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All scheduled flights from Chicago to Portland (MDW-PDX)

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United States US
All scheduled flights from MDW to PDX. You can fly from Chicago to Portland non-stop on Mondays, Thursdays & Fridays and the flight takes about 4 hours and 20 minutes. Flights with stops take between 6 to 9 hours depending on your flight and connection airport.
MDW-PDX
- Flight has a long layover time at the stop-airport and will affect your flight time.
- Change of terminals at the layover airport. This can go quickly or take time depending on the airport.
- Flight is partially or completely overnight (Red-eye flight).
- Airline or one of the airlines in the flight path is a low-cost carrier. Some travelers wants to avoid low-cost airlines.
- This is codeshare flight. A codeshare flight is an agreement between airlines to sell seats on each others flights. Click on the flight to see the actual flight operator.

Flying non-stop between MDW and PDX with Southwest Airlines is the fastest option. The flight takes about 4 hours and 25 minutes. Second fastest options is landing at MSP with a total flight time of 5 hours and 58 minutes.

PDX is the IATA airport code for Portland International Airport, Portland, Oregon.

The transfer from PDX is 18 minutes by car to Downtown Portland and 19 minutes with car to Downtown Portland.

Airlines that offer direct flights from Chicago (MDW) to Portland (PDX) is Southwest Airlines.

The Boeing 737-800 Passenger with Southwest Airlines has 159 seats and the Boeing 737-800 (winglets) Passenger/BBJ2 with Southwest Airlines has 159 seats.

It all depends on what dates you plan on flying. But the approximate round-trip price for one passenger with Southwest is $529.