All airlines flying from Orlando (MCO) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Sat
08:05
Orlando (MCO)
09:55
Chicago Midway (MDW) Southwest Airlines WN 2835 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-06-06 through 2026-08-01 |
| Mon,Thu,Fri
08:15
Orlando (MCO)
10:00
Chicago Midway (MDW) Southwest Airlines WN 2835 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-06-04 through 2026-08-03 |
| Sun
09:10
Orlando (MCO)
11:00
Chicago Midway (MDW) Southwest Airlines WN 2950 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-04-12 through 2026-05-17 |
| Sun
09:10
Orlando (MCO)
11:00
Chicago Midway (MDW) Southwest Airlines WN 2950 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-05-31 |
| Sat
09:10
Orlando (MCO)
11:00
Chicago Midway (MDW) Southwest Airlines WN 2972 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-03 |
| Mon,Tue,Fri,Sun
09:15
Orlando (MCO)
11:05
Chicago Midway (MDW) Southwest Airlines WN 2972 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-04 |
| Sun
17:20
Orlando (MCO)
19:10
Chicago Midway (MDW) Southwest Airlines WN 3089 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-04-12 through 2026-05-17 |
| Sun
17:20
Orlando (MCO)
19:10
Chicago Midway (MDW) Southwest Airlines WN 3089 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Operates only on 2026-05-31 |
| Sun
17:50
Orlando (MCO)
19:45
Chicago Midway (MDW) Southwest Airlines WN 3089 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Operates only on 2026-05-24 |
| Sun
07:05
Orlando (MCO)
09:00
Chicago Midway (MDW) Southwest Airlines WN 3142 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-04-12 through 2026-05-17 |
| Sun
07:05
Orlando (MCO)
09:00
Chicago Midway (MDW) Southwest Airlines WN 3142 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Operates only on 2026-05-31 |
| Tue,Wed
07:15
Orlando (MCO)
09:10
Chicago Midway (MDW) Southwest Airlines WN 3142 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-04-07 through 2026-06-03 |
| Mon,Thu,Fri
07:20
Orlando (MCO)
09:15
Chicago Midway (MDW) Southwest Airlines WN 3142 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-04-09 through 2026-06-01 |
| Sat
07:20
Orlando (MCO)
09:15
Chicago Midway (MDW) Southwest Airlines WN 3142 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-04-11 through 2026-05-30 |
| Sun
07:55
Orlando (MCO)
09:50
Chicago Midway (MDW) Southwest Airlines WN 3142 Non-stop Boeing 737-800 (73H) 2:55 Operates only on 2026-05-24 |
| Mon,Thu,Fri
11:40
Orlando (MCO)
13:30
Chicago Midway (MDW) Southwest Airlines WN 3144 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-04-09 through 2026-06-01 |
| Mon,Thu,Fri
19:15
Orlando (MCO)
21:10
Chicago Midway (MDW) Southwest Airlines WN 3155 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-03-05 through 2026-04-06 |
| Sat
19:55
Orlando (MCO)
21:55
Chicago Midway (MDW) Southwest Airlines WN 3155 Non-stop Boeing 737-800 (73H) 3:00 Effective 2026-03-07 through 2026-04-04 |
| Sun
20:00
Orlando (MCO)
22:00
Chicago Midway (MDW) Southwest Airlines WN 3155 Non-stop Boeing 737-800 (73H) 3:00 Effective 2026-03-08 through 2026-04-05 |
| Tue,Wed
20:40
Orlando (MCO)
22:40
Chicago Midway (MDW) Southwest Airlines WN 3155 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-03-10 through 2026-04-01 |
| Mon
17:05
Orlando (MCO)
18:55
Chicago Midway (MDW) Southwest Airlines WN 3221 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Operates only on 2026-01-05 |
| Wed,Thu
18:50
Orlando (MCO)
20:40
Chicago Midway (MDW) Southwest Airlines WN 3221 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-01 |
| Sat
15:15
Orlando (MCO)
17:05
Chicago Midway (MDW) Southwest Airlines WN 3269 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-04-11 through 2026-05-30 |
| Tue,Wed
15:40
Orlando (MCO)
17:30
Chicago Midway (MDW) Southwest Airlines WN 3269 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-04-07 through 2026-06-03 |
| Sun
15:55
Orlando (MCO)
17:45
Chicago Midway (MDW) Southwest Airlines WN 3269 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-04-12 through 2026-05-17 |
| Sun
15:55
Orlando (MCO)
17:45
Chicago Midway (MDW) Southwest Airlines WN 3269 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-05-31 |
| Sun
12:15
Orlando (MCO)
14:10
Chicago Midway (MDW) Southwest Airlines WN 3291 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-08 through 2026-04-05 |
| Sat
21:40
Orlando (MCO)
23:25
Chicago Midway (MDW) Southwest Airlines WN 3328 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Operates only on 2026-01-03 |
| Mon,Tue,Fri,Sun
22:40
Orlando (MCO)
00:25
Chicago Midway (MDW) Southwest Airlines WN 3328 Non-stop Boeing 737-800 (73H) 2:45 Valid until 2026-01-04 The flight arrives 1 day after departure. |
| Sun
16:55
Orlando (MCO)
18:55
Chicago Midway (MDW) Southwest Airlines WN 3587 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-03-08 through 2026-04-05 |
| Mon,Tue,Fri,Sun
12:35
Orlando (MCO)
14:25
Chicago Midway (MDW) Southwest Airlines WN 3602 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-04 |
| Tue,Wed
11:55
Orlando (MCO)
13:45
Chicago Midway (MDW) Southwest Airlines WN 3783 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-04-07 through 2026-06-03 |
| Fri
07:05
Orlando (MCO)
09:09
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:04 Operates only on 2026-01-16 |
| Mon
07:08
Orlando (MCO)
09:12
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:04 Operates only on 2026-01-19 |
| Thu
08:30
Orlando (MCO)
10:32
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:02 Operates only on 2026-01-15 |
| Thu,Sun
10:15
Orlando (MCO)
12:19
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:04 Effective 2026-03-26 through 2026-03-29 |
| Mon,Fri,Sat
11:05
Orlando (MCO)
13:08
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:03 Effective 2026-03-06 through 2026-03-23 |
| Sat
11:05
Orlando (MCO)
13:08
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:03 Operates only on 2026-03-28 |
| Mon,Fri
12:05
Orlando (MCO)
14:11
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:06 Effective 2026-03-27 through 2026-03-30 |
| Thu,Fri,Sun
12:20
Orlando (MCO)
14:26
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:06 Effective 2026-02-12 through 2026-03-05 |
| Sat
12:49
Orlando (MCO)
14:55
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:06 Effective 2026-02-14 through 2026-02-28 |
| Tue
13:31
Orlando (MCO)
15:33
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:02 Effective 2026-03-24 through 2026-03-31 |
| Sun
15:01
Orlando (MCO)
17:05
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:04 Operates only on 2026-01-18 |
| Sun
15:40
Orlando (MCO)
17:44
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:04 Effective 2026-03-08 through 2026-03-22 |
| Fri
17:49
Orlando (MCO)
19:52
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:03 Effective 2026-01-23 through 2026-02-06 |
| Sun
17:49
Orlando (MCO)
19:52
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:03 Operates only on 2026-02-08 |
| Mon
17:55
Orlando (MCO)
19:58
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:03 Effective 2026-01-26 through 2026-02-09 |
| Mon
18:27
Orlando (MCO)
20:32
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:05 Effective 2026-02-16 through 2026-03-02 |
| Sat
18:56
Orlando (MCO)
20:53
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 2:57 Operates only on 2026-01-03 |
| Mon,Thu-Sun
19:58
Orlando (MCO)
21:58
Chicago Midway (MDW) Frontier Airlines F9 3853 Non-stop Airbus A320neo (32N) 3:00 Effective 2026-04-02 through 2026-04-13 |
- A domestic route departing from the Orlando airport (MCO) and arriving at Chicago Midway 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 3:08.
