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

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sat 07:50 Portland (PDX) 13:45 Midway, Chicago (MDW)
Southwest Airlines WN 423 Non-stop Boeing 737-700 (73W) 3:55 Effective 2024-11-23 through 2024-11-30
Sat 07:50 Portland (PDX) 13:45 Midway, Chicago (MDW)
Southwest Airlines WN 423 Non-stop Boeing 737-700 (73W) 3:55 Effective 2024-12-21 through 2025-01-04
Sun 06:30 Portland (PDX) 12:25 Midway, Chicago (MDW)
Southwest Airlines WN 648 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2024-12-01
Tue,Wed 06:15 Portland (PDX) 12:15 Midway, Chicago (MDW)
Southwest Airlines WN 835 Non-stop Boeing 737-800 (73H) 4:00 Valid until 2024-10-02
Mon,Thu,Fri 09:05 Portland (PDX) 15:00 Midway, Chicago (MDW)
Southwest Airlines WN 967 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Valid until 2024-09-30
Mon,Thu,Fri 06:00 Portland (PDX) 12:00 Midway, Chicago (MDW)
Southwest Airlines WN 1489 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Valid until 2024-09-30
Sun 11:05 Portland (PDX) 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 1944 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2024-09-01
Sat 05:50 Portland (PDX) 11:50 Midway, Chicago (MDW)
Southwest Airlines WN 2014 Non-stop Boeing 737-800 (73H) 4:00 Valid until 2024-09-28
Mon,Thu,Fri 05:45 Portland (PDX) 11:40 Midway, Chicago (MDW)
Southwest Airlines WN 2069 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2024-10-03 through 2024-10-28
Fri 05:45 Portland (PDX) 11:40 Midway, Chicago (MDW)
Southwest Airlines WN 2069 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2024-11-01
Tue,Wed 06:10 Portland (PDX) 12:05 Midway, Chicago (MDW)
Southwest Airlines WN 2069 Non-stop Boeing 737-800 (73H) 3:55 Effective 2024-10-08 through 2024-10-30
Sun 06:35 Portland (PDX) 12:30 Midway, Chicago (MDW)
Southwest Airlines WN 2069 Non-stop Boeing 737-800 (73H) 3:55 Effective 2024-10-06 through 2024-10-27
Thu 07:35 Portland (PDX) 13:30 Midway, Chicago (MDW)
Southwest Airlines WN 2069 Non-stop Boeing 737-700 (73W) 3:55 Operates only on 2024-10-31
Sat 09:50 Portland (PDX) 15:45 Midway, Chicago (MDW)
Southwest Airlines WN 2069 Non-stop Boeing 737-800 (73H) 3:55 Effective 2024-10-05 through 2024-11-02
Sun 07:00 Portland (PDX) 13:00 Midway, Chicago (MDW)
Southwest Airlines WN 2426 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Operates only on 2024-09-01
Sun 13:35 Portland (PDX) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 2426 Non-stop Boeing 737-800 (73H) 3:55 Effective 2024-09-08 through 2024-09-29
Tue,Wed 15:00 Portland (PDX) 20:55 Midway, Chicago (MDW)
Southwest Airlines WN 2426 Non-stop Boeing 737-700 (73W) 3:55 Valid until 2024-10-02
Mon,Thu,Fri 13:45 Portland (PDX) 19:35 Midway, Chicago (MDW)
Southwest Airlines WN 2658 Non-stop Boeing 737-700 (73W) 3:50 Valid until 2024-09-30
Sat 10:00 Portland (PDX) 15:55 Midway, Chicago (MDW)
Southwest Airlines WN 2995 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Valid until 2024-09-28
Tue,Wed 10:40 Portland (PDX) 16:35 Midway, Chicago (MDW)
Southwest Airlines WN 2995 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Valid until 2024-10-02
Thu 06:20 Portland (PDX) 12:15 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2024-11-28
Thu,Fri,Sun 06:25 Portland (PDX) 12:20 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Effective 2024-11-03 through 2024-11-10
Mon,Thu,Fri,Sun 06:25 Portland (PDX) 12:20 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Effective 2024-11-11 through 2024-11-25
Fri,Sun 06:25 Portland (PDX) 12:20 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Effective 2024-12-08 through 2024-12-15
Thu 06:25 Portland (PDX) 12:20 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Operates only on 2024-12-19
Fri 06:25 Portland (PDX) 12:20 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Operates only on 2025-01-03
Sat 06:35 Portland (PDX) 12:30 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2024-11-09 through 2024-11-16
Sat 06:35 Portland (PDX) 12:30 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2024-12-07 through 2024-12-14
Mon,Thu-Sun 06:35 Portland (PDX) 12:30 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-02-13 through 2025-02-17
Thu-Sun 06:35 Portland (PDX) 12:30 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-02-21 through 2025-03-02
Thu,Fri,Sun 08:00 Portland (PDX) 13:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-01-12 through 2025-01-17
Mon,Sun 08:00 Portland (PDX) 13:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-01-20 through 2025-01-26
Thu,Fri,Sun 08:00 Portland (PDX) 13:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-02-02 through 2025-02-07
Mon 08:00 Portland (PDX) 13:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2025-02-10
Mon,Tue,Thu 08:00 Portland (PDX) 13:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-02-18 through 2025-02-24
Mon 08:00 Portland (PDX) 13:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2025-03-03
Mon-Fri 09:00 Portland (PDX) 14:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-01-07 through 2025-01-15
Sat 09:00 Portland (PDX) 14:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-01-11 through 2025-02-08
Tue-Fri,Sun 09:00 Portland (PDX) 14:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-01-19 through 2025-01-24
Mon-Fri 09:00 Portland (PDX) 14:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-01-27 through 2025-02-05
Tue,Wed,Sun 09:00 Portland (PDX) 14:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-02-09 through 2025-02-12
Tue,Wed 09:00 Portland (PDX) 14:55 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-02-19 through 2025-03-05
Mon-Wed 11:30 Portland (PDX) 17:25 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2024-11-04 through 2024-11-06
Tue,Wed 11:30 Portland (PDX) 17:25 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2024-11-12 through 2024-11-20
Tue-Fri 11:30 Portland (PDX) 17:25 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2024-11-29 through 2024-12-06
Mon-Thu 11:30 Portland (PDX) 17:25 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2024-12-09 through 2024-12-18
Tue,Wed 11:30 Portland (PDX) 17:25 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2024-12-24 through 2025-01-01
Mon 11:30 Portland (PDX) 17:25 Midway, Chicago (MDW)
Southwest Airlines WN 3049 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2025-01-06
Tue,Wed 11:15 Portland (PDX) 17:10 Midway, Chicago (MDW)
Southwest Airlines WN 3191 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2024-10-08 through 2024-10-30
Mon,Thu,Fri 13:05 Portland (PDX) 19:00 Midway, Chicago (MDW)
Southwest Airlines WN 3191 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2024-10-03 through 2024-10-28
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Southwest Airlines flights from Portland (PDX) to Midway, Chicago (MDW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2024-11-23 through 2024-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737-700 (73W)

Effective 2024-12-21 through 2025-01-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737-700 (73W)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2024-10-02
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:00, non-stop
Boeing 737-800 (73H)

Valid until 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-09-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2024-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, non-stop
Boeing 737-800 (73H)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-10-08 through 2024-10-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2024-10-06 through 2024-10-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Operates only on 2024-10-31
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-700 (73W)

Effective 2024-10-05 through 2024-11-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Operates only on 2024-09-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Valid until 2024-10-02
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-700 (73W)

Valid until 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:50, non-stop
Boeing 737-700 (73W)

Valid until 2024-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2024-10-02
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-11-28
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-11-03 through 2024-11-10
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2024-11-11 through 2024-11-25
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2024-12-08 through 2024-12-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Operates only on 2024-12-19
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Operates only on 2025-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2024-11-09 through 2024-11-16
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-12-07 through 2024-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-02-13 through 2025-02-17
Mon
Tue
-
Wed
-
Thu
Fri
Sat
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2025-02-21 through 2025-03-02
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2025-01-12 through 2025-01-17
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-01-20 through 2025-01-26
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-02-02 through 2025-02-07
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-02-10
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-02-18 through 2025-02-24
Mon
Tue
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-03-03
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-01-07 through 2025-01-15
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2025-01-11 through 2025-02-08
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-01-19 through 2025-01-24
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2025-01-27 through 2025-02-05
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2025-02-09 through 2025-02-12
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2025-02-19 through 2025-03-05
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Effective 2024-11-04 through 2024-11-06
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-11-12 through 2024-11-20
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-11-29 through 2024-12-06
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-12-09 through 2024-12-18
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-12-24 through 2025-01-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-01-06
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-10-08 through 2024-10-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)
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  • A domestic route departing from the Portland airport (PDX) and arriving at Midway, Chicago airport (MDW).
  • The flight distance is 1745 miles, or 2809 km.
  • The timezone of the departure airport is UTC-8 , 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 3:50 and 4:00.