Southwest Airlines flights from Orlando (MCO) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| 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 |
| Mon,Thu,Fri
11:40
Orlando (MCO)
13:35
Chicago Midway (MDW) Southwest Airlines WN 3862 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-03-05 through 2026-04-06 |
| Tue,Wed
11:55
Orlando (MCO)
13:50
Chicago Midway (MDW) Southwest Airlines WN 3862 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-03-10 through 2026-04-01 |
| Sun
13:50
Orlando (MCO)
15:50
Chicago Midway (MDW) Southwest Airlines WN 3862 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-03-08 through 2026-04-05 |
| Sat
14:50
Orlando (MCO)
16:45
Chicago Midway (MDW) Southwest Airlines WN 3862 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-07 through 2026-04-04 |
| Tue,Wed
13:30
Orlando (MCO)
15:15
Chicago Midway (MDW) Southwest Airlines WN 3874 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-06-09 through 2026-07-29 |
| Tue,Wed
08:30
Orlando (MCO)
10:25
Chicago Midway (MDW) Southwest Airlines WN 3883 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-10 through 2026-04-01 |
| Sat
16:45
Orlando (MCO)
18:45
Chicago Midway (MDW) Southwest Airlines WN 4015 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-03-07 through 2026-04-04 |
| Mon,Thu,Fri
17:00
Orlando (MCO)
19:05
Chicago Midway (MDW) Southwest Airlines WN 4015 Non-stop Boeing 737-800 (73H) 3:05 Effective 2026-03-05 through 2026-04-06 |
| Tue,Wed
17:20
Orlando (MCO)
19:20
Chicago Midway (MDW) Southwest Airlines WN 4015 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-03-10 through 2026-04-01 |
| Sun
18:25
Orlando (MCO)
20:25
Chicago Midway (MDW) Southwest Airlines WN 4015 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-03-08 through 2026-04-05 |
| Mon,Thu,Fri
09:10
Orlando (MCO)
10:55
Chicago Midway (MDW) Southwest Airlines WN 4037 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-06-04 through 2026-08-03 |
| Sun
09:30
Orlando (MCO)
11:15
Chicago Midway (MDW) Southwest Airlines WN 4037 Non-stop Boeing 737-800 (73H) 2:45 Effective 2026-06-07 through 2026-08-02 |
| Mon,Thu,Fri
19:00
Orlando (MCO)
20:55
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-02-05 through 2026-02-09 |
| Mon-Fri
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-06 through 2026-01-14 |
| Thu,Fri,Sun
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-01-11 through 2026-01-16 |
| Tue-Fri,Sun
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-18 through 2026-01-23 |
| Mon,Sun
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-01-19 through 2026-01-25 |
| Mon-Fri
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-26 through 2026-02-04 |
| Sun
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Operates only on 2026-02-01 |
| Tue,Sun
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-02-08 through 2026-02-10 |
| Mon,Wed-Fri
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-11 through 2026-02-18 |
| Tue,Sun
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-02-15 through 2026-02-17 |
| Tue-Fri,Sun
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-20 through 2026-02-27 |
| Mon
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-02-23 through 2026-03-02 |
| Tue,Wed
19:05
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-03 through 2026-03-04 |
| Thu
19:10
Orlando (MCO)
21:05
Chicago Midway (MDW) Southwest Airlines WN 4193 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Operates only on 2026-02-19 |
- 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.
