All airlines flying from Chicago Midway (MDW) to San Diego (SAN).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Mon,Tue,Thu
08:00
Chicago Midway (MDW)
10:35
San Diego (SAN) 1 Southwest Airlines WN 2755 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-02-17 through 2026-02-23 |
| Mon
08:00
Chicago Midway (MDW)
10:35
San Diego (SAN) 1 Southwest Airlines WN 2755 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Operates only on 2026-03-02 |
| Sat
08:05
Chicago Midway (MDW)
10:40
San Diego (SAN) 1 Southwest Airlines WN 2755 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-02-14 through 2026-02-28 |
| Sat
08:25
Chicago Midway (MDW)
11:05
San Diego (SAN) 1 Southwest Airlines WN 2755 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2026-01-10 through 2026-02-07 |
| Mon-Fri
19:50
Chicago Midway (MDW)
22:20
San Diego (SAN) 1 Southwest Airlines WN 2755 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
19:50
Chicago Midway (MDW)
22:20
San Diego (SAN) 1 Southwest Airlines WN 2755 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
19:50
Chicago Midway (MDW)
22:20
San Diego (SAN) 1 Southwest Airlines WN 2755 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed,Sun
19:50
Chicago Midway (MDW)
22:20
San Diego (SAN) 1 Southwest Airlines WN 2755 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
19:50
Chicago Midway (MDW)
22:20
San Diego (SAN) 1 Southwest Airlines WN 2755 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-02-18 through 2026-03-04 |
| Mon,Thu,Fri
15:10
Chicago Midway (MDW)
17:40
San Diego (SAN) 1 Southwest Airlines WN 2756 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
15:10
Chicago Midway (MDW)
17:40
San Diego (SAN) 1 Southwest Airlines WN 2756 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-02-20 through 2026-03-01 |
| Sat
16:40
Chicago Midway (MDW)
19:10
San Diego (SAN) 1 Southwest Airlines WN 2756 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-02-14 through 2026-02-28 |
| Mon,Thu,Fri
06:15
Chicago Midway (MDW)
08:20
San Diego (SAN) 1 Southwest Airlines WN 2814 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-08-06 through 2026-09-28 |
| Sat
10:00
Chicago Midway (MDW)
12:10
San Diego (SAN) 1 Southwest Airlines WN 2814 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-08-08 through 2026-09-26 |
| Tue,Wed
10:05
Chicago Midway (MDW)
12:15
San Diego (SAN) 1 Southwest Airlines WN 2814 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-08-04 through 2026-09-30 |
| Sun
10:35
Chicago Midway (MDW)
12:40
San Diego (SAN) 1 Southwest Airlines WN 2814 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-08-09 through 2026-09-27 |
| Sun
06:05
Chicago Midway (MDW)
08:15
San Diego (SAN) 1 Southwest Airlines WN 2815 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-08-09 through 2026-09-27 |
| Mon,Thu,Fri
10:20
Chicago Midway (MDW)
12:30
San Diego (SAN) 1 Southwest Airlines WN 2815 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-08-06 through 2026-09-28 |
| Mon,Thu-Sat
20:55
Chicago Midway (MDW)
23:25
San Diego (SAN) 1 Southwest Airlines WN 2815 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-03-05 through 2026-04-06 |
| Sat
14:15
Chicago Midway (MDW)
16:20
San Diego (SAN) 1 Southwest Airlines WN 2816 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-08-08 through 2026-09-26 |
| Tue,Wed
15:05
Chicago Midway (MDW)
17:10
San Diego (SAN) 1 Southwest Airlines WN 2816 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-08-04 through 2026-09-30 |
| Mon,Thu,Fri
14:15
Chicago Midway (MDW)
16:25
San Diego (SAN) 1 Southwest Airlines WN 2883 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-06-04 through 2026-08-03 |
| Sat
20:40
Chicago Midway (MDW)
22:55
San Diego (SAN) 1 Southwest Airlines WN 2884 Non-stop Boeing 737-700 (Scimitar Winglets) 4:15 Effective 2026-06-06 through 2026-08-01 |
| Tue,Wed
21:05
Chicago Midway (MDW)
23:20
San Diego (SAN) 1 Southwest Airlines WN 2884 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-06-09 through 2026-07-29 |
| Mon,Thu,Fri,Sun
21:10
Chicago Midway (MDW)
23:25
San Diego (SAN) 1 Southwest Airlines WN 2884 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-06-04 through 2026-08-03 |
| Sun
20:50
Chicago Midway (MDW)
23:20
San Diego (SAN) 1 Southwest Airlines WN 2972 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-03-08 through 2026-04-05 |
| Mon,Thu,Fri
05:45
Chicago Midway (MDW)
07:50
San Diego (SAN) 1 Southwest Airlines WN 3103 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-06-04 through 2026-08-03 |
| Tue,Wed
06:00
Chicago Midway (MDW)
08:10
San Diego (SAN) 1 Southwest Airlines WN 3103 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-06-09 through 2026-07-29 |
| Sun
06:05
Chicago Midway (MDW)
08:15
San Diego (SAN) 1 Southwest Airlines WN 3103 Non-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-06-07 through 2026-08-02 |
| Mon,Thu,Fri
10:50
Chicago Midway (MDW)
13:20
San Diego (SAN) 1 Southwest Airlines WN 3287 Non-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
10:50
Chicago Midway (MDW)
13:20
San Diego (SAN) 1 Southwest Airlines WN 3287 Non-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2026-02-20 through 2026-03-01 |
| Sat
20:40
Chicago Midway (MDW)
23:10
San Diego (SAN) 1 Southwest Airlines WN 3289 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-02-14 through 2026-02-28 |
| Tue,Wed
17:15
Chicago Midway (MDW)
19:35
San Diego (SAN) 1 Southwest Airlines WN 3541 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-04-07 through 2026-06-03 |
| Mon,Thu,Fri
17:25
Chicago Midway (MDW)
19:45
San Diego (SAN) 1 Southwest Airlines WN 3541 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-04-09 through 2026-06-01 |
| Sat
18:10
Chicago Midway (MDW)
20:30
San Diego (SAN) 1 Southwest Airlines WN 3541 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-04-11 through 2026-05-30 |
| Mon,Thu,Fri
20:45
Chicago Midway (MDW)
23:10
San Diego (SAN) 1 Southwest Airlines WN 3591 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-04-09 through 2026-06-01 |
| Tue,Wed
05:45
Chicago Midway (MDW)
08:10
San Diego (SAN) 1 Southwest Airlines WN 3994 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-03-10 through 2026-04-01 |
| Mon,Thu,Fri
06:05
Chicago Midway (MDW)
08:35
San Diego (SAN) 1 Southwest Airlines WN 3994 Non-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2026-03-05 through 2026-04-06 |
| Sat
14:05
Chicago Midway (MDW)
16:35
San Diego (SAN) 1 Southwest Airlines WN 3994 Non-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2026-03-07 through 2026-04-04 |
| Mon,Thu,Fri
16:05
Chicago Midway (MDW)
18:35
San Diego (SAN) 1 Southwest Airlines WN 3996 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-03-05 through 2026-04-06 |
| Tue,Wed
17:10
Chicago Midway (MDW)
19:40
San Diego (SAN) 1 Southwest Airlines WN 3996 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-03-10 through 2026-04-01 |
| Sun
18:25
Chicago Midway (MDW)
20:55
San Diego (SAN) 1 Southwest Airlines WN 3996 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-03-08 through 2026-04-05 |
| Mon,Thu,Fri
10:00
Chicago Midway (MDW)
12:10
San Diego (SAN) 1 Southwest Airlines WN 4648 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-06-04 through 2026-08-03 |
| Sat
10:15
Chicago Midway (MDW)
12:20
San Diego (SAN) 1 Southwest Airlines WN 4648 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-06-06 through 2026-08-01 |
| Tue,Wed
10:20
Chicago Midway (MDW)
12:25
San Diego (SAN) 1 Southwest Airlines WN 4648 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-06-09 through 2026-07-29 |
| Sat
20:20
Chicago Midway (MDW)
22:40
San Diego (SAN) 1 Southwest Airlines WN 4670 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Valid until 2026-01-03 |
| Sat
18:05
Chicago Midway (MDW)
20:20
San Diego (SAN) 1 Southwest Airlines WN 4802 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-08-08 through 2026-09-26 |
| Sun
20:25
Chicago Midway (MDW)
22:35
San Diego (SAN) 1 Southwest Airlines WN 4802 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-08-09 through 2026-09-27 |
| Mon,Tue,Thu,Fri
20:45
Chicago Midway (MDW)
22:55
San Diego (SAN) 1 Southwest Airlines WN 4802 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-08-04 through 2026-09-29 |
| Non-Direct Flights: |
| Mon,Thu,Fri
16:05
Chicago Midway (MDW)
20:00
San Diego (SAN) 1 Southwest Airlines WN 199 1-stop Boeing 737-800 (73H) 5:55 Effective 2026-03-05 through 2026-04-06 |
- A domestic route departing from the Chicago Midway airport (MDW) and arriving at San Diego airport (SAN).
- The flight distance is 1724 miles, or 2774 km.
- The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-8 . 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 4:05 and 4:40.
