All airlines flying from Orlando (MCO) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Sat
20:25
Orlando (MCO)
22:15
Chicago Midway (MDW) Southwest Airlines WN 138 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-04-11 through 2026-05-30 |
| Mon,Thu,Fri
21:50
Orlando (MCO)
23:40
Chicago Midway (MDW) Southwest Airlines WN 138 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-04-09 through 2026-06-01 |
| Sat
09:10
Orlando (MCO)
11:00
Chicago Midway (MDW) Southwest Airlines WN 290 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-08-08 through 2026-09-26 |
| Tue,Wed
10:20
Orlando (MCO)
12:05
Chicago Midway (MDW) Southwest Airlines WN 290 Non-stop Boeing 737-800 (73H) 2:45 Effective 2026-08-04 through 2026-09-30 |
| Mon,Thu,Fri
06:55
Orlando (MCO)
08:45
Chicago Midway (MDW) Southwest Airlines WN 359 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-08-06 through 2026-09-28 |
| Tue,Wed
07:35
Orlando (MCO)
09:20
Chicago Midway (MDW) Southwest Airlines WN 359 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-04 through 2026-09-30 |
| Sun
08:00
Orlando (MCO)
09:45
Chicago Midway (MDW) Southwest Airlines WN 359 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-09 through 2026-09-27 |
| Mon,Thu,Fri
22:50
Orlando (MCO)
00:45
Chicago Midway (MDW) Southwest Airlines WN 416 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-05 through 2026-04-06 The flight arrives 1 day after departure. |
| Sun
22:55
Orlando (MCO)
00:50
Chicago Midway (MDW) Southwest Airlines WN 416 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-03-08 through 2026-04-05 The flight arrives 1 day after departure. |
| Sat
15:30
Orlando (MCO)
17:15
Chicago Midway (MDW) Southwest Airlines WN 424 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-08 through 2026-09-26 |
| Tue,Wed
15:50
Orlando (MCO)
17:40
Chicago Midway (MDW) Southwest Airlines WN 424 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-08-04 through 2026-09-30 |
| Tue,Wed
15:50
Orlando (MCO)
17:45
Chicago Midway (MDW) Southwest Airlines WN 498 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-03-10 through 2026-04-01 |
| Sat
11:45
Orlando (MCO)
13:35
Chicago Midway (MDW) Southwest Airlines WN 519 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Operates only on 2026-01-03 |
| Wed,Thu
17:40
Orlando (MCO)
19:30
Chicago Midway (MDW) Southwest Airlines WN 549 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-01 |
| Mon
18:40
Orlando (MCO)
20:30
Chicago Midway (MDW) Southwest Airlines WN 549 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2026-01-05 |
| Mon,Tue,Fri,Sun
18:45
Orlando (MCO)
20:35
Chicago Midway (MDW) Southwest Airlines WN 549 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-04 |
| Sat
19:10
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 549 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-03 |
| Mon,Thu,Fri
20:55
Orlando (MCO)
22:40
Chicago Midway (MDW) Southwest Airlines WN 693 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-06 through 2026-09-28 |
| Sat
16:40
Orlando (MCO)
18:35
Chicago Midway (MDW) Southwest Airlines WN 823 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Effective 2026-02-14 through 2026-02-28 |
| Mon
12:25
Orlando (MCO)
14:15
Chicago Midway (MDW) Southwest Airlines WN 1021 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-01-05 |
| Thu
20:25
Orlando (MCO)
22:15
Chicago Midway (MDW) Southwest Airlines WN 1057 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-02-12 |
| Fri
20:25
Orlando (MCO)
22:15
Chicago Midway (MDW) Southwest Airlines WN 1057 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Operates only on 2026-02-13 |
| Thu,Fri,Sun
20:25
Orlando (MCO)
22:15
Chicago Midway (MDW) Southwest Airlines WN 1057 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Effective 2026-02-20 through 2026-03-01 |
| Mon
20:35
Orlando (MCO)
22:25
Chicago Midway (MDW) Southwest Airlines WN 1057 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-02-16 |
| Sat
21:30
Orlando (MCO)
23:25
Chicago Midway (MDW) Southwest Airlines WN 1057 Non-stop Boeing 737 MAX 8 (7M8) 2:55 Operates only on 2026-02-14 |
| Sat
21:30
Orlando (MCO)
23:25
Chicago Midway (MDW) Southwest Airlines WN 1057 Non-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-02-21 through 2026-02-28 |
| Sun
16:10
Orlando (MCO)
18:00
Chicago Midway (MDW) Southwest Airlines WN 1142 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-05-24 |
| Sat
12:30
Orlando (MCO)
14:20
Chicago Midway (MDW) Southwest Airlines WN 1250 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-04-11 through 2026-05-30 |
| Mon,Thu,Fri
18:50
Orlando (MCO)
20:40
Chicago Midway (MDW) Southwest Airlines WN 1250 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-04-09 through 2026-06-01 |
| Tue,Wed
19:35
Orlando (MCO)
21:25
Chicago Midway (MDW) Southwest Airlines WN 1250 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-04-07 through 2026-06-03 |
| Sun
19:55
Orlando (MCO)
21:50
Chicago Midway (MDW) Southwest Airlines WN 1250 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-04-12 through 2026-05-17 |
| Sun
19:55
Orlando (MCO)
21:50
Chicago Midway (MDW) Southwest Airlines WN 1250 Non-stop Boeing 737-800 (73H) 2:55 Operates only on 2026-05-31 |
| Sun
20:55
Orlando (MCO)
22:45
Chicago Midway (MDW) Southwest Airlines WN 1250 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2026-05-24 |
| Mon,Thu,Fri
18:15
Orlando (MCO)
20:15
Chicago Midway (MDW) Southwest Airlines WN 1254 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-03-05 through 2026-04-06 |
| Tue,Wed
18:50
Orlando (MCO)
20:50
Chicago Midway (MDW) Southwest Airlines WN 1254 Non-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-03-10 through 2026-04-01 |
| Sat
16:30
Orlando (MCO)
18:20
Chicago Midway (MDW) Southwest Airlines WN 1255 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-06-06 through 2026-08-01 |
| Sat
15:30
Orlando (MCO)
17:25
Chicago Midway (MDW) Southwest Airlines WN 1364 Non-stop Boeing 737-800 (73H) 2:55 Effective 2026-02-14 through 2026-02-28 |
| Sat
10:30
Orlando (MCO)
12:10
Chicago Midway (MDW) Southwest Airlines WN 1418 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2026-06-06 through 2026-08-01 |
| Mon,Thu,Fri
08:15
Orlando (MCO)
10:00
Chicago Midway (MDW) Southwest Airlines WN 1429 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-06 through 2026-09-28 |
| Sat
19:10
Orlando (MCO)
20:55
Chicago Midway (MDW) Southwest Airlines WN 1429 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-08 through 2026-09-26 |
| Tue,Wed
19:15
Orlando (MCO)
21:00
Chicago Midway (MDW) Southwest Airlines WN 1429 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-08-04 through 2026-09-30 |
| Sun
19:35
Orlando (MCO)
21:20
Chicago Midway (MDW) Southwest Airlines WN 1429 Non-stop Boeing 737-700 (Scimitar Winglets) 2:45 Effective 2026-08-09 through 2026-09-27 |
| Thu
15:40
Orlando (MCO)
17:44
Chicago Midway (MDW) Frontier Airlines F9 1457 Non-stop Airbus A320neo (32N) 3:04 Effective 2026-03-12 through 2026-03-26 |
| Tue,Wed
16:05
Orlando (MCO)
18:13
Chicago Midway (MDW) Frontier Airlines F9 1457 Non-stop Airbus A320neo (32N) 3:08 Effective 2026-03-10 through 2026-03-31 |
| Mon,Fri
18:48
Orlando (MCO)
20:53
Chicago Midway (MDW) Frontier Airlines F9 1457 Non-stop Airbus A320neo (32N) 3:05 Effective 2026-03-06 through 2026-03-30 |
| Sun
18:56
Orlando (MCO)
20:53
Chicago Midway (MDW) Frontier Airlines F9 1457 Non-stop Airbus A320neo (32N) 2:57 Operates only on 2026-01-04 |
| Mon-Fri
19:58
Orlando (MCO)
21:58
Chicago Midway (MDW) Frontier Airlines F9 1457 Non-stop Airbus A320neo (32N) 3:00 Valid until 2026-01-05 |
| Sat
21:32
Orlando (MCO)
23:32
Chicago Midway (MDW) Frontier Airlines F9 1457 Non-stop Airbus A320neo (32N) 3:00 Effective 2026-03-07 through 2026-03-28 |
| Mon,Tue,Fri,Sun
06:50
Orlando (MCO)
08:40
Chicago Midway (MDW) Southwest Airlines WN 1464 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Valid until 2026-01-04 |
| Mon
06:55
Orlando (MCO)
08:45
Chicago Midway (MDW) Southwest Airlines WN 1464 Non-stop Boeing 737 MAX 8 (7M8) 2:50 Operates only on 2026-01-05 |
- 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.
