Southwest Airlines flights from Orlando (MCO) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Sun
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 2026-03-01 |
| Sun
11:55
Orlando (MCO)
13:40
Chicago Midway (MDW) Southwest Airlines WN 4333 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-09 through 2026-09-27 |
| Mon,Thu,Fri
13:50
Orlando (MCO)
15:35
Chicago Midway (MDW) Southwest Airlines WN 4333 Non-stop Boeing 737-700 (Scimitar Winglets) 2:45 Effective 2026-08-06 through 2026-09-28 |
| Sun
14:35
Orlando (MCO)
16:30
Chicago Midway (MDW) Southwest Airlines WN 4471 Non-stop Boeing 737-800 (73H) 2:55 Operates only on 2026-02-08 |
| Wed,Thu
07:30
Orlando (MCO)
09:20
Chicago Midway (MDW) Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-01 |
| Mon
10:05
Orlando (MCO)
11:55
Chicago Midway (MDW) Southwest Airlines WN 4535 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2026-01-05 |
| Sat
12:35
Orlando (MCO)
14:20
Chicago Midway (MDW) Southwest Airlines WN 4644 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-08 through 2026-09-26 |
| Tue,Wed
13:00
Orlando (MCO)
14:45
Chicago Midway (MDW) Southwest Airlines WN 4644 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-04 through 2026-09-30 |
| Sun
13:40
Orlando (MCO)
15:25
Chicago Midway (MDW) Southwest Airlines WN 4644 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-09 through 2026-09-27 |
| Mon,Thu,Fri
16:10
Orlando (MCO)
18:00
Chicago Midway (MDW) Southwest Airlines WN 4644 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-08-06 through 2026-09-28 |
| Fri
11:50
Orlando (MCO)
13:45
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Operates only on 2026-02-13 |
| Mon,Thu
12:00
Orlando (MCO)
13:55
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
12:00
Orlando (MCO)
13:55
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-02-20 through 2026-03-01 |
| Thu,Fri,Sun
12:25
Orlando (MCO)
14:20
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
12:25
Orlando (MCO)
14:20
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-19 through 2026-01-25 |
| Sun
12:25
Orlando (MCO)
14:20
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Operates only on 2026-02-01 |
| Mon,Thu,Fri
12:55
Orlando (MCO)
14:50
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-05 through 2026-02-09 |
| Tue,Thu,Sun
12:55
Orlando (MCO)
14:50
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-15 through 2026-02-19 |
| Mon
12:55
Orlando (MCO)
14:50
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-23 through 2026-03-02 |
| Sat
13:35
Orlando (MCO)
15:30
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-10 through 2026-01-31 |
| Sat
13:35
Orlando (MCO)
15:30
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Operates only on 2026-02-07 |
| Mon-Fri
14:35
Orlando (MCO)
16:30
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
14:35
Orlando (MCO)
16:30
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
14:35
Orlando (MCO)
16:30
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed
14:35
Orlando (MCO)
16:30
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-02-10 through 2026-02-11 |
| Tue,Wed
14:35
Orlando (MCO)
16:30
Chicago Midway (MDW) Southwest Airlines WN 4661 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-02-18 through 2026-03-04 |
| Thu,Fri,Sun
09:25
Orlando (MCO)
11:15
Chicago Midway (MDW) Southwest Airlines WN 4664 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-01-11 through 2026-01-16 |
| Mon
09:30
Orlando (MCO)
11:25
Chicago Midway (MDW) Southwest Airlines WN 4664 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Operates only on 2026-01-19 |
| Sun
09:30
Orlando (MCO)
11:25
Chicago Midway (MDW) Southwest Airlines WN 4664 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Operates only on 2026-02-01 |
| Sun
09:35
Orlando (MCO)
11:25
Chicago Midway (MDW) Southwest Airlines WN 4664 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-01-25 |
| Sun
09:40
Orlando (MCO)
11:30
Chicago Midway (MDW) Southwest Airlines WN 4664 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-02-15 |
| Mon,Thu,Fri
09:50
Orlando (MCO)
11:40
Chicago Midway (MDW) Southwest Airlines WN 4664 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-02-05 through 2026-02-09 |
| Mon,Tue,Thu
09:50
Orlando (MCO)
11:40
Chicago Midway (MDW) Southwest Airlines WN 4664 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-02-17 through 2026-02-23 |
| Mon
09:50
Orlando (MCO)
11:40
Chicago Midway (MDW) Southwest Airlines WN 4664 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-03-02 |
| Sat
10:15
Orlando (MCO)
12:10
Chicago Midway (MDW) Southwest Airlines WN 4664 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-01-10 through 2026-02-07 |
| Mon,Thu,Fri
08:10
Orlando (MCO)
10:00
Chicago Midway (MDW) Southwest Airlines WN 4729 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
08:10
Orlando (MCO)
10:00
Chicago Midway (MDW) Southwest Airlines WN 4729 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-02-20 through 2026-03-01 |
| Sat
08:35
Orlando (MCO)
10:25
Chicago Midway (MDW) Southwest Airlines WN 4729 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-02-14 through 2026-02-28 |
| Tue,Wed
20:10
Orlando (MCO)
22:00
Chicago Midway (MDW) Southwest Airlines WN 4762 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-06-09 through 2026-07-29 |
| Sat
20:40
Orlando (MCO)
22:30
Chicago Midway (MDW) Southwest Airlines WN 4762 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-06-06 through 2026-08-01 |
| Sun
22:00
Orlando (MCO)
23:45
Chicago Midway (MDW) Southwest Airlines WN 4762 Non-stop Boeing 737-800 (73H) 2:45 Effective 2026-06-07 through 2026-08-02 |
| Mon,Thu,Fri
22:55
Orlando (MCO)
00:40
Chicago Midway (MDW) Southwest Airlines WN 4762 Non-stop Boeing 737-700 (Scimitar Winglets) 2:45 Effective 2026-06-04 through 2026-08-03 The flight arrives 1 day after departure. |
| Thu,Fri,Sun
16:00
Orlando (MCO)
18:00
Chicago Midway (MDW) Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
16:00
Orlando (MCO)
18:00
Chicago Midway (MDW) Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
16:00
Orlando (MCO)
18:00
Chicago Midway (MDW) Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
16:00
Orlando (MCO)
18:00
Chicago Midway (MDW) Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
16:00
Orlando (MCO)
18:00
Chicago Midway (MDW) Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-02-17 through 2026-02-23 |
| Mon
16:00
Orlando (MCO)
18:00
Chicago Midway (MDW) Southwest Airlines WN 4806 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Operates only on 2026-03-02 |
| Sat
16:40
Orlando (MCO)
18:35
Chicago Midway (MDW) Southwest Airlines WN 4806 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-10 through 2026-01-31 |
| Sat
17:00
Orlando (MCO)
19:00
Chicago Midway (MDW) Southwest Airlines WN 4806 Non-stop Boeing 737-800 (73H) 3:00 Operates only on 2026-02-07 |
- 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.
