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

FLIGHT SCHEDULE
Direct Flights:
Sat 20:50 Midway, Chicago (MDW) 00:25 Orlando (MCO) Southwest Airlines WN 4658 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-12-20 through 2026-01-03 The flight arrives 1 day after departure.
Sat 15:20 Midway, Chicago (MDW) 18:55 Orlando (MCO) Southwest Airlines WN 4678 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2025-11-22 through 2025-11-29
Sat 15:20 Midway, Chicago (MDW) 18:55 Orlando (MCO) Southwest Airlines WN 4678 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2025-12-20 through 2026-01-03
Sun 19:50 Midway, Chicago (MDW) 23:20 Orlando (MCO) Southwest Airlines WN 4710 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2025-10-05 through 2025-10-26
Tue,Wed 13:00 Midway, Chicago (MDW) 16:40 Orlando (MCO) Southwest Airlines WN 4752 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 17:15 Midway, Chicago (MDW) 21:00 Orlando (MCO) Southwest Airlines WN 4752 Non-stop Boeing 737-800 (73H) 2:45 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 17:15 Midway, Chicago (MDW) 21:00 Orlando (MCO) Southwest Airlines WN 4752 Non-stop Boeing 737-800 (73H) 2:45 Effective 2025-07-07 through 2025-08-04
Fri 17:30 Midway, Chicago (MDW) 21:15 Orlando (MCO) Southwest Airlines WN 4752 Non-stop Boeing 737-800 (73H) 2:45 Operates only on 2025-07-04
Sat 17:45 Midway, Chicago (MDW) 21:30 Orlando (MCO) Southwest Airlines WN 4752 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2025-06-07 through 2025-08-02
Sun 21:20 Midway, Chicago (MDW) 01:00 Orlando (MCO) Southwest Airlines WN 4752 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2025-06-08 through 2025-08-03 The flight arrives 1 day after departure.
Mon,Thu,Fri 05:00 Midway, Chicago (MDW) 08:30 Orlando (MCO) Southwest Airlines WN 4831 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2025-06-05 through 2025-07-03
Tue,Wed 05:00 Midway, Chicago (MDW) 08:30 Orlando (MCO) Southwest Airlines WN 4831 Non-stop Boeing 737-800 (73H) 2:30 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 05:00 Midway, Chicago (MDW) 08:30 Orlando (MCO) Southwest Airlines WN 4831 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2025-07-07 through 2025-08-04
Sun 05:05 Midway, Chicago (MDW) 08:35 Orlando (MCO) Southwest Airlines WN 4831 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2025-06-08 through 2025-08-03
Sat 05:25 Midway, Chicago (MDW) 09:00 Orlando (MCO) Southwest Airlines WN 4831 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-06-07 through 2025-08-02
Fri 06:30 Midway, Chicago (MDW) 10:05 Orlando (MCO) Southwest Airlines WN 4831 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Operates only on 2025-07-04
Sat 09:15 Midway, Chicago (MDW) 12:50 Orlando (MCO) Southwest Airlines WN 4841 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-11-22 through 2025-11-29
Sat 09:15 Midway, Chicago (MDW) 12:50 Orlando (MCO) Southwest Airlines WN 4841 Non-stop Boeing 737-800 (73H) 2:35 Effective 2025-12-20 through 2026-01-03
Mon-Wed 09:30 Midway, Chicago (MDW) 13:10 Orlando (MCO) Southwest Airlines WN 4841 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 09:30 Midway, Chicago (MDW) 13:10 Orlando (MCO) Southwest Airlines WN 4841 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2025-12-19 through 2026-01-04
Mon 11:00 Midway, Chicago (MDW) 14:35 Orlando (MCO) Southwest Airlines WN 6320 Non-stop Boeing 737-700 (73W) 2:35 Operates only on 2025-05-12
Thu,Fri 11:00 Midway, Chicago (MDW) 14:35 Orlando (MCO) Southwest Airlines WN 6342 Non-stop Boeing 737-700 (73W) 2:35 Effective 2025-05-08 through 2025-05-09
Thu 15:05 Midway, Chicago (MDW) 18:55 Orlando (MCO) Southwest Airlines WN 6433 Non-stop Boeing 737-700 (73W) 2:50 Operates only on 2025-06-05
Sun 11:00 Midway, Chicago (MDW) 14:35 Orlando (MCO) Southwest Airlines WN 6550 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-05-04 through 2025-05-18
Sun 11:00 Midway, Chicago (MDW) 14:35 Orlando (MCO) Southwest Airlines WN 6550 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Operates only on 2025-06-01
Sat 10:00 Midway, Chicago (MDW) 13:40 Orlando (MCO) Southwest Airlines WN 6555 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2025-05-03 through 2025-05-31
Non-Direct Flights:
Tue,Wed 08:30 Midway, Chicago (MDW) 13:55 Orlando (MCO) Southwest Airlines WN 236 1-stop Boeing 737-800 (73H) 4:25 Valid until 2025-06-04
Sun 09:10 Midway, Chicago (MDW) 14:30 Orlando (MCO) Southwest Airlines WN 247 1-stop Boeing 737-700 (73W) 4:20 Effective 2025-06-08 through 2025-08-03
Sun 10:10 Midway, Chicago (MDW) 15:55 Orlando (MCO) Southwest Airlines WN 257 1-stop Boeing 737-700 (73W) 4:45 Effective 2025-06-08 through 2025-08-03
Tue,Wed 13:00 Midway, Chicago (MDW) 20:00 Orlando (MCO) Southwest Airlines WN 258 1-stop Boeing 737 MAX 8 (7M8) 6:00 Valid until 2025-06-04
Mon,Thu,Fri,Sun 13:25 Midway, Chicago (MDW) 20:00 Orlando (MCO) Southwest Airlines WN 267 1-stop Boeing 737 MAX 8 (7M8) 5:35 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 13:25 Midway, Chicago (MDW) 20:00 Orlando (MCO) Southwest Airlines WN 267 1-stop Boeing 737 MAX 8 (7M8) 5:35 Effective 2025-11-21 through 2025-11-28
Fri,Sun 13:25 Midway, Chicago (MDW) 20:00 Orlando (MCO) Southwest Airlines WN 267 1-stop Boeing 737 MAX 8 (7M8) 5:35 Effective 2025-12-07 through 2025-12-14
Thu 13:25 Midway, Chicago (MDW) 20:00 Orlando (MCO) Southwest Airlines WN 267 1-stop Boeing 737 MAX 8 (7M8) 5:35 Operates only on 2025-12-18
Mon 13:25 Midway, Chicago (MDW) 20:00 Orlando (MCO) Southwest Airlines WN 267 1-stop Boeing 737 MAX 8 (7M8) 5:35 Operates only on 2026-01-05
Mon,Thu,Fri,Sun 09:55 Midway, Chicago (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 419 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 09:55 Midway, Chicago (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 419 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2025-11-21 through 2025-11-28
Fri,Sun 09:55 Midway, Chicago (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 419 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2025-12-07 through 2025-12-14
Thu 09:55 Midway, Chicago (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 419 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Operates only on 2025-12-18
Mon 09:55 Midway, Chicago (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 419 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Operates only on 2026-01-05
Sun 13:00 Midway, Chicago (MDW) 19:10 Orlando (MCO) Southwest Airlines WN 436 1-stop Boeing 737-700 (73W) 5:10 Operates only on 2025-05-25
Sun 14:55 Midway, Chicago (MDW) 21:10 Orlando (MCO) Southwest Airlines WN 436 1-stop Boeing 737 MAX 8 (7M8) 5:15 Valid until 2025-05-18
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

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 2:50.

Feedback - Disclaimer - Privacy

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN4658

20:50

Midway, Chicago (MDW)

00:25(+1)

Orlando (MCO)

Effective 2025-12-20 through 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Southwest Airlines WN4678

15:20

Midway, Chicago (MDW)

18:55

Orlando (MCO)

Effective 2025-11-22 through 2025-11-29

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN4678

15:20

Midway, Chicago (MDW)

18:55

Orlando (MCO)

Effective 2025-12-20 through 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN4710

19:50

Midway, Chicago (MDW)

23:20

Orlando (MCO)

Effective 2025-10-05 through 2025-10-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4752

13:00

Midway, Chicago (MDW)

16:40

Orlando (MCO)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN4752

17:15

Midway, Chicago (MDW)

21:00

Orlando (MCO)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN4752

17:15

Midway, Chicago (MDW)

21:00

Orlando (MCO)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN4752

17:30

Midway, Chicago (MDW)

21:15

Orlando (MCO)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN4752

17:45

Midway, Chicago (MDW)

21:30

Orlando (MCO)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN4752

21:20

Midway, Chicago (MDW)

01:00(+1)

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)
The flight arrives 1 day after departure.

Southwest Airlines WN4831

05:00

Midway, Chicago (MDW)

08:30

Orlando (MCO)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4831

05:00

Midway, Chicago (MDW)

08:30

Orlando (MCO)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:30, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN4831

05:00

Midway, Chicago (MDW)

08:30

Orlando (MCO)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4831

05:05

Midway, Chicago (MDW)

08:35

Orlando (MCO)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4831

05:25

Midway, Chicago (MDW)

09:00

Orlando (MCO)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN4831

06:30

Midway, Chicago (MDW)

10:05

Orlando (MCO)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

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

Southwest Airlines WN4841

09:15

Midway, Chicago (MDW)

12:50

Orlando (MCO)

Effective 2025-11-22 through 2025-11-29

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN4841

09:15

Midway, Chicago (MDW)

12:50

Orlando (MCO)

Effective 2025-12-20 through 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN4841

09:30

Midway, Chicago (MDW)

13:10

Orlando (MCO)

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN4841

09:30

Midway, Chicago (MDW)

13:10

Orlando (MCO)

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

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN6320

11:00

Midway, Chicago (MDW)

14:35

Orlando (MCO)

Operates only on 2025-05-12

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN6342

11:00

Midway, Chicago (MDW)

14:35

Orlando (MCO)

Effective 2025-05-08 through 2025-05-09

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN6433

15:05

Midway, Chicago (MDW)

18:55

Orlando (MCO)

Operates only on 2025-06-05

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:50, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN6550

11:00

Midway, Chicago (MDW)

14:35

Orlando (MCO)

Effective 2025-05-04 through 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN6550

11:00

Midway, Chicago (MDW)

14:35

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)

Southwest Airlines WN6555

10:00

Midway, Chicago (MDW)

13:40

Orlando (MCO)

Effective 2025-05-03 through 2025-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN236

08:30

Midway, Chicago (MDW)

13:55

Orlando (MCO)

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:25, 1-stop
Boeing 737-800 (73H)

Southwest Airlines WN247

09:10

Midway, Chicago (MDW)

14:30

Orlando (MCO)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:20, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN257

10:10

Midway, Chicago (MDW)

15:55

Orlando (MCO)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:45, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN258

13:00

Midway, Chicago (MDW)

20:00

Orlando (MCO)

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:00, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN267

13:25

Midway, Chicago (MDW)

20:00

Orlando (MCO)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 5:35, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN267

13:25

Midway, Chicago (MDW)

20:00

Orlando (MCO)

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

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 5:35, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN267

13:25

Midway, Chicago (MDW)

20:00

Orlando (MCO)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 5:35, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN267

13:25

Midway, Chicago (MDW)

20:00

Orlando (MCO)

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 5:35, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN267

13:25

Midway, Chicago (MDW)

20:00

Orlando (MCO)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:35, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN419

09:55

Midway, Chicago (MDW)

14:55

Orlando (MCO)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN419

09:55

Midway, Chicago (MDW)

14:55

Orlando (MCO)

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

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN419

09:55

Midway, Chicago (MDW)

14:55

Orlando (MCO)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN419

09:55

Midway, Chicago (MDW)

14:55

Orlando (MCO)

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN419

09:55

Midway, Chicago (MDW)

14:55

Orlando (MCO)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN436

13:00

Midway, Chicago (MDW)

19:10

Orlando (MCO)

Operates only on 2025-05-25

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN436

14:55

Midway, Chicago (MDW)

21:10

Orlando (MCO)

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:15, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN436

14:55

Midway, Chicago (MDW)

21:10

Orlando (MCO)

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:15, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN546

08:05

Midway, Chicago (MDW)

13:55

Orlando (MCO)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN546

08:05

Midway, Chicago (MDW)

13:55

Orlando (MCO)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN644

17:50

Midway, Chicago (MDW)

22:55

Orlando (MCO)

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)

Southwest Airlines WN967

07:55

Midway, Chicago (MDW)

12:45

Orlando (MCO)

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)

Southwest Airlines WN990

07:20

Midway, Chicago (MDW)

13:05

Orlando (MCO)

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)

Southwest Airlines WN996

10:45

Midway, Chicago (MDW)

16:25

Orlando (MCO)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:40, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN1073

09:05

Midway, Chicago (MDW)

14:10

Orlando (MCO)

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)

prev Page 6 / 9 next

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.

All MDW-MCO flights

All Southwest Airlines flights

Return (MCO-MDW) flights

Feedback - Disclaimer - Privacy