All airlines flying from Orlando (MCO) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Thu,Fri,Sun
06:50
Orlando (MCO)
08:45
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
06:50
Orlando (MCO)
08:45
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
06:50
Orlando (MCO)
08:45
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
06:50
Orlando (MCO)
08:45
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-02-09 through 2026-02-15 |
| Mon,Thu
06:50
Orlando (MCO)
08:45
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-12 through 2026-02-16 |
| Mon,Tue,Thu
06:50
Orlando (MCO)
08:45
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-02-17 through 2026-02-23 |
| Thu,Fri,Sun
06:50
Orlando (MCO)
08:45
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-20 through 2026-03-01 |
| Mon
06:50
Orlando (MCO)
08:45
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737-800 (73H) 2:55 Operates only on 2026-03-02 |
| Fri
06:55
Orlando (MCO)
08:50
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Operates only on 2026-02-13 |
| Sat
07:00
Orlando (MCO)
08:55
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-10 through 2026-02-07 |
| Sat
07:35
Orlando (MCO)
09:25
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-02-14 through 2026-02-21 |
| Sat
07:35
Orlando (MCO)
09:25
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-02-28 |
| Mon-Fri
09:25
Orlando (MCO)
11:15
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
09:25
Orlando (MCO)
11:15
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
09:25
Orlando (MCO)
11:15
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed,Sun
09:25
Orlando (MCO)
11:15
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
09:25
Orlando (MCO)
11:15
Chicago Midway (MDW) Southwest Airlines WN 2570 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-02-18 through 2026-03-04 |
| Mon,Thu,Fri
17:20
Orlando (MCO)
19:15
Chicago Midway (MDW) Southwest Airlines WN 2574 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
17:20
Orlando (MCO)
19:15
Chicago Midway (MDW) Southwest Airlines WN 2574 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-20 through 2026-03-01 |
| Sat
17:45
Orlando (MCO)
19:40
Chicago Midway (MDW) Southwest Airlines WN 2574 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-10 through 2026-01-31 |
| Sat
17:50
Orlando (MCO)
19:45
Chicago Midway (MDW) Southwest Airlines WN 2574 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-02-14 through 2026-02-28 |
| Sat
18:00
Orlando (MCO)
19:55
Chicago Midway (MDW) Southwest Airlines WN 2574 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Operates only on 2026-02-07 |
| Mon,Thu,Fri
09:40
Orlando (MCO)
11:25
Chicago Midway (MDW) Southwest Airlines WN 2610 Non-stop Boeing 737-700 (Scimitar Winglets) 2:45 Effective 2026-08-06 through 2026-09-28 |
| Tue,Wed
17:25
Orlando (MCO)
19:15
Chicago Midway (MDW) Southwest Airlines WN 2610 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-08-04 through 2026-09-30 |
| Sun
17:45
Orlando (MCO)
19:35
Chicago Midway (MDW) Southwest Airlines WN 2610 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-08-09 through 2026-09-27 |
| Sun
15:20
Orlando (MCO)
17:15
Chicago Midway (MDW) Southwest Airlines WN 2617 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-06-07 through 2026-08-02 |
| Sat
08:55
Orlando (MCO)
10:45
Chicago Midway (MDW) Southwest Airlines WN 2619 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-04-11 through 2026-05-30 |
| Mon,Thu,Fri
10:10
Orlando (MCO)
12:00
Chicago Midway (MDW) Southwest Airlines WN 2619 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-04-09 through 2026-06-01 |
| Tue,Wed
10:15
Orlando (MCO)
12:10
Chicago Midway (MDW) Southwest Airlines WN 2619 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-04-07 through 2026-06-03 |
| Sun
10:35
Orlando (MCO)
12:25
Chicago Midway (MDW) Southwest Airlines WN 2619 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-04-12 through 2026-05-17 |
| Sun
10:35
Orlando (MCO)
12:25
Chicago Midway (MDW) Southwest Airlines WN 2619 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Operates only on 2026-05-31 |
| Sun
12:05
Orlando (MCO)
13:55
Chicago Midway (MDW) Southwest Airlines WN 2619 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-05-24 |
| Tue,Wed
11:00
Orlando (MCO)
12:45
Chicago Midway (MDW) Southwest Airlines WN 2653 Non-stop Boeing 737-800 (73H) 2:45 Effective 2026-06-09 through 2026-07-29 |
| Sun
06:45
Orlando (MCO)
08:30
Chicago Midway (MDW) Southwest Airlines WN 2654 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-06-07 through 2026-08-02 |
| Sat
07:00
Orlando (MCO)
08:50
Chicago Midway (MDW) Southwest Airlines WN 2654 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-06-06 through 2026-08-01 |
| Mon,Thu,Fri
07:25
Orlando (MCO)
09:15
Chicago Midway (MDW) Southwest Airlines WN 2654 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-06-04 through 2026-08-03 |
| Mon,Thu,Fri
13:00
Orlando (MCO)
14:40
Chicago Midway (MDW) Southwest Airlines WN 2657 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-06-04 through 2026-08-03 |
| Sat
13:25
Orlando (MCO)
15:10
Chicago Midway (MDW) Southwest Airlines WN 2657 Non-stop Boeing 737-800 (73H) 2:45 Effective 2026-06-06 through 2026-08-01 |
| Sun
17:30
Orlando (MCO)
19:30
Chicago Midway (MDW) Southwest Airlines WN 2657 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-06-07 through 2026-08-02 |
| Tue,Wed
14:30
Orlando (MCO)
16:20
Chicago Midway (MDW) Southwest Airlines WN 2658 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-06-09 through 2026-07-29 |
| Sat
15:25
Orlando (MCO)
17:20
Chicago Midway (MDW) Southwest Airlines WN 2658 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-06-06 through 2026-08-01 |
| Mon,Thu,Fri
15:40
Orlando (MCO)
17:30
Chicago Midway (MDW) Southwest Airlines WN 2658 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-06-04 through 2026-08-03 |
| Tue,Wed
16:20
Orlando (MCO)
18:15
Chicago Midway (MDW) Southwest Airlines WN 2659 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-06-09 through 2026-07-29 |
| Mon,Thu,Fri
18:10
Orlando (MCO)
20:10
Chicago Midway (MDW) Southwest Airlines WN 2659 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-06-04 through 2026-08-03 |
| Tue,Wed
18:15
Orlando (MCO)
20:15
Chicago Midway (MDW) Southwest Airlines WN 2660 Non-stop Boeing 737-800 (73H) 3:00 Effective 2026-06-09 through 2026-07-29 |
| Sat
18:25
Orlando (MCO)
20:20
Chicago Midway (MDW) Southwest Airlines WN 2660 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-06-06 through 2026-08-01 |
| Sun
18:50
Orlando (MCO)
20:45
Chicago Midway (MDW) Southwest Airlines WN 2660 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-06-07 through 2026-08-02 |
| Mon,Thu,Fri
19:30
Orlando (MCO)
21:20
Chicago Midway (MDW) Southwest Airlines WN 2660 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-06-04 through 2026-08-03 |
| Sun
07:45
Orlando (MCO)
09:30
Chicago Midway (MDW) Southwest Airlines WN 2835 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-06-07 through 2026-08-02 |
| Tue,Wed
08:00
Orlando (MCO)
09:50
Chicago Midway (MDW) Southwest Airlines WN 2835 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-06-09 through 2026-07-29 |
- 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.
