Southwest Airlines flights from Orlando (MCO) to Midway, Chicago (MDW).

Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Sat 14:30 Orlando (MCO) 18:20 Midway, Chicago (MDW)
Southwest Airlines WN 1786 1-stop Boeing 737-800 (73H) 4:50 Effective 2025-01-11 through 2025-02-08
Sat 16:25 Orlando (MCO) 20:10 Midway, Chicago (MDW)
Southwest Airlines WN 1786 1-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2025-02-15 through 2025-03-01
Mon-Wed 17:30 Orlando (MCO) 20:35 Midway, Chicago (MDW)
Southwest Airlines WN 1980 1-stop Boeing 737-700 (73W) 4:05 Effective 2024-11-26 through 2024-12-02
Mon,Thu,Fri,Sun 17:30 Orlando (MCO) 20:35 Midway, Chicago (MDW)
Southwest Airlines WN 1980 1-stop Boeing 737-700 (73W) 4:05 Effective 2024-12-20 through 2025-01-02
Sun 17:30 Orlando (MCO) 20:35 Midway, Chicago (MDW)
Southwest Airlines WN 1980 1-stop Boeing 737-700 (73W) 4:05 Operates only on 2025-01-05
Sat 14:25 Orlando (MCO) 17:45 Midway, Chicago (MDW)
Southwest Airlines WN 2050 1-stop Boeing 737-700 (73W) 4:20 Effective 2024-11-09 through 2024-11-16
Sat 14:25 Orlando (MCO) 17:45 Midway, Chicago (MDW)
Southwest Airlines WN 2050 1-stop Boeing 737-700 (73W) 4:20 Effective 2024-12-07 through 2024-12-14
Sat 14:30 Orlando (MCO) 17:35 Midway, Chicago (MDW)
Southwest Airlines WN 2316 1-stop Boeing 737-700 (73W) 4:05 Valid until 2024-09-28
Sun 16:30 Orlando (MCO) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 2431 1-stop Boeing 737-700 (73W) 4:00 Effective 2024-09-08 through 2024-09-29
Thu 07:00 Orlando (MCO) 11:05 Midway, Chicago (MDW)
Southwest Airlines WN 2496 1-stop Boeing 737-700 (73W) 5:05 Operates only on 2024-10-31
Sat 10:35 Orlando (MCO) 14:10 Midway, Chicago (MDW)
Southwest Airlines WN 2710 1-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2024-11-09 through 2024-11-16
Sat 10:35 Orlando (MCO) 14:10 Midway, Chicago (MDW)
Southwest Airlines WN 2710 1-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2024-12-07 through 2024-12-14
Sat 12:30 Orlando (MCO) 16:00 Midway, Chicago (MDW)
Southwest Airlines WN 2756 1-stop Boeing 737-700 (73W) 4:30 Effective 2025-01-11 through 2025-02-08
Sat 14:45 Orlando (MCO) 18:10 Midway, Chicago (MDW)
Southwest Airlines WN 2756 1-stop Boeing 737-700 (73W) 4:25 Effective 2024-11-09 through 2024-11-16
Sat 14:45 Orlando (MCO) 18:10 Midway, Chicago (MDW)
Southwest Airlines WN 2756 1-stop Boeing 737-700 (73W) 4:25 Effective 2024-12-07 through 2024-12-14
Sun 08:05 Orlando (MCO) 12:25 Midway, Chicago (MDW)
Southwest Airlines WN 2758 1-stop Boeing 737 MAX 8 (7M8) 5:20 Operates only on 2024-09-01
Sun 09:00 Orlando (MCO) 13:05 Midway, Chicago (MDW)
Southwest Airlines WN 2847 1-stop Boeing 737-700 (73W) 5:05 Operates only on 2024-12-01
Sat 15:10 Orlando (MCO) 19:10 Midway, Chicago (MDW)
Southwest Airlines WN 3044 1-stop Boeing 737-700 (73W) 5:00 Effective 2024-11-09 through 2024-11-16
Sat 15:10 Orlando (MCO) 19:10 Midway, Chicago (MDW)
Southwest Airlines WN 3044 1-stop Boeing 737-700 (73W) 5:00 Effective 2024-12-07 through 2024-12-14
Mon-Wed 09:00 Orlando (MCO) 12:50 Midway, Chicago (MDW)
Southwest Airlines WN 3094 1-stop Boeing 737-700 (73W) 4:50 Effective 2024-11-04 through 2024-11-06
Tue,Wed 09:00 Orlando (MCO) 12:50 Midway, Chicago (MDW)
Southwest Airlines WN 3094 1-stop Boeing 737-700 (73W) 4:50 Effective 2024-11-12 through 2024-11-20
Tue-Fri 09:00 Orlando (MCO) 12:50 Midway, Chicago (MDW)
Southwest Airlines WN 3094 1-stop Boeing 737-700 (73W) 4:50 Effective 2024-11-29 through 2024-12-06
Mon-Thu 09:00 Orlando (MCO) 12:50 Midway, Chicago (MDW)
Southwest Airlines WN 3094 1-stop Boeing 737-700 (73W) 4:50 Effective 2024-12-09 through 2024-12-18
Tue,Wed 09:00 Orlando (MCO) 12:50 Midway, Chicago (MDW)
Southwest Airlines WN 3094 1-stop Boeing 737-700 (73W) 4:50 Effective 2024-12-24 through 2025-01-01
Mon 09:00 Orlando (MCO) 12:50 Midway, Chicago (MDW)
Southwest Airlines WN 3094 1-stop Boeing 737-700 (73W) 4:50 Operates only on 2025-01-06
Sat 14:55 Orlando (MCO) 18:20 Midway, Chicago (MDW)
Southwest Airlines WN 3122 1-stop Boeing 737-700 (73W) 4:25 Effective 2024-11-09 through 2024-11-16
Sat 14:55 Orlando (MCO) 18:20 Midway, Chicago (MDW)
Southwest Airlines WN 3122 1-stop Boeing 737-700 (73W) 4:25 Effective 2024-12-07 through 2024-12-14
Sun 10:15 Orlando (MCO) 14:20 Midway, Chicago (MDW)
Southwest Airlines WN 3226 1-stop Boeing 737-800 (73H) 5:05 Operates only on 2024-12-01
Sat 15:45 Orlando (MCO) 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 3259 1-stop Boeing 737-700 (73W) 4:10 Effective 2025-02-15 through 2025-03-01
Sat 15:20 Orlando (MCO) 18:25 Midway, Chicago (MDW)
Southwest Airlines WN 3547 1-stop Boeing 737-700 (73W) 4:05 Effective 2024-11-09 through 2024-11-16
Sat 15:20 Orlando (MCO) 18:25 Midway, Chicago (MDW)
Southwest Airlines WN 3547 1-stop Boeing 737-700 (73W) 4:05 Effective 2024-12-07 through 2024-12-14
Sun 18:20 Orlando (MCO) 22:30 Midway, Chicago (MDW)
Southwest Airlines WN 3549 1-stop Boeing 737-700 (73W) 5:10 Effective 2024-09-08 through 2024-09-29
Sun 17:05 Orlando (MCO) 21:45 Midway, Chicago (MDW)
Southwest Airlines WN 3593 1-stop Boeing 737-700 (73W) 5:40 Effective 2024-09-08 through 2024-09-29
Mon-Wed 15:50 Orlando (MCO) 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 3655 1-stop Boeing 737-700 (73W) 4:05 Effective 2024-11-04 through 2024-11-06
Tue,Wed 15:50 Orlando (MCO) 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 3655 1-stop Boeing 737-700 (73W) 4:05 Effective 2024-11-12 through 2024-11-20
Tue-Fri 15:50 Orlando (MCO) 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 3655 1-stop Boeing 737-700 (73W) 4:05 Effective 2024-11-29 through 2024-12-06
Mon-Thu 15:50 Orlando (MCO) 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 3655 1-stop Boeing 737-700 (73W) 4:05 Effective 2024-12-09 through 2024-12-18
Tue,Wed 15:50 Orlando (MCO) 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 3655 1-stop Boeing 737-700 (73W) 4:05 Effective 2024-12-24 through 2025-01-01
Mon 15:50 Orlando (MCO) 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 3655 1-stop Boeing 737-700 (73W) 4:05 Operates only on 2025-01-06
Sat 15:55 Orlando (MCO) 19:55 Midway, Chicago (MDW)
Southwest Airlines WN 3754 1-stop Boeing 737-700 (73W) 5:00 Effective 2025-02-15 through 2025-03-01
Sat 09:55 Orlando (MCO) 14:05 Midway, Chicago (MDW)
Southwest Airlines WN 3848 1-stop Boeing 737-700 (73W) 5:10 Valid until 2024-09-28
Thu,Fri,Sun 10:00 Orlando (MCO) 14:25 Midway, Chicago (MDW)
Southwest Airlines WN 3890 1-stop Boeing 737-800 (73H) 5:25 Effective 2024-11-03 through 2024-11-10
Mon,Thu,Fri,Sun 10:00 Orlando (MCO) 14:25 Midway, Chicago (MDW)
Southwest Airlines WN 3890 1-stop Boeing 737-800 (73H) 5:25 Effective 2024-11-11 through 2024-11-25
Fri,Sun 10:00 Orlando (MCO) 14:25 Midway, Chicago (MDW)
Southwest Airlines WN 3890 1-stop Boeing 737-800 (73H) 5:25 Effective 2024-12-08 through 2024-12-15
Thu 10:00 Orlando (MCO) 14:25 Midway, Chicago (MDW)
Southwest Airlines WN 3890 1-stop Boeing 737-800 (73H) 5:25 Operates only on 2024-12-19
Fri 10:00 Orlando (MCO) 14:25 Midway, Chicago (MDW)
Southwest Airlines WN 3890 1-stop Boeing 737-800 (73H) 5:25 Operates only on 2025-01-03
Sat 14:20 Orlando (MCO) 17:50 Midway, Chicago (MDW)
Southwest Airlines WN 4165 1-stop Boeing 737-700 (73W) 4:30 Effective 2025-01-11 through 2025-02-08
Sun 07:00 Orlando (MCO) 11:15 Midway, Chicago (MDW)
Southwest Airlines WN 4258 1-stop Boeing 737-700 (73W) 5:15 Operates only on 2024-12-01
Sun 16:00 Orlando (MCO) 19:55 Midway, Chicago (MDW)
Southwest Airlines WN 4298 1-stop Boeing 737-700 (73W) 4:55 Effective 2024-10-06 through 2024-10-27
Sun 09:35 Orlando (MCO) 13:10 Midway, Chicago (MDW)
Southwest Airlines WN 4322 1-stop Boeing 737-700 (73W) 4:35 Effective 2024-10-06 through 2024-10-27
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Southwest Airlines flights from Orlando (MCO) to Midway, Chicago (MDW).
Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:

Effective 2025-01-11 through 2025-02-08
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:50, 1-stop
Boeing 737-800 (73H)

Effective 2025-02-15 through 2025-03-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:45, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-11-26 through 2024-12-02
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-20 through 2025-01-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-01-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-09 through 2024-11-16
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-07 through 2024-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (73W)

Valid until 2024-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:00, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-10-31
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 5:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-09 through 2024-11-16
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:35, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-12-07 through 2024-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:35, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-01-11 through 2025-02-08
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:30, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-09 through 2024-11-16
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:25, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-07 through 2024-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:25, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-09-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:20, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-09 through 2024-11-16
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:00, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-07 through 2024-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:00, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-04 through 2024-11-06
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-12 through 2024-11-20
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-29 through 2024-12-06
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-09 through 2024-12-18
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-24 through 2025-01-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-01-06
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-09 through 2024-11-16
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:25, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-07 through 2024-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:25, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:05, 1-stop
Boeing 737-800 (73H)

Effective 2025-02-15 through 2025-03-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:10, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-09 through 2024-11-16
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-07 through 2024-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:40, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-04 through 2024-11-06
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-12 through 2024-11-20
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-29 through 2024-12-06
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-09 through 2024-12-18
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-24 through 2025-01-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-01-06
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2025-02-15 through 2025-03-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:00, 1-stop
Boeing 737-700 (73W)

Valid until 2024-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-03 through 2024-11-10
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 5:25, 1-stop
Boeing 737-800 (73H)

Effective 2024-11-11 through 2024-11-25
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 5:25, 1-stop
Boeing 737-800 (73H)

Effective 2024-12-08 through 2024-12-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 5:25, 1-stop
Boeing 737-800 (73H)

Operates only on 2024-12-19
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 5:25, 1-stop
Boeing 737-800 (73H)

Operates only on 2025-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 5:25, 1-stop
Boeing 737-800 (73H)

Effective 2025-01-11 through 2025-02-08
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:30, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:15, 1-stop
Boeing 737-700 (73W)

Effective 2024-10-06 through 2024-10-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:55, 1-stop
Boeing 737-700 (73W)

Effective 2024-10-06 through 2024-10-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:35, 1-stop
Boeing 737-700 (73W)
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  • A domestic route departing from the Orlando airport (MCO) and arriving at Midway, Chicago airport (MDW).
  • The flight distance is 990 miles, or 1593 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 2:40 and 3:00.