All airlines flying from Orlando (MCO) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Sat
07:15
Orlando (MCO)
09:05
Chicago Midway (MDW) Southwest Airlines WN 1464 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-03 |
| Thu
09:30
Orlando (MCO)
11:20
Chicago Midway (MDW) Southwest Airlines WN 1464 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-01 |
| Sun
15:40
Orlando (MCO)
17:44
Chicago Midway (MDW) Frontier Airlines F9 1535 Non-stop Airbus A320neo (32N) 3:04 Operates only on 2026-03-29 |
| Thu,Sun
17:49
Orlando (MCO)
19:52
Chicago Midway (MDW) Frontier Airlines F9 1535 Non-stop Airbus A320neo (32N) 3:03 Effective 2026-02-01 through 2026-02-05 |
| Wed,Thu
16:35
Orlando (MCO)
18:25
Chicago Midway (MDW) Southwest Airlines WN 1550 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-01 |
| Mon,Thu,Fri
10:05
Orlando (MCO)
12:00
Chicago Midway (MDW) Southwest Airlines WN 1669 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-05 through 2026-04-06 |
| Tue,Wed
10:10
Orlando (MCO)
12:05
Chicago Midway (MDW) Southwest Airlines WN 1669 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-03-10 through 2026-04-01 |
| Sat
12:45
Orlando (MCO)
14:40
Chicago Midway (MDW) Southwest Airlines WN 1669 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-07 through 2026-04-04 |
| Mon-Fri
07:25
Orlando (MCO)
09:20
Chicago Midway (MDW) Southwest Airlines WN 1674 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
07:25
Orlando (MCO)
09:20
Chicago Midway (MDW) Southwest Airlines WN 1674 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
07:25
Orlando (MCO)
09:20
Chicago Midway (MDW) Southwest Airlines WN 1674 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed,Sun
07:25
Orlando (MCO)
09:20
Chicago Midway (MDW) Southwest Airlines WN 1674 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
07:25
Orlando (MCO)
09:20
Chicago Midway (MDW) Southwest Airlines WN 1674 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-18 through 2026-03-04 |
| Tue
16:45
Orlando (MCO)
18:40
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737-800 (73H) 2:55 Operates only on 2026-01-06 |
| Mon-Fri
16:45
Orlando (MCO)
18:40
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-07 through 2026-01-14 |
| Tue-Fri,Sun
16:45
Orlando (MCO)
18:40
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
16:45
Orlando (MCO)
18:40
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed,Sun
16:45
Orlando (MCO)
18:40
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
16:45
Orlando (MCO)
18:40
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-18 through 2026-03-04 |
| Sat
20:20
Orlando (MCO)
22:10
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-01-10 through 2026-02-07 |
| Thu,Fri,Sun
20:35
Orlando (MCO)
22:25
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
20:35
Orlando (MCO)
22:25
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
20:35
Orlando (MCO)
22:25
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
20:35
Orlando (MCO)
22:25
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
20:35
Orlando (MCO)
22:25
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-02-17 through 2026-02-23 |
| Mon
20:35
Orlando (MCO)
22:25
Chicago Midway (MDW) Southwest Airlines WN 1733 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-03-02 |
| Mon,Thu,Fri
12:50
Orlando (MCO)
14:45
Chicago Midway (MDW) Southwest Airlines WN 1739 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-05 through 2026-04-06 |
| Wed,Thu
12:40
Orlando (MCO)
14:30
Chicago Midway (MDW) Southwest Airlines WN 1747 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-01 |
| Mon
15:15
Orlando (MCO)
17:05
Chicago Midway (MDW) Southwest Airlines WN 1747 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Operates only on 2026-01-05 |
| Sat
21:55
Orlando (MCO)
23:50
Chicago Midway (MDW) Southwest Airlines WN 1780 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-03-07 through 2026-04-04 |
| Sat
17:35
Orlando (MCO)
19:30
Chicago Midway (MDW) Southwest Airlines WN 1823 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-03-07 through 2026-04-04 |
| Mon,Thu,Fri
17:05
Orlando (MCO)
19:00
Chicago Midway (MDW) Southwest Airlines WN 2046 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-04-09 through 2026-06-01 |
| Tue,Wed
17:50
Orlando (MCO)
19:45
Chicago Midway (MDW) Southwest Airlines WN 2046 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-04-07 through 2026-06-03 |
| Sat
18:30
Orlando (MCO)
20:25
Chicago Midway (MDW) Southwest Airlines WN 2046 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-04-11 through 2026-05-30 |
| Sun
18:35
Orlando (MCO)
20:30
Chicago Midway (MDW) Southwest Airlines WN 2046 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-04-12 through 2026-05-17 |
| Sun
18:35
Orlando (MCO)
20:30
Chicago Midway (MDW) Southwest Airlines WN 2046 Non-stop Boeing 737-800 (73H) 2:55 Operates only on 2026-05-31 |
| Wed,Thu
14:45
Orlando (MCO)
16:35
Chicago Midway (MDW) Southwest Airlines WN 2094 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-01 |
| Sat
20:10
Orlando (MCO)
22:00
Chicago Midway (MDW) Southwest Airlines WN 2094 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-03 |
| Mon,Tue,Fri,Sun
20:35
Orlando (MCO)
22:25
Chicago Midway (MDW) Southwest Airlines WN 2094 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-04 |
| Tue
08:10
Orlando (MCO)
10:00
Chicago Midway (MDW) Southwest Airlines WN 2108 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Operates only on 2026-01-27 |
| Sat
15:05
Orlando (MCO)
16:55
Chicago Midway (MDW) Southwest Airlines WN 2299 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-03 |
| Mon,Tue,Fri,Sun
17:25
Orlando (MCO)
19:15
Chicago Midway (MDW) Southwest Airlines WN 2299 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-04 |
| Sun
06:45
Orlando (MCO)
08:40
Chicago Midway (MDW) Southwest Airlines WN 2300 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-08 through 2026-04-05 |
| Sat
07:10
Orlando (MCO)
09:10
Chicago Midway (MDW) Southwest Airlines WN 2300 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-03-07 through 2026-04-04 |
| Mon,Thu,Fri
07:15
Orlando (MCO)
09:15
Chicago Midway (MDW) Southwest Airlines WN 2300 Non-stop Boeing 737 MAX 8 (7M8) 3:00 Effective 2026-03-05 through 2026-04-06 |
| Tue,Wed
07:15
Orlando (MCO)
09:15
Chicago Midway (MDW) Southwest Airlines WN 2300 Non-stop Boeing 737-800 (73H) 3:00 Effective 2026-03-10 through 2026-04-01 |
| Sun
09:50
Orlando (MCO)
11:40
Chicago Midway (MDW) Southwest Airlines WN 2403 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2026-05-24 |
| Sat
08:35
Orlando (MCO)
10:30
Chicago Midway (MDW) Southwest Airlines WN 2540 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-03-07 through 2026-04-04 |
| Sun
10:15
Orlando (MCO)
12:10
Chicago Midway (MDW) Southwest Airlines WN 2540 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-03-08 through 2026-04-05 |
| Tue,Wed
07:10
Orlando (MCO)
09:00
Chicago Midway (MDW) Southwest Airlines WN 2560 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.
