All airlines flying from Midway, Chicago (MDW) to Orlando (MCO).

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Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Sun 14:55 Midway, Chicago (MDW) 21:10 Orlando (MCO)
Southwest Airlines WN 436 1-stop Boeing 737 MAX 8 (7M8) 5:15 Operates only on 2025-06-01
Sun 08:05 Midway, Chicago (MDW) 13:55 Orlando (MCO)
Southwest Airlines WN 546 1-stop Boeing 737-700 (73W) 4:50 Effective 2025-08-10 through 2025-08-24
Sun 08:05 Midway, Chicago (MDW) 13:55 Orlando (MCO)
Southwest Airlines WN 546 1-stop Boeing 737-700 (73W) 4:50 Effective 2025-09-07 through 2025-09-28
Mon,Thu,Fri 17:50 Midway, Chicago (MDW) 22:55 Orlando (MCO)
Southwest Airlines WN 644 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-10-02 through 2025-10-31
Sun 07:55 Midway, Chicago (MDW) 12:45 Orlando (MCO)
Southwest Airlines WN 967 1-stop Boeing 737-700 (Scimitar Winglets) 3:50 Effective 2025-10-05 through 2025-10-26
Sat 07:20 Midway, Chicago (MDW) 13:05 Orlando (MCO)
Southwest Airlines WN 990 1-stop Boeing 737-700 (Scimitar Winglets) 4:45 Effective 2025-10-04 through 2025-11-01
Sun 10:45 Midway, Chicago (MDW) 16:25 Orlando (MCO)
Southwest Airlines WN 996 1-stop Boeing 737-700 (73W) 4:40 Operates only on 2025-08-31
Sun 09:05 Midway, Chicago (MDW) 14:10 Orlando (MCO)
Southwest Airlines WN 1073 1-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-06-08 through 2025-08-03
Mon-Wed 07:45 Midway, Chicago (MDW) 13:50 Orlando (MCO)
Southwest Airlines WN 1186 1-stop Boeing 737-800 (73H) 5:05 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 07:45 Midway, Chicago (MDW) 13:50 Orlando (MCO)
Southwest Airlines WN 1186 1-stop Boeing 737-800 (73H) 5:05 Effective 2025-12-19 through 2026-01-04
Sun 07:35 Midway, Chicago (MDW) 12:45 Orlando (MCO)
Southwest Airlines WN 1646 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Operates only on 2025-11-30
Mon,Thu,Fri 05:50 Midway, Chicago (MDW) 12:00 Orlando (MCO)
Southwest Airlines WN 1706 1-stop Boeing 737 MAX 8 (7M8) 5:10 Valid until 2025-06-02
Mon-Wed 15:55 Midway, Chicago (MDW) 21:05 Orlando (MCO)
Southwest Airlines WN 1874 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 15:55 Midway, Chicago (MDW) 21:05 Orlando (MCO)
Southwest Airlines WN 1874 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2025-12-19 through 2026-01-04
Sat 15:00 Midway, Chicago (MDW) 21:15 Orlando (MCO)
Southwest Airlines WN 1902 1-stop Boeing 737 MAX 8 (7M8) 5:15 Effective 2025-11-22 through 2025-11-29
Sat 15:00 Midway, Chicago (MDW) 21:15 Orlando (MCO)
Southwest Airlines WN 1902 1-stop Boeing 737 MAX 8 (7M8) 5:15 Effective 2025-12-20 through 2026-01-03
Mon,Thu,Fri 09:35 Midway, Chicago (MDW) 14:50 Orlando (MCO)
Southwest Airlines WN 2010 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Effective 2025-10-02 through 2025-10-31
Mon,Thu,Fri,Sun 17:00 Midway, Chicago (MDW) 22:05 Orlando (MCO)
Southwest Airlines WN 2030 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 17:00 Midway, Chicago (MDW) 22:05 Orlando (MCO)
Southwest Airlines WN 2030 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-11-21 through 2025-11-28
Fri,Sun 17:00 Midway, Chicago (MDW) 22:05 Orlando (MCO)
Southwest Airlines WN 2030 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-12-07 through 2025-12-14
Thu 17:00 Midway, Chicago (MDW) 22:05 Orlando (MCO)
Southwest Airlines WN 2030 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Operates only on 2025-12-18
Mon 17:00 Midway, Chicago (MDW) 22:05 Orlando (MCO)
Southwest Airlines WN 2030 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Operates only on 2026-01-05
Mon-Wed 07:50 Midway, Chicago (MDW) 14:20 Orlando (MCO)
Southwest Airlines WN 2099 1-stop Boeing 737-700 (Scimitar Winglets) 5:30 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 07:50 Midway, Chicago (MDW) 14:20 Orlando (MCO)
Southwest Airlines WN 2099 1-stop Boeing 737-700 (Scimitar Winglets) 5:30 Effective 2025-12-19 through 2026-01-04
Mon,Thu,Fri 08:35 Midway, Chicago (MDW) 14:25 Orlando (MCO)
Southwest Airlines WN 2140 1-stop Boeing 737-800 (73H) 4:50 Valid until 2025-06-02
Thu 09:00 Midway, Chicago (MDW) 14:15 Orlando (MCO)
Southwest Airlines WN 2190 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Operates only on 2025-11-27
Tue,Wed 10:00 Midway, Chicago (MDW) 16:25 Orlando (MCO)
Southwest Airlines WN 2234 1-stop Boeing 737 MAX 8 (7M8) 5:25 Effective 2025-08-05 through 2025-10-01
Mon-Wed 05:25 Midway, Chicago (MDW) 12:00 Orlando (MCO)
Southwest Airlines WN 2464 1-stop Boeing 737-700 (Scimitar Winglets) 5:35 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 05:25 Midway, Chicago (MDW) 12:00 Orlando (MCO)
Southwest Airlines WN 2464 1-stop Boeing 737-700 (Scimitar Winglets) 5:35 Effective 2025-12-19 through 2026-01-04
Fri 08:20 Midway, Chicago (MDW) 14:30 Orlando (MCO)
Southwest Airlines WN 2623 1-stop Boeing 737-700 (73W) 5:10 Operates only on 2025-07-04
Mon,Thu,Fri 14:35 Midway, Chicago (MDW) 21:15 Orlando (MCO)
Southwest Airlines WN 2675 1-stop Boeing 737-700 (73W) 5:40 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 14:35 Midway, Chicago (MDW) 21:15 Orlando (MCO)
Southwest Airlines WN 2675 1-stop Boeing 737-700 (73W) 5:40 Effective 2025-07-07 through 2025-08-04
Sun 10:05 Midway, Chicago (MDW) 15:50 Orlando (MCO)
Southwest Airlines WN 2679 1-stop Boeing 737-700 (73W) 4:45 Effective 2025-08-10 through 2025-08-24
Sun 10:05 Midway, Chicago (MDW) 15:50 Orlando (MCO)
Southwest Airlines WN 2679 1-stop Boeing 737-700 (73W) 4:45 Effective 2025-09-07 through 2025-09-28
Tue,Wed 13:25 Midway, Chicago (MDW) 18:45 Orlando (MCO)
Southwest Airlines WN 2791 1-stop Boeing 737-700 (73W) 4:20 Effective 2025-08-05 through 2025-10-01
Sun 13:55 Midway, Chicago (MDW) 19:15 Orlando (MCO)
Southwest Airlines WN 2791 1-stop Boeing 737-800 (73H) 4:20 Operates only on 2025-08-31
Mon,Thu,Fri,Sun 09:30 Midway, Chicago (MDW) 14:45 Orlando (MCO)
Southwest Airlines WN 2825 1-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 09:30 Midway, Chicago (MDW) 14:45 Orlando (MCO)
Southwest Airlines WN 2825 1-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2025-11-21 through 2025-11-28
Fri,Sun 09:30 Midway, Chicago (MDW) 14:45 Orlando (MCO)
Southwest Airlines WN 2825 1-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2025-12-07 through 2025-12-14
Thu 09:30 Midway, Chicago (MDW) 14:45 Orlando (MCO)
Southwest Airlines WN 2825 1-stop Boeing 737 MAX 8 (7M8) 4:15 Operates only on 2025-12-18
Mon 09:30 Midway, Chicago (MDW) 14:45 Orlando (MCO)
Southwest Airlines WN 2825 1-stop Boeing 737 MAX 8 (7M8) 4:15 Operates only on 2026-01-05
Sat 09:55 Midway, Chicago (MDW) 15:15 Orlando (MCO)
Southwest Airlines WN 2825 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-11-08 through 2025-11-15
Sat 09:55 Midway, Chicago (MDW) 15:15 Orlando (MCO)
Southwest Airlines WN 2825 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-12-06 through 2025-12-13
Sun 09:55 Midway, Chicago (MDW) 15:40 Orlando (MCO)
Southwest Airlines WN 2842 1-stop Boeing 737-700 (73W) 4:45 Effective 2025-06-08 through 2025-08-03
Sat 12:30 Midway, Chicago (MDW) 18:30 Orlando (MCO)
Southwest Airlines WN 2910 1-stop Boeing 737-700 (Scimitar Winglets) 5:00 Effective 2025-11-08 through 2025-11-15
Sat 12:30 Midway, Chicago (MDW) 18:30 Orlando (MCO)
Southwest Airlines WN 2910 1-stop Boeing 737-700 (Scimitar Winglets) 5:00 Effective 2025-12-06 through 2025-12-13
Tue,Wed 13:10 Midway, Chicago (MDW) 19:55 Orlando (MCO)
Southwest Airlines WN 2912 1-stop Boeing 737 MAX 8 (7M8) 5:45 Effective 2025-10-07 through 2025-10-29
Fri 09:55 Midway, Chicago (MDW) 15:40 Orlando (MCO)
Southwest Airlines WN 2927 1-stop Boeing 737-800 (73H) 4:45 Operates only on 2025-07-04
Mon,Thu,Fri 13:50 Midway, Chicago (MDW) 19:40 Orlando (MCO)
Southwest Airlines WN 2927 1-stop Boeing 737 MAX 8 (7M8) 4:50 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 13:50 Midway, Chicago (MDW) 19:40 Orlando (MCO)
Southwest Airlines WN 2927 1-stop Boeing 737 MAX 8 (7M8) 4:50 Effective 2025-07-07 through 2025-08-04
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All airlines flying from Midway, Chicago (MDW) to Orlando (MCO).
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Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:15, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Effective 2025-10-02 through 2025-10-31
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-05 through 2025-10-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:50, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-04 through 2025-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-08-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:40, 1-stop
Boeing 737-700 (73W)

Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:05, 1-stop
Boeing 737-800 (73H)

Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 5:05, 1-stop
Boeing 737-800 (73H)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:10, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:15, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:15, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-10-02 through 2025-10-31
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 5:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737-800 (73H)

Operates only on 2025-11-27
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-08-05 through 2025-10-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:25, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:35, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 5:35, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-07-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:40, 1-stop
Boeing 737-700 (73W)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:40, 1-stop
Boeing 737-700 (73W)

Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:45, 1-stop
Boeing 737-700 (73W)

Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:45, 1-stop
Boeing 737-700 (73W)

Effective 2025-08-05 through 2025-10-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-08-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:20, 1-stop
Boeing 737-800 (73H)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 4:15, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:15, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:15, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:15, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:15, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:45, 1-stop
Boeing 737-700 (73W)

Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-07 through 2025-10-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:45, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-07-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 4:45, 1-stop
Boeing 737-800 (73H)

Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737 MAX 8 (7M8)
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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 2:51.