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

FLIGHT SCHEDULE
Direct Flights:
Sun 09:05 Midway, Chicago (MDW) 12:15 Portland (PWM) Southwest Airlines WN 356 Non-stop Boeing 737-700 (73W) 2:10 Effective 2025-06-08 through 2025-08-03
Sat 09:15 Midway, Chicago (MDW) 12:30 Portland (PWM) Southwest Airlines WN 356 Non-stop Boeing 737-700 (73W) 2:15 Effective 2025-06-07 through 2025-08-02
Mon,Thu,Fri 09:20 Midway, Chicago (MDW) 12:35 Portland (PWM) Southwest Airlines WN 356 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 09:20 Midway, Chicago (MDW) 12:35 Portland (PWM) Southwest Airlines WN 356 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-07-07 through 2025-08-04
Tue,Wed 09:45 Midway, Chicago (MDW) 13:00 Portland (PWM) Southwest Airlines WN 356 Non-stop Boeing 737-700 (73W) 2:15 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 10:55 Midway, Chicago (MDW) 14:05 Portland (PWM) Southwest Airlines WN 447 Non-stop Boeing 737-700 (Scimitar Winglets) 2:10 Effective 2025-10-02 through 2025-10-31
Sat 11:20 Midway, Chicago (MDW) 14:30 Portland (PWM) Southwest Airlines WN 447 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2025-10-04 through 2025-11-01
Sun 13:30 Midway, Chicago (MDW) 16:40 Portland (PWM) Southwest Airlines WN 447 Non-stop Boeing 737-800 (73H) 2:10 Effective 2025-10-05 through 2025-10-26
Tue,Wed 13:40 Midway, Chicago (MDW) 16:50 Portland (PWM) Southwest Airlines WN 447 Non-stop Boeing 737-700 (Scimitar Winglets) 2:10 Effective 2025-10-07 through 2025-10-29
Tue,Wed 11:40 Midway, Chicago (MDW) 14:55 Portland (PWM) Southwest Airlines WN 682 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-08-05 through 2025-10-01
Sat 12:50 Midway, Chicago (MDW) 16:05 Portland (PWM) Southwest Airlines WN 682 Non-stop Boeing 737-800 (73H) 2:15 Effective 2025-08-09 through 2025-09-27
Mon,Thu,Fri 13:50 Midway, Chicago (MDW) 17:05 Portland (PWM) Southwest Airlines WN 682 Non-stop Boeing 737-700 (73W) 2:15 Effective 2025-08-07 through 2025-09-29
Sun 17:55 Midway, Chicago (MDW) 21:15 Portland (PWM) Southwest Airlines WN 682 Non-stop Boeing 737-700 (73W) 2:20 Operates only on 2025-08-31
Sun 19:10 Midway, Chicago (MDW) 22:25 Portland (PWM) Southwest Airlines WN 682 Non-stop Boeing 737-700 (73W) 2:15 Effective 2025-08-10 through 2025-08-24
Sun 19:10 Midway, Chicago (MDW) 22:25 Portland (PWM) Southwest Airlines WN 682 Non-stop Boeing 737-700 (73W) 2:15 Effective 2025-09-07 through 2025-09-28
Fri 13:10 Midway, Chicago (MDW) 16:20 Portland (PWM) Southwest Airlines WN 2308 Non-stop Boeing 737-700 (73W) 2:10 Operates only on 2025-07-04
Non-Direct Flights:
Sat 17:25 Midway, Chicago (MDW) 22:25 Portland (PWM) Southwest Airlines WN 1908 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2025-10-04 through 2025-11-01

A domestic route departing from the Midway, Chicago 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 2:10 and 2:20.

Return (PWM-MDW) flights

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN356

09:05

Midway, Chicago (MDW)

12:15

Portland (PWM)

Effective 2025-06-08 through 2025-08-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN356

09:15

Midway, Chicago (MDW)

12:30

Portland (PWM)

Effective 2025-06-07 through 2025-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN356

09:20

Midway, Chicago (MDW)

12:35

Portland (PWM)

Effective 2025-06-05 through 2025-07-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN356

09:20

Midway, Chicago (MDW)

12:35

Portland (PWM)

Effective 2025-07-07 through 2025-08-04

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN356

09:45

Midway, Chicago (MDW)

13:00

Portland (PWM)

Effective 2025-06-10 through 2025-07-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN447

10:55

Midway, Chicago (MDW)

14:05

Portland (PWM)

Effective 2025-10-02 through 2025-10-31

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN447

11:20

Midway, Chicago (MDW)

14:30

Portland (PWM)

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN447

13:30

Midway, Chicago (MDW)

16:40

Portland (PWM)

Effective 2025-10-05 through 2025-10-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN447

13:40

Midway, Chicago (MDW)

16:50

Portland (PWM)

Effective 2025-10-07 through 2025-10-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN682

11:40

Midway, Chicago (MDW)

14:55

Portland (PWM)

Effective 2025-08-05 through 2025-10-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN682

12:50

Midway, Chicago (MDW)

16:05

Portland (PWM)

Effective 2025-08-09 through 2025-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN682

13:50

Midway, Chicago (MDW)

17:05

Portland (PWM)

Effective 2025-08-07 through 2025-09-29

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN682

17:55

Midway, Chicago (MDW)

21:15

Portland (PWM)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN682

19:10

Midway, Chicago (MDW)

22:25

Portland (PWM)

Effective 2025-08-10 through 2025-08-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN682

19:10

Midway, Chicago (MDW)

22:25

Portland (PWM)

Effective 2025-09-07 through 2025-09-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2308

13:10

Midway, Chicago (MDW)

16:20

Portland (PWM)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-700 (73W)

Non-Direct Flights:

Southwest Airlines WN1908

17:25

Midway, Chicago (MDW)

22:25

Portland (PWM)

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

A domestic route departing from the Midway, Chicago 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 2:10 and 2:20.

Return (PWM-MDW) flights

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