Direct flights from Chicago to Portland

MDW - PDX route map All flights from MDW to PDX non-stop. There are direct flights from Chicago Midway International, Illinois, USA to Portland International (PDX), Oregon, USA every day of the week with Southwest Airlines. The flight distance is 1756 miles and the trip usually takes about 4 hours and 20 minutes.

MDW
Chicago Midway
USAChicago , USA
PDX
Portland International
USAPortland , USA
MDW
Chicago Midway
USAChicago , USA
Portland
USAPortland , USA
PDX
Flight time is 4 hours and 20 minutes
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Airlines with non-stop routes:

Southwest Airlines

S
M
T
W
T
F
S
Low-cost airline
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1 flight per day
1 flight per day
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
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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
Mon
May 12
Tue
May 13
Wed
May 14
Thu
May 15
Fri
May 16
Sat
May 17
Sun
May 18
WN2765
16:15
16:30
16:30
16:15
16:15
16:15
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WN4217
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22:15

The timetable & schedule information was updated at 2025-04-22

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Chicago to Portland flight departures

Select a date to see all scheduled flight departures between MDW to PDX.

Friday
Fri
May 09
1 flights(1)
Saturday
Sat
May 10
1 flights(1)
Sunday
Sun
May 11
1 flights(1)
Monday
Mon
May 12
1 flights(1)
Tuesday
Tue
May 13
1 flights(1)
Wednesday
Wed
May 14
1 flights(1)
Thursday
Thu
May 15
1 flights(1)
Time
Airline
Flight
16:15
Southwest Airlines Southwest Airlines
WN2765
16:15
Southwest Airlines Southwest Airlines
WN2765
22:15
Southwest Airlines Southwest Airlines
WN4217
16:15
Southwest Airlines Southwest Airlines
WN2765
16:30
Southwest Airlines Southwest Airlines
WN2765
16:30
Southwest Airlines Southwest Airlines
WN2765
16:15
Southwest Airlines Southwest Airlines
WN2765
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MDW-PDX flight route
Chicago, MDW to Portland, PDX flight path. The distance is 1756 miles or 2825 km.
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Chicago - Portland direct flight map
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MDW - PDX information

  • Distance
    1756 miles (2825 km)
  • Flight time
    4 hours and 20 minutes
  • Airlines
    Southwest Southwest
  • Alliances
    One World
    Sky Team
    Star Alliance
  • Classes
    Economy
    Business
    First Class
  • Southwest Aircraft
    Boeing 737 Passenger
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Yes. You can fly direct to Portland (PDX) every day with Southwest Airlines.

The flight time is 4 hours and 20 minutes. The distance is 1756 miles or 2825 kilometers.

There are approximately 5 flights every week with departures between 07:45 and 22:25.

No, there are no direct flights from Chicago to Portland with Star Alliance.

No, there are no direct flights from Chicago to Portland with oneworld.

No, there are no direct flights from Chicago to Portland with SkyTeam.

Southwest flies this route with the Boeing 737 Passenger aircraft.

Southwest have non-stop flights to Portland.

You can fly direct every day of the week.