All airlines flying from Chicago Midway (MDW) to Portland (PWM).

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Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sat 15:20 Chicago Midway (MDW) 18:35 Portland (PWM)
Southwest Airlines WN 300 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-08-08 through 2026-09-26
Sun 17:55 Chicago Midway (MDW) 21:15 Portland (PWM)
Southwest Airlines WN 300 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-09 through 2026-09-27
Tue,Wed 18:50 Chicago Midway (MDW) 22:05 Portland (PWM)
Southwest Airlines WN 300 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 18:10 Chicago Midway (MDW) 21:30 Portland (PWM)
Southwest Airlines WN 431 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-06 through 2026-09-28
Sat 13:00 Chicago Midway (MDW) 16:15 Portland (PWM)
Southwest Airlines WN 1467 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-06 through 2026-08-01
Tue,Wed 18:15 Chicago Midway (MDW) 21:30 Portland (PWM)
Southwest Airlines WN 4272 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 18:55 Chicago Midway (MDW) 22:10 Portland (PWM)
Southwest Airlines WN 4272 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-04 through 2026-08-03
Sun 19:55 Chicago Midway (MDW) 23:10 Portland (PWM)
Southwest Airlines WN 4272 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-07 through 2026-08-02
Non-Direct Flights:
Mon,Thu,Fri 08:00 Chicago Midway (MDW) 14:15 Portland (PWM)
Southwest Airlines WN 4008 2-stop Boeing 737-700 (Scimitar Winglets) 5:15 Effective 2026-03-05 through 2026-04-06
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Parallax here MDW-PWM


All airlines flying from Chicago Midway (MDW) to Portland (PWM).
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Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2026-08-08 through 2026-09-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-06-06 through 2026-08-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-06-04 through 2026-08-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Effective 2026-03-05 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:15, 2-stop
Boeing 737-700 (Scimitar Winglets)
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Parallax here MDW-PWM
  • A domestic route departing from the Chicago Midway airport (MDW) and arriving at Portland airport (PWM).
  • The flight distance is 893 miles, or 1437 km.
  • The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-5 . 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 2:15 and 2:20.