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

FLIGHT SCHEDULE
Non-Direct Flights:
Mon,Thu,Fri 13:20 Chicago Midway (MDW) 19:35 Orlando (MCO) Southwest Airlines WN 2877 1-stop Boeing 737 MAX 8 (7M8) 5:15 Effective 2026-06-04 through 2026-08-03
Sat 10:25 Chicago Midway (MDW) 16:00 Orlando (MCO) Southwest Airlines WN 2915 1-stop Boeing 737-700 (Scimitar Winglets) 4:35 Effective 2026-02-14 through 2026-02-28
Wed,Thu 14:25 Chicago Midway (MDW) 19:15 Orlando (MCO) Southwest Airlines WN 3027 1-stop Boeing 737-700 (73W) 3:50 Valid until 2026-01-01
Mon,Thu,Fri 07:40 Chicago Midway (MDW) 12:55 Orlando (MCO) Southwest Airlines WN 3108 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Effective 2026-04-09 through 2026-06-01
Sat 07:55 Chicago Midway (MDW) 14:10 Orlando (MCO) Southwest Airlines WN 3222 1-stop Boeing 737 MAX 8 (7M8) 5:15 Effective 2026-06-06 through 2026-08-01
Tue,Wed 09:10 Chicago Midway (MDW) 15:15 Orlando (MCO) Southwest Airlines WN 3222 1-stop Boeing 737-700 (Scimitar Winglets) 5:05 Effective 2026-06-09 through 2026-07-29
Sat 10:20 Chicago Midway (MDW) 15:15 Orlando (MCO) Southwest Airlines WN 3271 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-06-06 through 2026-08-01
Sun 13:15 Chicago Midway (MDW) 19:20 Orlando (MCO) Southwest Airlines WN 3304 1-stop Boeing 737-800 (73H) 5:05 Effective 2026-03-08 through 2026-04-05
Sat 07:40 Chicago Midway (MDW) 13:50 Orlando (MCO) Southwest Airlines WN 3336 1-stop Boeing 737 MAX 8 (7M8) 5:10 Effective 2026-04-11 through 2026-05-30
Sat 12:45 Chicago Midway (MDW) 17:55 Orlando (MCO) Southwest Airlines WN 3396 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-04-11 through 2026-05-30
Sun 11:55 Chicago Midway (MDW) 17:30 Orlando (MCO) Southwest Airlines WN 3579 1-stop Boeing 737-700 (Scimitar Winglets) 4:35 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 12:40 Chicago Midway (MDW) 18:15 Orlando (MCO) Southwest Airlines WN 3579 1-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-06-04 through 2026-08-03
Mon,Tue,Fri,Sun 09:45 Chicago Midway (MDW) 15:40 Orlando (MCO) Southwest Airlines WN 3592 1-stop Boeing 737 MAX 8 (7M8) 4:55 Valid until 2026-01-04
Mon 13:25 Chicago Midway (MDW) 18:40 Orlando (MCO) Southwest Airlines WN 3611 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Operates only on 2026-01-05
Sat 11:00 Chicago Midway (MDW) 16:20 Orlando (MCO) Southwest Airlines WN 3702 1-stop Boeing 737 MAX 8 (7M8) 4:20 Valid until 2026-01-03
Wed,Thu 13:25 Chicago Midway (MDW) 18:50 Orlando (MCO) Southwest Airlines WN 3707 1-stop Boeing 737 MAX 8 (7M8) 4:25 Valid until 2026-01-01
Sat 07:40 Chicago Midway (MDW) 12:30 Orlando (MCO) Southwest Airlines WN 3787 1-stop Boeing 737-800 (73H) 3:50 Effective 2026-04-11 through 2026-05-30
Mon 09:10 Chicago Midway (MDW) 14:25 Orlando (MCO) Southwest Airlines WN 3788 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Operates only on 2026-01-05
Sat 07:45 Chicago Midway (MDW) 13:55 Orlando (MCO) Southwest Airlines WN 3978 1-stop Boeing 737-800 (73H) 5:10 Effective 2026-03-07 through 2026-04-04
Sun 18:45 Chicago Midway (MDW) 23:45 Orlando (MCO) Southwest Airlines WN 4043 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-06-07 through 2026-08-02
Sun 07:35 Chicago Midway (MDW) 13:05 Orlando (MCO) Southwest Airlines WN 4086 1-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-03-08 through 2026-04-05
Sun 07:45 Chicago Midway (MDW) 14:00 Orlando (MCO) Southwest Airlines WN 4122 1-stop Boeing 737-700 (Scimitar Winglets) 5:15 Effective 2026-06-07 through 2026-08-02
Mon,Tue,Fri,Sun 09:30 Chicago Midway (MDW) 15:25 Orlando (MCO) Southwest Airlines WN 4498 1-stop Boeing 737 MAX 8 (7M8) 4:55 Valid until 2026-01-05
Sat 11:00 Chicago Midway (MDW) 16:25 Orlando (MCO) Southwest Airlines WN 4506 1-stop Boeing 737 MAX 8 (7M8) 4:25 Valid until 2026-01-03
Sat 12:45 Chicago Midway (MDW) 18:00 Orlando (MCO) Southwest Airlines WN 4601 1-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-03-07 through 2026-04-04
Mon,Thu 09:30 Chicago Midway (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 4972 1-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 09:30 Chicago Midway (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 4972 1-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-02-20 through 2026-03-01
Fri 09:40 Chicago Midway (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 4972 1-stop Boeing 737 MAX 8 (7M8) 4:15 Operates only on 2026-02-13
Thu,Fri,Sun 09:45 Chicago Midway (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 4972 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-01-11 through 2026-01-16
Mon,Sun 09:45 Chicago Midway (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 4972 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-01-19 through 2026-01-25
Fri,Sun 09:45 Chicago Midway (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 4972 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-02-01 through 2026-02-06
Thu 09:45 Chicago Midway (MDW) 15:00 Orlando (MCO) Southwest Airlines WN 4972 1-stop Boeing 737 MAX 8 (7M8) 4:15 Operates only on 2026-02-05
Mon,Sun 09:45 Chicago Midway (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 4972 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 09:45 Chicago Midway (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 4972 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-02-17 through 2026-02-23
Mon 09:45 Chicago Midway (MDW) 14:55 Orlando (MCO) Southwest Airlines WN 4972 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Operates only on 2026-03-02
Mon,Thu,Fri 09:40 Chicago Midway (MDW) 15:25 Orlando (MCO) Southwest Airlines WN 4994 1-stop Boeing 737-700 (Scimitar Winglets) 4:45 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 09:40 Chicago Midway (MDW) 15:25 Orlando (MCO) Southwest Airlines WN 4994 1-stop Boeing 737-700 (Scimitar Winglets) 4:45 Effective 2026-02-20 through 2026-03-01
Mon,Thu,Fri 11:15 Chicago Midway (MDW) 20:55 Orlando (MCO) Southwest Airlines WN 155 2-stop Boeing 737-700 (Scimitar Winglets) 8:40 Effective 2026-04-09 through 2026-06-01
Mon,Thu,Fri 10:25 Chicago Midway (MDW) 18:35 Orlando (MCO) Southwest Airlines WN 2529 2-stop Boeing 737-700 (Scimitar Winglets) 7:10 Effective 2026-06-04 through 2026-08-03
Tue,Wed 09:10 Chicago Midway (MDW) 19:00 Orlando (MCO) Southwest Airlines WN 1266 3-stop Boeing 737 MAX 8 (7M8) 8:50 Effective 2026-04-07 through 2026-06-03
Thu,Fri,Sun 09:55 Chicago Midway (MDW) 20:30 Orlando (MCO) Southwest Airlines WN 4888 3-stop Boeing 737-700 (Scimitar Winglets) 9:35 Effective 2026-01-11 through 2026-01-16
Mon,Sun 09:55 Chicago Midway (MDW) 20:30 Orlando (MCO) Southwest Airlines WN 4888 3-stop Boeing 737-700 (Scimitar Winglets) 9:35 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 09:55 Chicago Midway (MDW) 20:30 Orlando (MCO) Southwest Airlines WN 4888 3-stop Boeing 737-700 (Scimitar Winglets) 9:35 Effective 2026-02-01 through 2026-02-06
Mon,Sun 09:55 Chicago Midway (MDW) 20:30 Orlando (MCO) Southwest Airlines WN 4888 3-stop Boeing 737-700 (Scimitar Winglets) 9:35 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 09:55 Chicago Midway (MDW) 20:30 Orlando (MCO) Southwest Airlines WN 4888 3-stop Boeing 737-700 (Scimitar Winglets) 9:35 Effective 2026-02-17 through 2026-02-23
Mon 09:55 Chicago Midway (MDW) 20:30 Orlando (MCO) Southwest Airlines WN 4888 3-stop Boeing 737-700 (Scimitar Winglets) 9:35 Operates only on 2026-03-02
Direct Codeshare Flights:
Mon,Fri,Sat 06:15 Chicago Midway (MDW) 10:05 Orlando (MCO) Volaris Y4 2170 Non-stop Airbus A320 (320) 2:50 Effective 2026-03-06 through 2026-03-23 Codeshare flight, operated by Frontier Airlines.(F9)
Sat 06:15 Chicago Midway (MDW) 10:05 Orlando (MCO) Volaris Y4 2170 Non-stop Airbus A320 (320) 2:50 Operates only on 2026-03-28 Codeshare flight, operated by Frontier Airlines.(F9)
Mon,Fri 07:15 Chicago Midway (MDW) 11:05 Orlando (MCO) Volaris Y4 2170 Non-stop Airbus A320 (320) 2:50 Effective 2026-03-27 through 2026-03-30 Codeshare flight, operated by Frontier Airlines.(F9)
Thu,Fri,Sun 07:30 Chicago Midway (MDW) 11:20 Orlando (MCO) Volaris Y4 2170 Non-stop Airbus A320 (320) 2:50 Effective 2026-02-12 through 2026-03-05 Codeshare flight, operated by Frontier Airlines.(F9)

1 2 3 ... 5 6 7 8 9

A domestic route departing from the Chicago Midway 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.

Return (MCO-MDW) flights

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

FLIGHT SCHEDULE

Non-Direct Flights:

Southwest Airlines WN2877

13:20

Chicago Midway (MDW)

19:35

Orlando (MCO)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN2915

10:25

Chicago Midway (MDW)

16:00

Orlando (MCO)

Effective 2026-02-14 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:35, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3027

14:25

Chicago Midway (MDW)

19:15

Orlando (MCO)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:50, 1-stop
Boeing 737-700 (73W)

Non-Direct Flights:

Southwest Airlines WN3108

07:40

Chicago Midway (MDW)

12:55

Orlando (MCO)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3222

07:55

Chicago Midway (MDW)

14:10

Orlando (MCO)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN3222

09:10

Chicago Midway (MDW)

15:15

Orlando (MCO)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3271

10:20

Chicago Midway (MDW)

15:15

Orlando (MCO)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3304

13:15

Chicago Midway (MDW)

19:20

Orlando (MCO)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:05, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN3336

07:40

Chicago Midway (MDW)

13:50

Orlando (MCO)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:10, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3396

12:45

Chicago Midway (MDW)

17:55

Orlando (MCO)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3579

11:55

Chicago Midway (MDW)

17:30

Orlando (MCO)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3579

12:40

Chicago Midway (MDW)

18:15

Orlando (MCO)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:35, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3592

09:45

Chicago Midway (MDW)

15:40

Orlando (MCO)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:55, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3611

13:25

Chicago Midway (MDW)

18:40

Orlando (MCO)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3702

11:00

Chicago Midway (MDW)

16:20

Orlando (MCO)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:20, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3707

13:25

Chicago Midway (MDW)

18:50

Orlando (MCO)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3787

07:40

Chicago Midway (MDW)

12:30

Orlando (MCO)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:50, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN3788

09:10

Chicago Midway (MDW)

14:25

Orlando (MCO)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3978

07:45

Chicago Midway (MDW)

13:55

Orlando (MCO)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:10, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN4043

18:45

Chicago Midway (MDW)

23:45

Orlando (MCO)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN4086

07:35

Chicago Midway (MDW)

13:05

Orlando (MCO)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:30, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4122

07:45

Chicago Midway (MDW)

14:00

Orlando (MCO)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4498

09:30

Chicago Midway (MDW)

15:25

Orlando (MCO)

Valid until 2026-01-05

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:55, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4506

11:00

Chicago Midway (MDW)

16:25

Orlando (MCO)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4601

12:45

Chicago Midway (MDW)

18:00

Orlando (MCO)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4972

09:30

Chicago Midway (MDW)

14:55

Orlando (MCO)

Effective 2026-02-12 through 2026-02-16

Mon

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4972

09:30

Chicago Midway (MDW)

14:55

Orlando (MCO)

Effective 2026-02-20 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4972

09:40

Chicago Midway (MDW)

14:55

Orlando (MCO)

Operates only on 2026-02-13

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 4:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4972

09:45

Chicago Midway (MDW)

14:55

Orlando (MCO)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4972

09:45

Chicago Midway (MDW)

14:55

Orlando (MCO)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4972

09:45

Chicago Midway (MDW)

14:55

Orlando (MCO)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4972

09:45

Chicago Midway (MDW)

15:00

Orlando (MCO)

Operates only on 2026-02-05

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4972

09:45

Chicago Midway (MDW)

14:55

Orlando (MCO)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4972

09:45

Chicago Midway (MDW)

14:55

Orlando (MCO)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4972

09:45

Chicago Midway (MDW)

14:55

Orlando (MCO)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4994

09:40

Chicago Midway (MDW)

15:25

Orlando (MCO)

Effective 2026-02-12 through 2026-02-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4994

09:40

Chicago Midway (MDW)

15:25

Orlando (MCO)

Effective 2026-02-20 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN155

11:15

Chicago Midway (MDW)

20:55

Orlando (MCO)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 8:40, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2529

10:25

Chicago Midway (MDW)

18:35

Orlando (MCO)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 7:10, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1266

09:10

Chicago Midway (MDW)

19:00

Orlando (MCO)

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 8:50, 3-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4888

09:55

Chicago Midway (MDW)

20:30

Orlando (MCO)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 9:35, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4888

09:55

Chicago Midway (MDW)

20:30

Orlando (MCO)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 9:35, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4888

09:55

Chicago Midway (MDW)

20:30

Orlando (MCO)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 9:35, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4888

09:55

Chicago Midway (MDW)

20:30

Orlando (MCO)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 9:35, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4888

09:55

Chicago Midway (MDW)

20:30

Orlando (MCO)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 9:35, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4888

09:55

Chicago Midway (MDW)

20:30

Orlando (MCO)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 9:35, 3-stop
Boeing 737-700 (Scimitar Winglets)

Direct Codeshare Flights:

Volaris Y42170

06:15

Chicago Midway (MDW)

10:05

Orlando (MCO)

Effective 2026-03-06 through 2026-03-23

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat

Sun
-

Codeshare flight, operated by Frontier Airlines.(F9)

Duration: 2:50, non-stop
Airbus A320 (320)

Direct Codeshare Flights:

Volaris Y42170

06:15

Chicago Midway (MDW)

10:05

Orlando (MCO)

Operates only on 2026-03-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Codeshare flight, operated by Frontier Airlines.(F9)

Duration: 2:50, non-stop
Airbus A320 (320)

Direct Codeshare Flights:

Volaris Y42170

07:15

Chicago Midway (MDW)

11:05

Orlando (MCO)

Effective 2026-03-27 through 2026-03-30

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Codeshare flight, operated by Frontier Airlines.(F9)

Duration: 2:50, non-stop
Airbus A320 (320)

Direct Codeshare Flights:

Volaris Y42170

07:30

Chicago Midway (MDW)

11:20

Orlando (MCO)

Effective 2026-02-12 through 2026-03-05

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Codeshare flight, operated by Frontier Airlines.(F9)

Duration: 2:50, non-stop
Airbus A320 (320)

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A domestic route departing from the Chicago Midway 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.

Return (MCO-MDW) flights

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