Direct flights from Portland to Chicago
All flights from PDX to MDW non-stop. There are direct flights from Portland International, Oregon, USA to Chicago Midway International (MDW), Illinois, USA every day of the week with Southwest Airlines. The flight distance is 1756 miles and the trip usually takes about 3 hours and 55 minutes.
Portland , USA
Chicago , USA
Airlines with non-stop routes:
Southwest AirlinesLow-cost airline
Flight schedule from Portland to Chicago with Southwest Airlines
This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
The timetable & schedule information was updated at 2023-03-20
Return flight schedule from Chicago to Portland with Southwest Airlines
Portland to Chicago flight departures
Select a date to see all scheduled flight departures between PDX to MDW.
PDX - MDW information
Distance1756 miles (2825 km)
Flight time3 hours and 55 minutes
AlliancesOne WorldSky TeamStar Alliance
Southwest AircraftBoeing 737 Passenger