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

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Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 20:20 Orlando (MCO) 22:10 Midway, Chicago (MDW)
Southwest Airlines WN 3726 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 20:20 Orlando (MCO) 22:10 Midway, Chicago (MDW)
Southwest Airlines WN 3726 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-07-07 through 2025-08-04
Tue,Wed 21:55 Orlando (MCO) 23:45 Midway, Chicago (MDW)
Southwest Airlines WN 3726 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 10:30 Orlando (MCO) 12:24 Midway, Chicago (MDW)
Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 2:54 Valid until 2025-05-19
Sun 15:33 Orlando (MCO) 17:30 Midway, Chicago (MDW)
Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 2:57 Effective 2025-05-04 through 2025-05-18
Sat 17:30 Orlando (MCO) 19:25 Midway, Chicago (MDW)
Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 2:55 Operates only on 2025-06-07
Mon,Thu,Fri,Sun 18:20 Orlando (MCO) 20:17 Midway, Chicago (MDW)
Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 2:57 Effective 2025-05-22 through 2025-05-30
Sat 18:20 Orlando (MCO) 20:17 Midway, Chicago (MDW)
Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 2:57 Operates only on 2025-05-31
Mon,Thu,Fri,Sun 18:22 Orlando (MCO) 20:17 Midway, Chicago (MDW)
Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 2:55 Effective 2025-06-01 through 2025-06-13
Mon,Thu-Sun 18:22 Orlando (MCO) 20:17 Midway, Chicago (MDW)
Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 2:55 Effective 2025-06-14 through 2025-07-04
Mon,Thu-Sun 18:22 Orlando (MCO) 20:21 Midway, Chicago (MDW)
Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 2:59 Effective 2025-07-05 through 2025-08-18
Sat 13:10 Orlando (MCO) 14:55 Midway, Chicago (MDW)
Southwest Airlines WN 3860 Non-stop Boeing 737-700 (Scimitar Winglets) 2:45 Effective 2025-10-04 through 2025-11-01
Sun 11:30 Orlando (MCO) 13:10 Midway, Chicago (MDW)
Southwest Airlines WN 3870 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2025-08-10 through 2025-08-24
Sun 11:30 Orlando (MCO) 13:10 Midway, Chicago (MDW)
Southwest Airlines WN 3870 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2025-09-07 through 2025-09-28
Tue,Wed 15:20 Orlando (MCO) 17:15 Midway, Chicago (MDW)
Southwest Airlines WN 4028 Non-stop Boeing 737-800 (73H) 2:55 Effective 2025-06-10 through 2025-07-30
Sun 17:25 Orlando (MCO) 19:15 Midway, Chicago (MDW)
Southwest Airlines WN 4382 Non-stop Boeing 737-700 (73W) 2:50 Operates only on 2025-05-25
Tue,Wed 07:30 Orlando (MCO) 09:20 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-11-04 through 2025-11-12
Mon-Thu 07:30 Orlando (MCO) 09:20 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-11-17 through 2025-11-20
Mon-Fri 07:30 Orlando (MCO) 09:20 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-12-02 through 2025-12-11
Mon-Wed 07:30 Orlando (MCO) 09:20 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-12-15 through 2025-12-17
Wed,Thu 07:30 Orlando (MCO) 09:20 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-12-24 through 2026-01-01
Mon,Thu,Fri,Sun 10:05 Orlando (MCO) 11:55 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 10:05 Orlando (MCO) 11:55 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-11-21 through 2025-11-28
Fri,Sun 10:05 Orlando (MCO) 11:55 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Effective 2025-12-07 through 2025-12-14
Thu 10:05 Orlando (MCO) 11:55 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2025-12-18
Mon 10:05 Orlando (MCO) 11:55 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2026-01-05
Sat 10:15 Orlando (MCO) 12:05 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2025-11-08 through 2025-11-15
Sat 10:15 Orlando (MCO) 12:05 Midway, Chicago (MDW)
Southwest Airlines WN 4535 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2025-12-06 through 2025-12-13
Mon,Thu,Fri 18:05 Orlando (MCO) 19:55 Midway, Chicago (MDW)
Southwest Airlines WN 4791 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2025-06-02
Sat 18:45 Orlando (MCO) 20:35 Midway, Chicago (MDW)
Southwest Airlines WN 4791 Non-stop Boeing 737-700 (73W) 2:50 Valid until 2025-05-31
Sun 07:15 Orlando (MCO) 09:05 Midway, Chicago (MDW)
Southwest Airlines WN 4859 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2025-05-25
Mon 11:05 Orlando (MCO) 12:55 Midway, Chicago (MDW)
Southwest Airlines WN 6200 Non-stop Boeing 737-700 (73W) 2:50 Operates only on 2025-05-05
Mon 15:20 Orlando (MCO) 17:10 Midway, Chicago (MDW)
Southwest Airlines WN 6321 Non-stop Boeing 737-700 (73W) 2:50 Operates only on 2025-05-12
Thu,Fri 15:20 Orlando (MCO) 17:10 Midway, Chicago (MDW)
Southwest Airlines WN 6343 Non-stop Boeing 737-700 (73W) 2:50 Effective 2025-05-08 through 2025-05-09
Sun 16:00 Orlando (MCO) 17:50 Midway, Chicago (MDW)
Southwest Airlines WN 6551 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2025-05-04 through 2025-05-18
Sun 16:00 Orlando (MCO) 17:50 Midway, Chicago (MDW)
Southwest Airlines WN 6551 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2025-06-01
Sat 14:45 Orlando (MCO) 16:35 Midway, Chicago (MDW)
Southwest Airlines WN 6556 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2025-05-03 through 2025-05-31
Non-Direct Flights:
Sat 15:40 Orlando (MCO) 18:50 Midway, Chicago (MDW)
Southwest Airlines WN 123 1-stop Boeing 737-800 (73H) 4:10 Effective 2025-06-07 through 2025-08-02
Tue,Wed 14:45 Orlando (MCO) 19:15 Midway, Chicago (MDW)
Southwest Airlines WN 301 1-stop Boeing 737-700 (Scimitar Winglets) 5:30 Effective 2025-10-07 through 2025-10-29
Mon,Thu,Fri 08:00 Orlando (MCO) 12:40 Midway, Chicago (MDW)
Southwest Airlines WN 364 1-stop Boeing 737 MAX 8 (7M8) 5:40 Effective 2025-10-02 through 2025-10-31
Mon,Thu,Fri 10:05 Orlando (MCO) 14:10 Midway, Chicago (MDW)
Southwest Airlines WN 367 1-stop Boeing 737 MAX 8 (7M8) 5:05 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 10:05 Orlando (MCO) 14:10 Midway, Chicago (MDW)
Southwest Airlines WN 367 1-stop Boeing 737 MAX 8 (7M8) 5:05 Effective 2025-07-07 through 2025-08-04
Sun 09:00 Orlando (MCO) 13:20 Midway, Chicago (MDW)
Southwest Airlines WN 418 1-stop Boeing 737-800 (73H) 5:20 Valid until 2025-05-18
Sun 09:00 Orlando (MCO) 13:20 Midway, Chicago (MDW)
Southwest Airlines WN 418 1-stop Boeing 737-800 (73H) 5:20 Operates only on 2025-06-01
Sat 13:45 Orlando (MCO) 18:35 Midway, Chicago (MDW)
Southwest Airlines WN 446 1-stop Boeing 737-800 (73H) 5:50 Effective 2025-10-04 through 2025-11-01
Tue,Wed 14:40 Orlando (MCO) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 460 1-stop Boeing 737-800 (73H) 5:50 Valid until 2025-06-04
Thu 09:10 Orlando (MCO) 12:15 Midway, Chicago (MDW)
Southwest Airlines WN 464 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Operates only on 2025-11-27
Sun 09:00 Orlando (MCO) 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 537 1-stop Boeing 737-700 (73W) 4:45 Effective 2025-06-08 through 2025-08-03
Fri 09:05 Orlando (MCO) 12:55 Midway, Chicago (MDW)
Southwest Airlines WN 537 1-stop Boeing 737-700 (73W) 4:50 Operates only on 2025-07-04
Sat 16:00 Orlando (MCO) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 659 1-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-11-22 through 2025-11-29
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All airlines flying from Orlando (MCO) to Midway, Chicago (MDW).
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Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Valid until 2025-05-19
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:54, non-stop
Airbus A320neo (32N)

Effective 2025-05-04 through 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:57, non-stop
Airbus A320neo (32N)

Operates only on 2025-06-07
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:55, non-stop
Airbus A320neo (32N)

Effective 2025-05-22 through 2025-05-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:57, non-stop
Airbus A320neo (32N)

Operates only on 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:57, non-stop
Airbus A320neo (32N)

Effective 2025-06-01 through 2025-06-13
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:55, non-stop
Airbus A320neo (32N)

Effective 2025-06-14 through 2025-07-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
Sun
Duration: 2:55, non-stop
Airbus A320neo (32N)

Effective 2025-07-05 through 2025-08-18
Mon
Tue
-
Wed
-
Thu
Fri
Sat
Sun
Duration: 2:59, non-stop
Airbus A320neo (32N)

Effective 2025-10-04 through 2025-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:55, non-stop
Boeing 737-800 (73H)

Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737-700 (73W)

Effective 2025-11-04 through 2025-11-12
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2025-11-17 through 2025-11-20
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2025-12-02 through 2025-12-11
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2025-12-15 through 2025-12-17
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2025-12-24 through 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-800 (73H)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:50, non-stop
Boeing 737-700 (73W)

Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-05-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-700 (73W)

Operates only on 2025-05-12
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-700 (73W)

Effective 2025-05-08 through 2025-05-09
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:50, non-stop
Boeing 737-700 (73W)

Effective 2025-05-04 through 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-05-03 through 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:50, non-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Effective 2025-06-07 through 2025-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:10, 1-stop
Boeing 737-800 (73H)

Effective 2025-10-07 through 2025-10-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-02 through 2025-10-31
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:40, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:05, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:05, 1-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:20, 1-stop
Boeing 737-800 (73H)

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:20, 1-stop
Boeing 737-800 (73H)

Effective 2025-10-04 through 2025-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:50, 1-stop
Boeing 737-800 (73H)

Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:50, 1-stop
Boeing 737-800 (73H)

Operates only on 2025-11-27
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:05, 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)

Operates only on 2025-07-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:30, 1-stop
Boeing 737 MAX 8 (7M8)
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  • A domestic route departing from the Orlando airport (MCO) and arriving at Midway, Chicago airport (MDW).
  • The flight distance is 990 miles, or 1593 km.
  • The timezone of the departure airport is UTC-5 , and the timezone of the arrival airport is UTC-6 . 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 2:40 and 3:05.