Southwest Airlines flights from Orlando (MCO) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Non-Direct Flights: |
| Sun
07:50
Orlando (MCO)
11:25
Chicago Midway (MDW) Southwest Airlines WN 1514 1-stop Boeing 737-700 (Scimitar Winglets) 4:35 Effective 2026-03-08 through 2026-04-05 |
| Sat
15:50
Orlando (MCO)
19:30
Chicago Midway (MDW) Southwest Airlines WN 1707 1-stop Boeing 737-700 (Scimitar Winglets) 4:40 Effective 2026-02-14 through 2026-02-28 |
| Sat
17:10
Orlando (MCO)
21:45
Chicago Midway (MDW) Southwest Airlines WN 1723 1-stop Boeing 737 MAX 8 (7M8) 5:35 Valid until 2026-01-03 |
| Sun
14:10
Orlando (MCO)
17:35
Chicago Midway (MDW) Southwest Airlines WN 1734 1-stop Boeing 737-700 (Scimitar Winglets) 4:25 Effective 2026-06-07 through 2026-08-02 |
| Sun
13:50
Orlando (MCO)
17:10
Chicago Midway (MDW) Southwest Airlines WN 1764 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Operates only on 2026-05-24 |
| Sat
16:15
Orlando (MCO)
19:25
Chicago Midway (MDW) Southwest Airlines WN 1929 1-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-06-06 through 2026-08-01 |
| Tue,Wed
08:55
Orlando (MCO)
12:05
Chicago Midway (MDW) Southwest Airlines WN 2035 1-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-03-10 through 2026-04-01 |
| Mon,Tue,Fri,Sun
09:05
Orlando (MCO)
13:20
Chicago Midway (MDW) Southwest Airlines WN 2047 1-stop Boeing 737-800 (73H) 5:15 Valid until 2026-01-04 |
| Sat
12:20
Orlando (MCO)
16:35
Chicago Midway (MDW) Southwest Airlines WN 2047 1-stop Boeing 737-800 (73H) 5:15 Valid until 2026-01-03 |
| Mon-Fri
10:45
Orlando (MCO)
14:30
Chicago Midway (MDW) Southwest Airlines WN 2078 1-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
10:45
Orlando (MCO)
14:30
Chicago Midway (MDW) Southwest Airlines WN 2078 1-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
10:45
Orlando (MCO)
14:30
Chicago Midway (MDW) Southwest Airlines WN 2078 1-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed,Sun
10:45
Orlando (MCO)
14:30
Chicago Midway (MDW) Southwest Airlines WN 2078 1-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
10:45
Orlando (MCO)
14:30
Chicago Midway (MDW) Southwest Airlines WN 2078 1-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2026-02-18 through 2026-03-04 |
| Tue,Wed
15:15
Orlando (MCO)
19:30
Chicago Midway (MDW) Southwest Airlines WN 2094 1-stop Boeing 737-700 (Scimitar Winglets) 5:15 Effective 2026-04-07 through 2026-06-03 |
| Sun
16:00
Orlando (MCO)
20:15
Chicago Midway (MDW) Southwest Airlines WN 2094 1-stop Boeing 737-800 (73H) 5:15 Effective 2026-04-12 through 2026-05-17 |
| Sun
16:00
Orlando (MCO)
20:15
Chicago Midway (MDW) Southwest Airlines WN 2094 1-stop Boeing 737-800 (73H) 5:15 Operates only on 2026-05-31 |
| Mon,Thu,Fri
16:25
Orlando (MCO)
20:40
Chicago Midway (MDW) Southwest Airlines WN 2094 1-stop Boeing 737 MAX 8 (7M8) 5:15 Effective 2026-04-09 through 2026-06-01 |
| Sat
13:40
Orlando (MCO)
17:10
Chicago Midway (MDW) Southwest Airlines WN 2194 1-stop Boeing 737-800 (73H) 4:30 Effective 2026-04-11 through 2026-05-30 |
| Fri
20:30
Orlando (MCO)
23:50
Chicago Midway (MDW) Southwest Airlines WN 2218 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Operates only on 2026-01-02 |
| Mon-Fri
14:10
Orlando (MCO)
19:00
Chicago Midway (MDW) Southwest Airlines WN 2308 1-stop Boeing 737-700 (Scimitar Winglets) 5:50 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
14:10
Orlando (MCO)
19:00
Chicago Midway (MDW) Southwest Airlines WN 2308 1-stop Boeing 737-700 (Scimitar Winglets) 5:50 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
14:10
Orlando (MCO)
19:00
Chicago Midway (MDW) Southwest Airlines WN 2308 1-stop Boeing 737-700 (Scimitar Winglets) 5:50 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed,Sun
14:10
Orlando (MCO)
19:00
Chicago Midway (MDW) Southwest Airlines WN 2308 1-stop Boeing 737-700 (Scimitar Winglets) 5:50 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
14:10
Orlando (MCO)
19:00
Chicago Midway (MDW) Southwest Airlines WN 2308 1-stop Boeing 737-700 (Scimitar Winglets) 5:50 Effective 2026-02-18 through 2026-03-04 |
| Mon,Thu,Fri
14:20
Orlando (MCO)
17:40
Chicago Midway (MDW) Southwest Airlines WN 2385 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-04-09 through 2026-06-01 |
| Sat
17:50
Orlando (MCO)
21:35
Chicago Midway (MDW) Southwest Airlines WN 2432 1-stop Boeing 737-800 (73H) 4:45 Valid until 2026-01-03 |
| Mon,Thu,Fri
06:50
Orlando (MCO)
10:00
Chicago Midway (MDW) Southwest Airlines WN 2570 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-06-04 through 2026-08-03 |
| Mon
17:40
Orlando (MCO)
21:45
Chicago Midway (MDW) Southwest Airlines WN 2589 1-stop Boeing 737 MAX 8 (7M8) 5:05 Operates only on 2026-02-02 |
| Sat
16:10
Orlando (MCO)
19:35
Chicago Midway (MDW) Southwest Airlines WN 2613 1-stop Boeing 737-700 (Scimitar Winglets) 4:25 Effective 2026-02-14 through 2026-02-28 |
| Mon,Thu,Fri
08:00
Orlando (MCO)
12:05
Chicago Midway (MDW) Southwest Airlines WN 2646 1-stop Boeing 737 MAX 8 (7M8) 5:05 Effective 2026-04-09 through 2026-06-01 |
| Sun
07:20
Orlando (MCO)
11:05
Chicago Midway (MDW) Southwest Airlines WN 2667 1-stop Boeing 737-700 (Scimitar Winglets) 4:45 Effective 2026-06-07 through 2026-08-02 |
| Sat
07:50
Orlando (MCO)
12:05
Chicago Midway (MDW) Southwest Airlines WN 2673 1-stop Boeing 737 MAX 8 (7M8) 5:15 Effective 2026-06-06 through 2026-08-01 |
| Sat
14:50
Orlando (MCO)
19:15
Chicago Midway (MDW) Southwest Airlines WN 2679 1-stop Boeing 737-700 (Scimitar Winglets) 5:25 Effective 2026-06-06 through 2026-08-01 |
| Mon,Thu,Fri
16:10
Orlando (MCO)
20:25
Chicago Midway (MDW) Southwest Airlines WN 2693 1-stop Boeing 737-700 (Scimitar Winglets) 5:15 Effective 2026-06-04 through 2026-08-03 |
| Mon,Thu,Fri
13:45
Orlando (MCO)
17:50
Chicago Midway (MDW) Southwest Airlines WN 2717 1-stop Boeing 737 MAX 8 (7M8) 5:05 Effective 2026-06-04 through 2026-08-03 |
| Sat
10:30
Orlando (MCO)
15:15
Chicago Midway (MDW) Southwest Airlines WN 2729 1-stop Boeing 737 MAX 8 (7M8) 5:45 Effective 2026-02-14 through 2026-02-28 |
| Tue,Wed
15:55
Orlando (MCO)
19:50
Chicago Midway (MDW) Southwest Airlines WN 2801 1-stop Boeing 737-800 (73H) 4:55 Effective 2026-03-10 through 2026-04-01 |
| Sat
10:30
Orlando (MCO)
14:45
Chicago Midway (MDW) Southwest Airlines WN 2819 1-stop Boeing 737-700 (Scimitar Winglets) 5:15 Effective 2026-01-10 through 2026-02-07 |
| Sat
15:15
Orlando (MCO)
19:35
Chicago Midway (MDW) Southwest Airlines WN 2893 1-stop Boeing 737-800 (73H) 5:20 Effective 2026-02-14 through 2026-02-28 |
| Sat
13:35
Orlando (MCO)
16:50
Chicago Midway (MDW) Southwest Airlines WN 2909 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Effective 2026-06-06 through 2026-08-01 |
| Sun
16:40
Orlando (MCO)
20:30
Chicago Midway (MDW) Southwest Airlines WN 3049 1-stop Boeing 737-800 (73H) 4:50 Effective 2026-06-07 through 2026-08-02 |
| Sat
15:25
Orlando (MCO)
19:45
Chicago Midway (MDW) Southwest Airlines WN 3091 1-stop Boeing 737-700 (Scimitar Winglets) 5:20 Effective 2026-02-14 through 2026-02-28 |
| Mon,Thu,Fri
17:00
Orlando (MCO)
20:15
Chicago Midway (MDW) Southwest Airlines WN 3104 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Effective 2026-04-09 through 2026-06-01 |
| Sat
17:20
Orlando (MCO)
20:35
Chicago Midway (MDW) Southwest Airlines WN 3267 1-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-03-07 through 2026-04-04 |
| Mon,Thu,Fri
14:20
Orlando (MCO)
17:45
Chicago Midway (MDW) Southwest Airlines WN 3345 1-stop Boeing 737-700 (Scimitar Winglets) 4:25 Effective 2026-06-04 through 2026-08-03 |
| Tue,Wed
15:35
Orlando (MCO)
19:25
Chicago Midway (MDW) Southwest Airlines WN 3359 1-stop Boeing 737-700 (Scimitar Winglets) 4:50 Effective 2026-03-10 through 2026-04-01 |
| Mon,Thu,Fri
08:15
Orlando (MCO)
12:40
Chicago Midway (MDW) Southwest Airlines WN 3431 1-stop Boeing 737-800 (73H) 5:25 Effective 2026-03-05 through 2026-04-06 |
| Mon,Thu,Fri
15:55
Orlando (MCO)
20:45
Chicago Midway (MDW) Southwest Airlines WN 3443 1-stop Boeing 737-700 (Scimitar Winglets) 5:50 Effective 2026-03-05 through 2026-04-06 |
| Tue,Wed
19:10
Orlando (MCO)
00:05
Chicago Midway (MDW) Southwest Airlines WN 3443 1-stop Boeing 737-800 (73H) 5:55 Effective 2026-03-10 through 2026-04-01 The flight arrives 1 day after departure. |
- 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.
