Airlines with flights from Portland to Chicago

There are three airlines with scheduled flights between PDX and MDW. Southwest is the only airline with non-stop flights from Portland International to Midway International Airport and the flight time is 3 hours and 55 minutes.

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Schedules

Non-stop with Southwest Airlines

  • Total flight time: 3 hours and 55 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 7 flights per week
PDX
Direct
MDW
 
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SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

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

Via Denver with Southwest Airlines

  • Total flight time: 5h 25m - 10h 00m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 21 flights per week
PDX
 
Via DEN
 
MDW
 
Flight
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SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

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

Via Minneapolis with Delta Air Lines

  • Total flight time: 5h 51m - 7h 56m.
  • Sky Team Alliance
  • 14 flights per week
PDX
 
Via MSP
 
MDW
 
Flight
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SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

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

Via Sacramento with Southwest Airlines

  • Total flight time: 6h 00m - 10h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 7 flights per week
PDX
 
Via SMF
 
MDW
 
Flight
Mon
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Jan 6
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Jan 7
SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

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

Via Denver with Frontier Airlines

  • Total flight time: 5h 35m - 7h 47m.
  • Low-cost airline
  • Chicago is a Frontier Airlines focus city.
  • 3 flights per week
PDX
 
Via DEN
 
MDW
 
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
SHOW RETURN SCHEDULE
CHECK PRICES FOR PDX - MDW

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

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