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

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FLIGHT SCHEDULE
Direct Flights:
Sun 19:55 Midway, Chicago (MDW) 23:30 Orlando (MCO) Southwest Airlines WN 2392 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-08-10 through 2025-08-24
Sun 19:55 Midway, Chicago (MDW) 23:30 Orlando (MCO) Southwest Airlines WN 2392 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-09-07 through 2025-09-28
Mon,Thu,Fri 19:30 Midway, Chicago (MDW) 23:10 Orlando (MCO) Southwest Airlines WN 2483 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 19:30 Midway, Chicago (MDW) 23:10 Orlando (MCO) Southwest Airlines WN 2483 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2025-07-07 through 2025-08-04
Sun 20:45 Midway, Chicago (MDW) 00:20 Orlando (MCO) Southwest Airlines WN 2519 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Valid until 2025-05-18 The flight arrives 1 day after departure.
Sun 20:45 Midway, Chicago (MDW) 00:20 Orlando (MCO) Southwest Airlines WN 2519 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Operates only on 2025-06-01 The flight arrives 1 day after departure.
Sat 09:15 Midway, Chicago (MDW) 12:50 Orlando (MCO) Southwest Airlines WN 2526 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2025-10-04 through 2025-11-01
Tue,Wed 13:10 Midway, Chicago (MDW) 16:45 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-11-04 through 2025-11-12
Mon-Thu 13:10 Midway, Chicago (MDW) 16:45 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-11-17 through 2025-11-20
Mon-Fri 13:10 Midway, Chicago (MDW) 16:45 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-12-02 through 2025-12-11
Mon-Wed 13:10 Midway, Chicago (MDW) 16:45 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-12-15 through 2025-12-17
Wed,Thu 13:10 Midway, Chicago (MDW) 16:45 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-12-24 through 2026-01-01
Sat 16:55 Midway, Chicago (MDW) 20:30 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-11-08 through 2025-11-15
Mon-Wed 16:55 Midway, Chicago (MDW) 20:30 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-11-25 through 2025-12-01
Sat 16:55 Midway, Chicago (MDW) 20:30 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-12-06 through 2025-12-13
Mon,Tue,Fri,Sun 16:55 Midway, Chicago (MDW) 20:30 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-12-19 through 2026-01-04
Mon,Thu,Fri,Sun 17:10 Midway, Chicago (MDW) 20:45 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 17:10 Midway, Chicago (MDW) 20:45 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-11-21 through 2025-11-28
Fri,Sun 17:10 Midway, Chicago (MDW) 20:45 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-12-07 through 2025-12-14
Thu 17:10 Midway, Chicago (MDW) 20:45 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Operates only on 2025-12-18
Mon 17:10 Midway, Chicago (MDW) 20:45 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Operates only on 2026-01-05
Sun 17:40 Midway, Chicago (MDW) 21:15 Orlando (MCO) Southwest Airlines WN 2594 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Operates only on 2025-11-30
Tue,Wed 19:00 Midway, Chicago (MDW) 22:45 Orlando (MCO) Southwest Airlines WN 2628 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 20:55 Midway, Chicago (MDW) 00:35 Orlando (MCO) Southwest Airlines WN 2628 Non-stop Boeing 737-700 (73W) 2:40 Effective 2025-06-05 through 2025-07-03 The flight arrives 1 day after departure.
Mon,Thu,Fri 20:55 Midway, Chicago (MDW) 00:35 Orlando (MCO) Southwest Airlines WN 2628 Non-stop Boeing 737-700 (73W) 2:40 Effective 2025-07-07 through 2025-08-04 The flight arrives 1 day after departure.
Sat 08:50 Midway, Chicago (MDW) 12:30 Orlando (MCO) Southwest Airlines WN 2883 Non-stop Boeing 737-800 (73H) 2:40 Effective 2025-06-07 through 2025-08-02
Mon-Fri 09:00 Midway, Chicago (MDW) 12:40 Orlando (MCO) Southwest Airlines WN 2883 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2025-06-05 through 2025-07-03
Mon-Fri 09:00 Midway, Chicago (MDW) 12:40 Orlando (MCO) Southwest Airlines WN 2883 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2025-07-07 through 2025-08-04
Sun 09:20 Midway, Chicago (MDW) 13:00 Orlando (MCO) Southwest Airlines WN 2883 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2025-06-08 through 2025-08-03
Tue,Wed 09:30 Midway, Chicago (MDW) 13:10 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2025-11-04 through 2025-11-12
Mon-Thu 09:30 Midway, Chicago (MDW) 13:10 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2025-11-17 through 2025-11-20
Mon-Fri 09:30 Midway, Chicago (MDW) 13:10 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2025-12-02 through 2025-12-11
Mon-Wed 09:30 Midway, Chicago (MDW) 13:10 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2025-12-15 through 2025-12-17
Wed,Thu 09:30 Midway, Chicago (MDW) 13:10 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2025-12-24 through 2026-01-01
Sat 11:00 Midway, Chicago (MDW) 14:35 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2025-11-08 through 2025-11-15
Sat 11:00 Midway, Chicago (MDW) 14:35 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2025-12-06 through 2025-12-13
Mon,Thu,Fri,Sun 11:45 Midway, Chicago (MDW) 15:20 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 11:45 Midway, Chicago (MDW) 15:20 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2025-11-21 through 2025-11-28
Fri,Sun 11:45 Midway, Chicago (MDW) 15:20 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2025-12-07 through 2025-12-14
Thu 11:45 Midway, Chicago (MDW) 15:20 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Operates only on 2025-12-18
Mon 11:45 Midway, Chicago (MDW) 15:20 Orlando (MCO) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Operates only on 2026-01-05
Mon,Thu,Fri 07:45 Midway, Chicago (MDW) 11:20 Orlando (MCO) Southwest Airlines WN 2987 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 07:45 Midway, Chicago (MDW) 11:20 Orlando (MCO) Southwest Airlines WN 2987 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-07-07 through 2025-08-04
Fri 08:10 Midway, Chicago (MDW) 11:50 Orlando (MCO) Southwest Airlines WN 2987 Non-stop Boeing 737-700 (73W) 2:40 Operates only on 2025-07-04
Sat 09:15 Midway, Chicago (MDW) 12:50 Orlando (MCO) Southwest Airlines WN 2987 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-11-08 through 2025-11-15
Sat 09:15 Midway, Chicago (MDW) 12:50 Orlando (MCO) Southwest Airlines WN 2987 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-12-06 through 2025-12-13
Tue,Wed 10:40 Midway, Chicago (MDW) 14:15 Orlando (MCO) Southwest Airlines WN 2987 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-11-04 through 2025-11-12
Mon-Thu 10:40 Midway, Chicago (MDW) 14:15 Orlando (MCO) Southwest Airlines WN 2987 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-11-17 through 2025-11-20
Mon-Fri 10:40 Midway, Chicago (MDW) 14:15 Orlando (MCO) Southwest Airlines WN 2987 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-12-02 through 2025-12-11
Mon-Wed 10:40 Midway, Chicago (MDW) 14:15 Orlando (MCO) Southwest Airlines WN 2987 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-12-15 through 2025-12-17

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Parallax here MDW-MCO

1 2 3 4 5 6 7 8 9

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.

Return (MCO-MDW) flights

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

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FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN2392

19:55

Midway, Chicago (MDW)

23:30

Orlando (MCO)

Effective 2025-08-10 through 2025-08-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2392

19:55

Midway, Chicago (MDW)

23:30

Orlando (MCO)

Effective 2025-09-07 through 2025-09-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2483

19:30

Midway, Chicago (MDW)

23:10

Orlando (MCO)

Effective 2025-06-05 through 2025-07-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2483

19:30

Midway, Chicago (MDW)

23:10

Orlando (MCO)

Effective 2025-07-07 through 2025-08-04

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2519

20:45

Midway, Chicago (MDW)

00:20(+1)

Orlando (MCO)

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2519

20:45

Midway, Chicago (MDW)

00:20(+1)

Orlando (MCO)

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2526

09:15

Midway, Chicago (MDW)

12:50

Orlando (MCO)

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2594

13:10

Midway, Chicago (MDW)

16:45

Orlando (MCO)

Effective 2025-11-04 through 2025-11-12

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2594

13:10

Midway, Chicago (MDW)

16:45

Orlando (MCO)

Effective 2025-11-17 through 2025-11-20

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2594

13:10

Midway, Chicago (MDW)

16:45

Orlando (MCO)

Effective 2025-12-02 through 2025-12-11

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2594

13:10

Midway, Chicago (MDW)

16:45

Orlando (MCO)

Effective 2025-12-15 through 2025-12-17

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2594

13:10

Midway, Chicago (MDW)

16:45

Orlando (MCO)

Effective 2025-12-24 through 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2594

16:55

Midway, Chicago (MDW)

20:30

Orlando (MCO)

Effective 2025-11-08 through 2025-11-15

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2594

16:55

Midway, Chicago (MDW)

20:30

Orlando (MCO)

Effective 2025-11-25 through 2025-12-01

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2594

16:55

Midway, Chicago (MDW)

20:30

Orlando (MCO)

Effective 2025-12-06 through 2025-12-13

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2594

16:55

Midway, Chicago (MDW)

20:30

Orlando (MCO)

Effective 2025-12-19 through 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2594

17:10

Midway, Chicago (MDW)

20:45

Orlando (MCO)

Effective 2025-11-02 through 2025-11-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2594

17:10

Midway, Chicago (MDW)

20:45

Orlando (MCO)

Effective 2025-11-21 through 2025-11-28

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2594

17:10

Midway, Chicago (MDW)

20:45

Orlando (MCO)

Effective 2025-12-07 through 2025-12-14

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2594

17:10

Midway, Chicago (MDW)

20:45

Orlando (MCO)

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2594

17:10

Midway, Chicago (MDW)

20:45

Orlando (MCO)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2594

17:40

Midway, Chicago (MDW)

21:15

Orlando (MCO)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2628

19:00

Midway, Chicago (MDW)

22:45

Orlando (MCO)

Effective 2025-06-10 through 2025-07-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2628

20:55

Midway, Chicago (MDW)

00:35(+1)

Orlando (MCO)

Effective 2025-06-05 through 2025-07-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Southwest Airlines WN2628

20:55

Midway, Chicago (MDW)

00:35(+1)

Orlando (MCO)

Effective 2025-07-07 through 2025-08-04

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Southwest Airlines WN2883

08:50

Midway, Chicago (MDW)

12:30

Orlando (MCO)

Effective 2025-06-07 through 2025-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2883

09:00

Midway, Chicago (MDW)

12:40

Orlando (MCO)

Effective 2025-06-05 through 2025-07-03

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2883

09:00

Midway, Chicago (MDW)

12:40

Orlando (MCO)

Effective 2025-07-07 through 2025-08-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2883

09:20

Midway, Chicago (MDW)

13:00

Orlando (MCO)

Effective 2025-06-08 through 2025-08-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2952

09:30

Midway, Chicago (MDW)

13:10

Orlando (MCO)

Effective 2025-11-04 through 2025-11-12

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

09:30

Midway, Chicago (MDW)

13:10

Orlando (MCO)

Effective 2025-11-17 through 2025-11-20

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

09:30

Midway, Chicago (MDW)

13:10

Orlando (MCO)

Effective 2025-12-02 through 2025-12-11

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

09:30

Midway, Chicago (MDW)

13:10

Orlando (MCO)

Effective 2025-12-15 through 2025-12-17

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

09:30

Midway, Chicago (MDW)

13:10

Orlando (MCO)

Effective 2025-12-24 through 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

11:00

Midway, Chicago (MDW)

14:35

Orlando (MCO)

Effective 2025-11-08 through 2025-11-15

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

11:00

Midway, Chicago (MDW)

14:35

Orlando (MCO)

Effective 2025-12-06 through 2025-12-13

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

11:45

Midway, Chicago (MDW)

15:20

Orlando (MCO)

Effective 2025-11-02 through 2025-11-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

11:45

Midway, Chicago (MDW)

15:20

Orlando (MCO)

Effective 2025-11-21 through 2025-11-28

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

11:45

Midway, Chicago (MDW)

15:20

Orlando (MCO)

Effective 2025-12-07 through 2025-12-14

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

11:45

Midway, Chicago (MDW)

15:20

Orlando (MCO)

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2952

11:45

Midway, Chicago (MDW)

15:20

Orlando (MCO)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2987

07:45

Midway, Chicago (MDW)

11:20

Orlando (MCO)

Effective 2025-06-05 through 2025-07-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2987

07:45

Midway, Chicago (MDW)

11:20

Orlando (MCO)

Effective 2025-07-07 through 2025-08-04

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2987

08:10

Midway, Chicago (MDW)

11:50

Orlando (MCO)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2987

09:15

Midway, Chicago (MDW)

12:50

Orlando (MCO)

Effective 2025-11-08 through 2025-11-15

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2987

09:15

Midway, Chicago (MDW)

12:50

Orlando (MCO)

Effective 2025-12-06 through 2025-12-13

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2987

10:40

Midway, Chicago (MDW)

14:15

Orlando (MCO)

Effective 2025-11-04 through 2025-11-12

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2987

10:40

Midway, Chicago (MDW)

14:15

Orlando (MCO)

Effective 2025-11-17 through 2025-11-20

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2987

10:40

Midway, Chicago (MDW)

14:15

Orlando (MCO)

Effective 2025-12-02 through 2025-12-11

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2987

10:40

Midway, Chicago (MDW)

14:15

Orlando (MCO)

Effective 2025-12-15 through 2025-12-17

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-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.

Return (MCO-MDW) flights

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