Airlines with flights from Chicago to Portland

There are two airlines with scheduled flights between MDW and PWM. Southwest is the only airline with non-stop flights from Midway International Airport to Portland International Jetport and the flight time is 2 hours and 15 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 15 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
MDW
Direct
PWM
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN300
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18:50
18:50
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15:20
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WN431
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18:10
18:10
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18:10
WN4272
18:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PWM

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

Southwest Airlines

Via Baltimore with Southwest Airlines

  • Total flight time: 3h 55m - 8h 20m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 139 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via BWI
 
PWM
 
Flight
Mon
Aug 3
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Aug 4
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Aug 5
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Aug 6
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Aug 7
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Aug 8
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Aug 9
WN2687
WN1050
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05:00
WN2687
WN1051
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05:55
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WN961
WN1051
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06:30
06:30
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WN2742
WN1065
07:00
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WN1088
WN1051
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07:10
WN294
WN2014
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07:30
07:30
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WN1156
WN2261
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----
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08:05
08:05
07:40
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WN719
WN2261
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----
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----
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07:45
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WN4723
WN2968
07:45
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WN1267
WN2968
07:45
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WN2664
WN2261
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07:45
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WN758
WN2968
07:50
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WN986
WN294
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08:00
WN232
WN294
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08:05
WN646
WN2261
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08:05
08:05
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WN1695
WN2968
08:05
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WN908
WN294
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08:05
WN1156
WN294
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08:10
WN2809
WN2261
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08:10
08:10
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WN945
WN2261
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08:15
08:15
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WN2809
WN4526
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08:30
08:30
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WN2664
WN4526
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08:30
08:30
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WN1156
WN4526
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08:40
08:40
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WN105
WN4526
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08:45
08:45
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WN1687
WN2261
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09:00
09:00
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WN312
WN2261
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09:05
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WN3666
WN1053
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12:35
12:35
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WN1034
WN1053
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12:45
12:45
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WN1035
WN1053
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13:55
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WN704
WN1467
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14:35
14:35
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WN4832
WN1053
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15:05
15:05
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WN2689
WN1053
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15:45
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WN4616
WN4382
17:20
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WN3292
WN1467
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17:25
17:25
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WN2745
WN4382
19:00
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PWM

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

Southwest Airlines

Via Nashville with Southwest Airlines

  • Total flight time: 4h 30m - 7h 05m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 15 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via BNA
 
PWM
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN508
WN1989
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05:55
05:55
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WN2959
WN651
07:15
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WN1409
WN3239
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07:40
07:40
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WN2676
WN3239
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08:05
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WN442
WN3239
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08:50
WN1257
WN651
09:00
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PWM

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

Delta Air Lines

Via Detroit with Delta Air Lines

  • Total flight time: 5h 30m - 5h 45m.
  • Sky Team Alliance
  • 21 flights per week
MDW
 
Via DTW
 
PWM
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
DL4674
DL1821
09:20
09:20
09:20
09:20
09:20
09:20
09:20
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PWM

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

Southwest Airlines

Via Raleigh/Durham with Southwest Airlines

  • Total flight time: 8h 05m - 8h 05m.
  • 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
MDW
 
Via RDU
 
PWM
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN852
WN2968
07:40
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----
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----
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PWM

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

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Flight data on this page was last updated on 2026-07-13
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