Southwest Airlines flights from Orlando (MCO) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Non-Direct Flights: |
| Sat
16:00
Orlando (MCO)
19:35
Chicago Midway (MDW) Southwest Airlines WN 3451 1-stop Boeing 737-700 (Scimitar Winglets) 4:35 Effective 2026-06-06 through 2026-08-01 |
| Mon
17:10
Orlando (MCO)
20:40
Chicago Midway (MDW) Southwest Airlines WN 3634 1-stop Boeing 737-700 (Scimitar Winglets) 4:30 Operates only on 2026-01-05 |
| Mon,Thu,Fri
16:10
Orlando (MCO)
20:15
Chicago Midway (MDW) Southwest Airlines WN 3709 1-stop Boeing 737 MAX 8 (7M8) 5:05 Effective 2026-03-05 through 2026-04-06 |
| Sat
16:20
Orlando (MCO)
20:25
Chicago Midway (MDW) Southwest Airlines WN 3709 1-stop Boeing 737-800 (73H) 5:05 Effective 2026-03-07 through 2026-04-04 |
| Sun
10:00
Orlando (MCO)
14:25
Chicago Midway (MDW) Southwest Airlines WN 3887 1-stop Boeing 737 MAX 8 (7M8) 5:25 Operates only on 2026-05-24 |
| Tue,Wed
15:25
Orlando (MCO)
19:45
Chicago Midway (MDW) Southwest Airlines WN 3971 1-stop Boeing 737 MAX 8 (7M8) 5:20 Effective 2026-03-10 through 2026-04-01 |
| Sat
16:10
Orlando (MCO)
20:25
Chicago Midway (MDW) Southwest Airlines WN 3971 1-stop Boeing 737-700 (Scimitar Winglets) 5:15 Effective 2026-03-07 through 2026-04-04 |
| Sun
16:15
Orlando (MCO)
20:35
Chicago Midway (MDW) Southwest Airlines WN 3971 1-stop Boeing 737 MAX 8 (7M8) 5:20 Effective 2026-03-08 through 2026-04-05 |
| Mon,Thu,Fri
16:20
Orlando (MCO)
20:40
Chicago Midway (MDW) Southwest Airlines WN 3971 1-stop Boeing 737-800 (73H) 5:20 Effective 2026-03-05 through 2026-04-06 |
| Mon,Thu,Fri
09:45
Orlando (MCO)
13:50
Chicago Midway (MDW) Southwest Airlines WN 4276 1-stop Boeing 737-800 (73H) 5:05 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
09:45
Orlando (MCO)
13:50
Chicago Midway (MDW) Southwest Airlines WN 4276 1-stop Boeing 737-800 (73H) 5:05 Effective 2026-02-20 through 2026-03-01 |
| Sat
12:30
Orlando (MCO)
17:00
Chicago Midway (MDW) Southwest Airlines WN 4990 1-stop Boeing 737-800 (73H) 5:30 Effective 2026-02-14 through 2026-02-28 |
| Sat
07:45
Orlando (MCO)
13:10
Chicago Midway (MDW) Southwest Airlines WN 762 2-stop Boeing 737 MAX 8 (7M8) 6:25 Effective 2026-06-06 through 2026-08-01 |
| Fri,Sun
15:00
Orlando (MCO)
19:40
Chicago Midway (MDW) Southwest Airlines WN 1253 2-stop Boeing 737-700 (Scimitar Winglets) 5:40 Effective 2026-01-02 through 2026-01-04 |
| Sat
14:25
Orlando (MCO)
19:35
Chicago Midway (MDW) Southwest Airlines WN 3054 2-stop Boeing 737-700 (Scimitar Winglets) 6:10 Operates only on 2026-01-03 |
- 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 3:05.
