Southwest Airlines flights from Portland (PWM) to Chicago Midway (MDW).

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sun 06:45 Portland (PWM) 08:20 Chicago Midway (MDW)
Southwest Airlines WN 2464 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-06-07 through 2026-08-02
Sat 15:40 Portland (PWM) 17:15 Chicago Midway (MDW)
Southwest Airlines WN 2751 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-08-08 through 2026-09-26
Mon,Thu,Fri 07:35 Portland (PWM) 09:05 Chicago Midway (MDW)
Southwest Airlines WN 3338 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-08-06 through 2026-09-28
Sun 07:40 Portland (PWM) 09:10 Chicago Midway (MDW)
Southwest Airlines WN 3338 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-08-09 through 2026-09-27
Tue,Wed 07:45 Portland (PWM) 09:20 Chicago Midway (MDW)
Southwest Airlines WN 3338 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-08-04 through 2026-09-30
Tue,Wed 07:30 Portland (PWM) 09:05 Chicago Midway (MDW)
Southwest Airlines WN 3415 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 07:40 Portland (PWM) 09:15 Chicago Midway (MDW)
Southwest Airlines WN 3415 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-06-04 through 2026-08-03
Sat 15:55 Portland (PWM) 17:40 Chicago Midway (MDW)
Southwest Airlines WN 3642 Non-stop Boeing 737-700 (Scimitar Winglets) 2:45 Effective 2026-06-06 through 2026-08-01




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Southwest Airlines flights from Portland (PWM) to Chicago Midway (MDW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Southwest Airlines WN2464
06:45
Portland (PWM)

08:20
Chicago Midway (MDW)
Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737-800 (73H)
Direct Flights:
Southwest Airlines WN2751
15:40
Portland (PWM)

17:15
Chicago Midway (MDW)
Effective 2026-08-08 through 2026-09-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN3338
07:35
Portland (PWM)

09:05
Chicago Midway (MDW)
Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN3338
07:40
Portland (PWM)

09:10
Chicago Midway (MDW)
Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN3338
07:45
Portland (PWM)

09:20
Chicago Midway (MDW)
Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN3415
07:30
Portland (PWM)

09:05
Chicago Midway (MDW)
Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737-800 (73H)
Direct Flights:
Southwest Airlines WN3415
07:40
Portland (PWM)

09:15
Chicago Midway (MDW)
Effective 2026-06-04 through 2026-08-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737-800 (73H)
Direct Flights:
Southwest Airlines WN3642
15:55
Portland (PWM)

17:40
Chicago Midway (MDW)
Effective 2026-06-06 through 2026-08-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:45, non-stop
Boeing 737-700 (Scimitar Winglets)
  • A domestic route departing from the Portland airport (PWM) and arriving at Chicago Midway airport (MDW).
  • The flight distance is 893 miles, or 1437 km.
  • The timezone of the departure airport is UTC-5 , and the timezone of the arrival airport is UTC-6 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
  • For direct flights, the flight time varies between 2:30 and 2:45.
All PWM-MDW flights
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