Direct flights from Chicago to Portland
All flights from MDW to PDX non-stop. There are direct flights from Chicago Midway International (MDW), Illinois, USA to Portland International (PDX), Oregon, USA with Southwest Airlines. 17 weekly departures are currently scheduled on this route. Departure times range from 09:35 to 22:55 depending on the schedule period. The flight distance is 1756 miles (2825 km). Flight time ranges from 4 hours and 10 minutes to 4 hours and 40 minutes.
Chicago
, USA
Flight schedule from Chicago to Portland 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.
Flight
The timetable & schedule information was updated at 2026-08-24
Chicago to Portland scheduled departures
Select a date to see every published non-stop departure between MDW and PDX.
MDW - PDX route facts
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Distance1756 miles (2825 km)
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Flight time4 hours and 10 minutes to 4 hours and 40 minutes
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Airline Southwest
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Airline alliancesLow-cost carrier
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CabinsEconomy
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AircraftBoeing 737MAX 8 Passenger and Boeing 737-700 Passenger (Scimitar Winglets)
