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

Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Mon,Tue,Fri,Sun 09:30 Midway, Chicago (MDW) 15:25 Orlando (MCO)
Southwest Airlines WN 4498 1-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2025-12-22 through 2026-01-05
Sat 11:15 Midway, Chicago (MDW) 16:35 Orlando (MCO)
Southwest Airlines WN 4506 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-11-22 through 2025-11-29
Sat 11:15 Midway, Chicago (MDW) 16:35 Orlando (MCO)
Southwest Airlines WN 4506 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-12-20 through 2026-01-03
Sun 14:40 Midway, Chicago (MDW) 19:55 Orlando (MCO)
Southwest Airlines WN 4883 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Operates only on 2025-11-30
Sun 12:20 Midway, Chicago (MDW) 20:40 Orlando (MCO)
Southwest Airlines WN 2108 2-stop Boeing 737-700 (Scimitar Winglets) 7:20 Operates only on 2025-11-30
Mon,Thu,Fri 12:30 Midway, Chicago (MDW) 20:30 Orlando (MCO)
Southwest Airlines WN 2145 2-stop Boeing 737-700 (73W) 7:00 Valid until 2025-06-02
Sat 09:50 Midway, Chicago (MDW) 17:10 Orlando (MCO)
Southwest Airlines WN 2825 2-stop Boeing 737-700 (Scimitar Winglets) 6:20 Effective 2025-11-22 through 2025-11-29
Sat 09:50 Midway, Chicago (MDW) 17:10 Orlando (MCO)
Southwest Airlines WN 2825 2-stop Boeing 737-700 (Scimitar Winglets) 6:20 Effective 2025-12-20 through 2026-01-03
Sat 09:25 Midway, Chicago (MDW) 16:45 Orlando (MCO)
Southwest Airlines WN 3963 2-stop Boeing 737-700 (73W) 6:20 Effective 2025-06-07 through 2025-08-02
Sat 09:25 Midway, Chicago (MDW) 19:40 Orlando (MCO)
Southwest Airlines WN 2993 3-stop Boeing 737-700 (Scimitar Winglets) 9:15 Effective 2025-11-08 through 2025-11-15
Sat 09:25 Midway, Chicago (MDW) 19:40 Orlando (MCO)
Southwest Airlines WN 2993 3-stop Boeing 737-700 (Scimitar Winglets) 9:15 Effective 2025-12-06 through 2025-12-13
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Southwest Airlines flights from Midway, Chicago (MDW) to Orlando (MCO).
Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:

Effective 2025-12-22 through 2026-01-05
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:55, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 7:20, 2-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 7:00, 2-stop
Boeing 737-700 (73W)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:20, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:20, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-06-07 through 2025-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:20, 2-stop
Boeing 737-700 (73W)

Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 9:15, 3-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 9:15, 3-stop
Boeing 737-700 (Scimitar Winglets)
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  • A domestic route departing from the Midway, Chicago airport (MDW) and arriving at Orlando airport (MCO).
  • The flight distance is 990 miles, or 1593 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 2:30 and 2:50.