ANC Anchorage 2 airlines PDX → ATL Atlanta 2 airlines PDX → ABQ Albuquerque 2 airlines PDX → AMS Amsterdam PDX → ATW Appleton PDX → DEN Denver 4 airlines PDX → LAX Los Angeles 4 airlines PDX → LAS Las Vegas 3 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 ~3h 31m (approximately 2811 km).

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