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

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Tue,Wed 16:15 Orlando (MCO) 18:00 Midway, Chicago (MDW)
Southwest Airlines WN 2037 Non-stop Boeing 737-700 (73W) 2:45 Effective 2024-10-08 through 2024-10-30
Sun 16:45 Orlando (MCO) 18:35 Midway, Chicago (MDW)
Southwest Airlines WN 2037 Non-stop Boeing 737-700 (73W) 2:50 Effective 2024-10-06 through 2024-10-27
Sat 16:55 Orlando (MCO) 18:45 Midway, Chicago (MDW)
Southwest Airlines WN 2037 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-10-05 through 2024-11-02
Thu 14:25 Orlando (MCO) 16:10 Midway, Chicago (MDW)
Southwest Airlines WN 2049 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Operates only on 2024-10-31
Mon,Thu,Fri 16:00 Orlando (MCO) 17:50 Midway, Chicago (MDW)
Southwest Airlines WN 2049 Non-stop Boeing 737-800 (73H) 2:50 Effective 2024-10-03 through 2024-10-28
Fri 16:00 Orlando (MCO) 17:50 Midway, Chicago (MDW)
Southwest Airlines WN 2049 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2024-11-01
Sun 19:55 Orlando (MCO) 21:45 Midway, Chicago (MDW)
Southwest Airlines WN 2091 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2024-12-01
Mon-Wed 20:05 Orlando (MCO) 21:55 Midway, Chicago (MDW)
Southwest Airlines WN 2091 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-11-26 through 2024-12-02
Mon,Thu,Fri,Sun 20:05 Orlando (MCO) 21:55 Midway, Chicago (MDW)
Southwest Airlines WN 2091 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-12-20 through 2025-01-02
Sun 20:05 Orlando (MCO) 21:55 Midway, Chicago (MDW)
Southwest Airlines WN 2091 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2025-01-05
Sun 09:20 Orlando (MCO) 11:10 Midway, Chicago (MDW)
Southwest Airlines WN 2235 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2024-12-01
Thu 06:25 Orlando (MCO) 08:20 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Operates only on 2024-11-28
Mon-Wed 17:25 Orlando (MCO) 19:15 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-11-04 through 2024-11-06
Tue,Wed 17:25 Orlando (MCO) 19:15 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-11-12 through 2024-11-20
Tue-Fri 17:25 Orlando (MCO) 19:15 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-11-29 through 2024-12-06
Mon-Thu 17:25 Orlando (MCO) 19:15 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-12-09 through 2024-12-18
Tue,Wed 17:25 Orlando (MCO) 19:15 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-12-24 through 2025-01-01
Mon 17:25 Orlando (MCO) 19:15 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2025-01-06
Thu,Fri,Sun 17:40 Orlando (MCO) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-11-03 through 2024-11-10
Mon,Thu,Fri,Sun 17:40 Orlando (MCO) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-11-11 through 2024-11-25
Fri,Sun 17:40 Orlando (MCO) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-12-08 through 2024-12-15
Thu 17:40 Orlando (MCO) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2024-12-19
Fri 17:40 Orlando (MCO) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2025-01-03
Mon,Thu,Fri,Sun 17:40 Orlando (MCO) 19:40 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2025-02-13 through 2025-02-17
Thu,Fri,Sun 17:40 Orlando (MCO) 19:40 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2025-02-21 through 2025-03-02
Mon-Fri 17:45 Orlando (MCO) 19:45 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-800 (73H) 3:00 Effective 2025-01-07 through 2025-01-15
Tue-Fri,Sun 17:45 Orlando (MCO) 19:45 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-800 (73H) 3:00 Effective 2025-01-19 through 2025-01-24
Mon-Fri 17:45 Orlando (MCO) 19:45 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-800 (73H) 3:00 Effective 2025-01-27 through 2025-02-05
Tue,Wed,Sun 17:45 Orlando (MCO) 19:45 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-800 (73H) 3:00 Effective 2025-02-09 through 2025-02-12
Tue,Wed 17:45 Orlando (MCO) 19:45 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-800 (73H) 3:00 Effective 2025-02-19 through 2025-03-05
Thu,Fri,Sun 18:35 Orlando (MCO) 20:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-700 (73W) 2:55 Effective 2025-01-12 through 2025-01-17
Mon,Sun 18:35 Orlando (MCO) 20:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-700 (73W) 2:55 Effective 2025-01-20 through 2025-01-26
Thu,Fri,Sun 18:35 Orlando (MCO) 20:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-700 (73W) 2:55 Effective 2025-02-02 through 2025-02-07
Mon 18:35 Orlando (MCO) 20:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-700 (73W) 2:55 Operates only on 2025-02-10
Mon,Tue,Thu 18:35 Orlando (MCO) 20:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-700 (73W) 2:55 Effective 2025-02-18 through 2025-02-24
Mon 18:35 Orlando (MCO) 20:30 Midway, Chicago (MDW)
Southwest Airlines WN 2401 Non-stop Boeing 737-700 (73W) 2:55 Operates only on 2025-03-03
Sun 08:15 Orlando (MCO) 10:00 Midway, Chicago (MDW)
Southwest Airlines WN 2493 Non-stop Boeing 737-800 (73H) 2:45 Operates only on 2024-10-27
Sun 08:55 Orlando (MCO) 10:45 Midway, Chicago (MDW)
Southwest Airlines WN 2493 Non-stop Boeing 737-800 (73H) 2:50 Effective 2024-10-06 through 2024-10-20
Sat 09:20 Orlando (MCO) 11:10 Midway, Chicago (MDW)
Southwest Airlines WN 2493 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2024-10-05 through 2024-11-02
Thu 17:15 Orlando (MCO) 19:05 Midway, Chicago (MDW)
Southwest Airlines WN 2603 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2024-10-31
Thu 21:20 Orlando (MCO) 23:00 Midway, Chicago (MDW)
Southwest Airlines WN 2603 Non-stop Boeing 737-800 (73H) 2:40 Operates only on 2024-10-03
Mon,Thu,Fri 21:30 Orlando (MCO) 23:10 Midway, Chicago (MDW)
Southwest Airlines WN 2603 Non-stop Boeing 737-800 (73H) 2:40 Effective 2024-10-04 through 2024-10-28
Fri 21:30 Orlando (MCO) 23:10 Midway, Chicago (MDW)
Southwest Airlines WN 2603 Non-stop Boeing 737-800 (73H) 2:40 Operates only on 2024-11-01
Sun 21:55 Orlando (MCO) 23:35 Midway, Chicago (MDW)
Southwest Airlines WN 2603 Non-stop Boeing 737-800 (73H) 2:40 Effective 2024-10-06 through 2024-10-27
Sun 18:50 Orlando (MCO) 20:35 Midway, Chicago (MDW)
Southwest Airlines WN 2665 Non-stop Boeing 737-700 (73W) 2:45 Effective 2024-09-08 through 2024-09-29
Sat 19:40 Orlando (MCO) 21:25 Midway, Chicago (MDW)
Southwest Airlines WN 2665 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Valid until 2024-09-28
Mon-Fri 20:05 Orlando (MCO) 21:50 Midway, Chicago (MDW)
Southwest Airlines WN 2665 Non-stop Boeing 737-800 (73H) 2:45 Valid until 2024-10-02
Thu 10:45 Orlando (MCO) 12:30 Midway, Chicago (MDW)
Southwest Airlines WN 2670 Non-stop Boeing 737-800 (73H) 2:45 Operates only on 2024-10-31
Tue,Wed 11:05 Orlando (MCO) 12:55 Midway, Chicago (MDW)
Southwest Airlines WN 2670 Non-stop Boeing 737-700 (73W) 2:50 Effective 2024-10-08 through 2024-10-30
Mon,Thu,Fri 12:40 Orlando (MCO) 14:25 Midway, Chicago (MDW)
Southwest Airlines WN 2670 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2024-10-03 through 2024-10-28
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Southwest Airlines flights from Orlando (MCO) to Midway, Chicago (MDW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2024-10-08 through 2024-10-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:45, non-stop
Boeing 737-700 (73W)

Effective 2024-10-06 through 2024-10-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737-700 (73W)

Effective 2024-10-05 through 2024-11-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-10-31
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:45, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-11-26 through 2024-12-02
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-12-20 through 2025-01-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-01-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Operates only on 2024-11-28
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:55, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-11-04 through 2024-11-06
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-11-12 through 2024-11-20
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-11-29 through 2024-12-06
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-12-09 through 2024-12-18
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-12-24 through 2025-01-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-01-06
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-11-03 through 2024-11-10
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-11-11 through 2024-11-25
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-12-08 through 2024-12-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-12-19
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-02-13 through 2025-02-17
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 3:00, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-02-21 through 2025-03-02
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 3:00, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-01-07 through 2025-01-15
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 3:00, non-stop
Boeing 737-800 (73H)

Effective 2025-01-19 through 2025-01-24
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
Duration: 3:00, non-stop
Boeing 737-800 (73H)

Effective 2025-01-27 through 2025-02-05
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 3:00, non-stop
Boeing 737-800 (73H)

Effective 2025-02-09 through 2025-02-12
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:00, non-stop
Boeing 737-800 (73H)

Effective 2025-02-19 through 2025-03-05
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:00, non-stop
Boeing 737-800 (73H)

Effective 2025-01-12 through 2025-01-17
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:55, non-stop
Boeing 737-700 (73W)

Effective 2025-01-20 through 2025-01-26
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:55, non-stop
Boeing 737-700 (73W)

Effective 2025-02-02 through 2025-02-07
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:55, non-stop
Boeing 737-700 (73W)

Operates only on 2025-02-10
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:55, non-stop
Boeing 737-700 (73W)

Effective 2025-02-18 through 2025-02-24
Mon
Tue
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:55, non-stop
Boeing 737-700 (73W)

Operates only on 2025-03-03
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:55, non-stop
Boeing 737-700 (73W)

Operates only on 2024-10-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:45, non-stop
Boeing 737-800 (73H)

Effective 2024-10-06 through 2024-10-20
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2024-10-05 through 2024-11-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-10-31
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-10-03
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:40, non-stop
Boeing 737-800 (73H)

Effective 2024-10-04 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:40, non-stop
Boeing 737-800 (73H)

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 2:40, non-stop
Boeing 737-800 (73H)

Effective 2024-10-06 through 2024-10-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:40, non-stop
Boeing 737-800 (73H)

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:45, non-stop
Boeing 737-700 (73W)

Valid until 2024-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:45, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2024-10-02
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 2:45, non-stop
Boeing 737-800 (73H)

Operates only on 2024-10-31
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:45, non-stop
Boeing 737-800 (73H)

Effective 2024-10-08 through 2024-10-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-700 (73W)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:45, non-stop
Boeing 737 MAX 8 (7M8)
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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.