Portland→ChicagoNonstop Flight TimePDX–MDW

Portland (Portland International Airport) to Chicago (Chicago Midway International Airport).

Direct flights from PDX to MDW have an estimated flight time of about 4h 11m, based on the 1,747-mile great-circle distance. Our current captured departure sample includes 2-3/day across 1 captured airline, with Southwest Airlines appearing most often in that sample. Captured departure times run from 05:10 to 23:30 local time.

Methodology: airline, aircraft, terminal, and departure-time details come from the rolling scheduled-departures window for PDX to MDW, last seen June 15, 2026. Frequency uses 18 scheduled departures across 7 observed days; flight time is estimated from great-circle distance until this route has enough tracked flights for an observed average. Provider coverage can miss operators on some routes, so confirm live timetables before booking.