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

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 21:30 Midway, Chicago (MDW) 23:55 Portland (PDX)
Southwest Airlines WN 3860 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2025-10-02 through 2025-10-31
Fri 08:30 Midway, Chicago (MDW) 10:55 Portland (PDX)
Southwest Airlines WN 3874 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Operates only on 2025-07-04
Mon,Thu,Fri 09:10 Midway, Chicago (MDW) 11:30 Portland (PDX)
Southwest Airlines WN 3874 Non-stop Boeing 737-700 (73W) 4:20 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 09:10 Midway, Chicago (MDW) 11:30 Portland (PDX)
Southwest Airlines WN 3874 Non-stop Boeing 737-700 (73W) 4:20 Effective 2025-07-07 through 2025-08-04
Tue,Wed 21:30 Midway, Chicago (MDW) 23:55 Portland (PDX)
Southwest Airlines WN 3874 Non-stop Boeing 737-700 (73W) 4:25 Effective 2025-06-10 through 2025-07-30
Tue,Wed 07:45 Midway, Chicago (MDW) 10:05 Portland (PDX)
Southwest Airlines WN 4004 Non-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-10-07 through 2025-10-29
Sun 21:00 Midway, Chicago (MDW) 23:20 Portland (PDX)
Southwest Airlines WN 4109 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Operates only on 2025-05-25
Sun 22:15 Midway, Chicago (MDW) 00:35 Portland (PDX)
Southwest Airlines WN 4217 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Valid until 2025-05-18
The flight arrives 1 day after departure.
Sun 22:15 Midway, Chicago (MDW) 00:35 Portland (PDX)
Southwest Airlines WN 4217 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Operates only on 2025-06-01
The flight arrives 1 day after departure.
Non-Direct Flights:
Sun 08:10 Midway, Chicago (MDW) 13:35 Portland (PDX)
Southwest Airlines WN 3851 1-stop Boeing 737 MAX 8 (7M8) 7:25 Effective 2025-06-08 through 2025-08-03
Mon,Thu,Fri 06:15 Midway, Chicago (MDW) 12:55 Portland (PDX)
Southwest Airlines WN 969 2-stop Boeing 737-700 (73W) 8:40 Valid until 2025-06-02
Tue,Wed 12:35 Midway, Chicago (MDW) 20:40 Portland (PDX)
Southwest Airlines WN 482 3-stop Boeing 737-700 (73W) 10:05 Valid until 2025-06-04
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All airlines flying from Midway, Chicago (MDW) to Portland (PDX).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2025-10-02 through 2025-10-31
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-07-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:20, non-stop
Boeing 737-700 (73W)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:20, non-stop
Boeing 737-700 (73W)

Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:25, non-stop
Boeing 737-700 (73W)

Effective 2025-10-07 through 2025-10-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Non-Direct Flights:

Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 7:25, 1-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 8:40, 2-stop
Boeing 737-700 (73W)

Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 10:05, 3-stop
Boeing 737-700 (73W)
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  • A domestic route departing from the Midway, Chicago airport (MDW) and arriving at Portland airport (PDX).
  • The flight distance is 1745 miles, or 2809 km.
  • The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-8 . 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 4:10 and 4:35.