Airlines with flights from Portland to Chicago

There are two airlines with scheduled flights between PWM and MDW. Southwest is the only airline with non-stop flights from Portland International Jetport to Midway International Airport and the flight time is 2 hours and 35 minutes.

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Schedules

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 35 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 1 flight per week
PWM
Direct
MDW

The timetable & schedule information was updated at 2024-12-13

Via Baltimore with Southwest Airlines

  • Total flight time: 4h 20m - 8h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 17 flights per week
PWM
 
Via BWI
 
MDW

The timetable & schedule information was updated at 2024-12-13

Via Detroit with Delta Air Lines

  • Total flight time: 4h 25m - 5h 25m.
  • Sky Team Alliance
  • 7 flights per week
PWM
 
Via DTW
 
MDW

The timetable & schedule information was updated at 2024-12-13

Via Nashville with Southwest Airlines

  • Total flight time: 5h 45m - 8h 40m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 3 flights per week
PWM
 
Via BNA
 
MDW

The timetable & schedule information was updated at 2024-12-13

Via Minneapolis with Delta Air Lines

  • Total flight time: 7h 25m - 7h 39m.
  • Sky Team Alliance
PWM
 
Via MSP
 
MDW

The timetable & schedule information was updated at 2024-12-13

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