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

Southwest Airlines

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).
  • 7 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
PWM
Direct
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3338
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07:45
07:45
07:40
07:40
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07:40
WN3415
07:40
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WN2751
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15:40
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SHOW RETURN SCHEDULE
CHECK PRICES FOR PWM - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Baltimore with Southwest Airlines

  • Total flight time: 4h 15m - 8h 45m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 116 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
PWM
 
Via BWI
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN4674
WN4217
05:35
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WN3335
WN4094
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05:40
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WN3335
WN992
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05:55
05:55
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WN3335
WN1683
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06:10
WN1097
WN4094
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07:25
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WN3038
WN164
10:25
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WN4393
WN1195
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10:30
10:30
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WN988
WN1339
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10:30
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WN4393
WN992
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10:30
10:30
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WN4393
WN450
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11:10
WN146
WN425
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13:05
13:05
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WN146
WN1682
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13:05
13:05
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WN1245
WN425
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13:25
WN4912
WN4821
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14:40
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WN920
WN1195
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14:50
14:50
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WN183
WN1039
15:10
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WN3336
WN4094
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15:40
15:40
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WN3414
WN999
17:20
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SHOW RETURN SCHEDULE
CHECK PRICES FOR PWM - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Nashville with Southwest Airlines

  • Total flight time: 5h 00m - 8h 35m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 8 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
PWM
 
Via BNA
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3411
WN2241
13:00
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WN3334
WN576
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14:10
14:10
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WN3334
WN577
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17:15
WN492
WN577
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18:15
18:15
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SHOW RETURN SCHEDULE
CHECK PRICES FOR PWM - MDW

The timetable & schedule information was updated at 2026-04-21

Delta Air Lines

Via Detroit with Delta Air Lines

  • Total flight time: 6h 01m - 6h 12m.
  • Sky Team Alliance
  • 31 flights per week
PWM
 
Via DTW
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
SHOW RETURN SCHEDULE
CHECK PRICES FOR PWM - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Raleigh/Durham with Southwest Airlines

  • Total flight time: 6h 25m - 6h 55m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 3 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
PWM
 
Via RDU
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN183
WN3766
15:10
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SHOW RETURN SCHEDULE
CHECK PRICES FOR PWM - MDW

The timetable & schedule information was updated at 2026-04-21

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Staying up-to-date with the airlines

At Airlineinformation.com you can learn all about the airlines operating around the world together with their destinations and where they operate. You will get a transparent overview of airlines with scheduled flights between any two destinations with non-stop or 1-stop flights regardless of price or availability.
Flight data on this page was last updated on 2026-07-21
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