All airlines flying from Chicago Midway (MDW) to San Jose (SJC).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Sun
10:05
Chicago Midway (MDW)
12:30
San Jose (SJC) B Southwest Airlines WN 714 Non-stop Boeing 737-700 (Scimitar Winglets) 4:25 Effective 2026-06-07 through 2026-08-02 |
| Mon
07:50
Chicago Midway (MDW)
10:35
San Jose (SJC) B Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Operates only on 2026-01-05 |
| Mon,Tue,Fri,Sun
08:00
Chicago Midway (MDW)
10:45
San Jose (SJC) B Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Valid until 2026-01-04 |
| Wed,Thu
08:45
Chicago Midway (MDW)
11:30
San Jose (SJC) B Southwest Airlines WN 781 Non-stop Boeing 737-700 (73W) 4:45 Valid until 2026-01-01 |
| Sat
19:35
Chicago Midway (MDW)
22:15
San Jose (SJC) B Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Valid until 2026-01-03 |
| Tue,Wed
15:40
Chicago Midway (MDW)
18:15
San Jose (SJC) B Southwest Airlines WN 826 Non-stop Boeing 737-700 (Scimitar Winglets) 4:35 Effective 2026-04-07 through 2026-06-03 |
| Sat
17:20
Chicago Midway (MDW)
19:55
San Jose (SJC) B Southwest Airlines WN 1142 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-04-11 through 2026-05-30 |
| Sun
18:40
Chicago Midway (MDW)
21:15
San Jose (SJC) B Southwest Airlines WN 1142 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Operates only on 2026-05-24 |
| Sun
21:20
Chicago Midway (MDW)
23:55
San Jose (SJC) B Southwest Airlines WN 1142 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-04-12 through 2026-05-17 |
| Sun
21:20
Chicago Midway (MDW)
23:55
San Jose (SJC) B Southwest Airlines WN 1142 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Operates only on 2026-05-31 |
| Sun
20:00
Chicago Midway (MDW)
22:40
San Jose (SJC) B Southwest Airlines WN 1204 Non-stop Boeing 737-700 (Scimitar Winglets) 4:40 Effective 2026-03-08 through 2026-04-05 |
| Mon,Thu,Fri
10:10
Chicago Midway (MDW)
12:45
San Jose (SJC) B Southwest Airlines WN 1284 Non-stop Boeing 737-700 (Scimitar Winglets) 4:35 Effective 2026-04-09 through 2026-06-01 |
| Sun
10:15
Chicago Midway (MDW)
12:50
San Jose (SJC) B Southwest Airlines WN 1284 Non-stop Boeing 737-700 (Scimitar Winglets) 4:35 Effective 2026-04-12 through 2026-05-17 |
| Sun
10:15
Chicago Midway (MDW)
12:50
San Jose (SJC) B Southwest Airlines WN 1284 Non-stop Boeing 737-700 (Scimitar Winglets) 4:35 Operates only on 2026-05-31 |
| Tue,Wed
10:20
Chicago Midway (MDW)
12:55
San Jose (SJC) B Southwest Airlines WN 1284 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-04-07 through 2026-06-03 |
| Sun
11:05
Chicago Midway (MDW)
13:40
San Jose (SJC) B Southwest Airlines WN 1284 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Operates only on 2026-05-24 |
| Tue,Wed
20:55
Chicago Midway (MDW)
23:25
San Jose (SJC) B Southwest Airlines WN 1662 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-06-09 through 2026-07-29 |
| Thu,Fri,Sun
08:05
Chicago Midway (MDW)
10:55
San Jose (SJC) B Southwest Airlines WN 2553 Non-stop Boeing 737-700 (Scimitar Winglets) 4:50 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
08:05
Chicago Midway (MDW)
10:55
San Jose (SJC) B Southwest Airlines WN 2553 Non-stop Boeing 737-700 (Scimitar Winglets) 4:50 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
08:05
Chicago Midway (MDW)
10:55
San Jose (SJC) B Southwest Airlines WN 2553 Non-stop Boeing 737-700 (Scimitar Winglets) 4:50 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
08:05
Chicago Midway (MDW)
10:55
San Jose (SJC) B Southwest Airlines WN 2553 Non-stop Boeing 737-700 (Scimitar Winglets) 4:50 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
08:05
Chicago Midway (MDW)
10:55
San Jose (SJC) B Southwest Airlines WN 2553 Non-stop Boeing 737-700 (Scimitar Winglets) 4:50 Effective 2026-02-17 through 2026-02-23 |
| Mon
08:05
Chicago Midway (MDW)
10:55
San Jose (SJC) B Southwest Airlines WN 2553 Non-stop Boeing 737-700 (Scimitar Winglets) 4:50 Operates only on 2026-03-02 |
| Sat
08:35
Chicago Midway (MDW)
11:30
San Jose (SJC) B Southwest Airlines WN 2553 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-01-10 through 2026-02-07 |
| Sat
20:25
Chicago Midway (MDW)
22:55
San Jose (SJC) B Southwest Airlines WN 2659 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-06-06 through 2026-08-01 |
| Mon,Thu,Fri
20:50
Chicago Midway (MDW)
23:25
San Jose (SJC) B Southwest Airlines WN 2659 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-06-04 through 2026-08-03 |
| Sun
21:25
Chicago Midway (MDW)
23:55
San Jose (SJC) B Southwest Airlines WN 2659 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-06-07 through 2026-08-02 |
| Sun
10:10
Chicago Midway (MDW)
12:35
San Jose (SJC) B Southwest Airlines WN 2830 Non-stop Boeing 737-700 (Scimitar Winglets) 4:25 Effective 2026-08-09 through 2026-09-27 |
| Mon,Thu,Fri
10:15
Chicago Midway (MDW)
12:45
San Jose (SJC) B Southwest Airlines WN 2830 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-08-06 through 2026-09-28 |
| Sat
13:15
Chicago Midway (MDW)
15:45
San Jose (SJC) B Southwest Airlines WN 2830 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-08-08 through 2026-09-26 |
| Mon,Thu,Fri
10:05
Chicago Midway (MDW)
12:45
San Jose (SJC) B Southwest Airlines WN 3372 Non-stop Boeing 737-700 (Scimitar Winglets) 4:40 Effective 2026-03-05 through 2026-04-06 |
| Sat
10:10
Chicago Midway (MDW)
12:50
San Jose (SJC) B Southwest Airlines WN 3372 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2026-03-07 through 2026-04-04 |
| Sun
10:20
Chicago Midway (MDW)
13:00
San Jose (SJC) B Southwest Airlines WN 3372 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2026-03-08 through 2026-04-05 |
| Tue,Wed
10:30
Chicago Midway (MDW)
13:10
San Jose (SJC) B Southwest Airlines WN 3372 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2026-03-10 through 2026-04-01 |
| Mon,Thu,Fri
20:25
Chicago Midway (MDW)
23:00
San Jose (SJC) B Southwest Airlines WN 3385 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-04-09 through 2026-06-01 |
| Tue
10:20
Chicago Midway (MDW)
12:45
San Jose (SJC) B Southwest Airlines WN 3502 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-08-04 through 2026-09-29 |
| Wed
10:20
Chicago Midway (MDW)
12:45
San Jose (SJC) B Southwest Airlines WN 3532 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-08-05 through 2026-09-30 |
| Mon,Thu,Fri
20:50
Chicago Midway (MDW)
23:20
San Jose (SJC) B Southwest Airlines WN 3532 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-08-06 through 2026-09-28 |
| Mon-Fri
10:05
Chicago Midway (MDW)
12:30
San Jose (SJC) B Southwest Airlines WN 3752 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-06-04 through 2026-08-03 |
| Sat
10:20
Chicago Midway (MDW)
12:45
San Jose (SJC) B Southwest Airlines WN 3752 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-06-06 through 2026-08-01 |
| Sat
18:25
Chicago Midway (MDW)
20:55
San Jose (SJC) B Southwest Airlines WN 3810 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-08-08 through 2026-09-26 |
| Tue,Wed
20:30
Chicago Midway (MDW)
23:00
San Jose (SJC) B Southwest Airlines WN 3810 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-08-04 through 2026-09-30 |
| Mon,Thu,Fri
20:00
Chicago Midway (MDW)
22:40
San Jose (SJC) B Southwest Airlines WN 4006 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2026-03-05 through 2026-04-06 |
| Tue,Wed
21:00
Chicago Midway (MDW)
23:45
San Jose (SJC) B Southwest Airlines WN 4006 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2026-03-10 through 2026-04-01 |
| Mon,Thu,Fri
08:00
Chicago Midway (MDW)
10:50
San Jose (SJC) B Southwest Airlines WN 4444 Non-stop Boeing 737 MAX 8 (7M8) 4:50 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
08:00
Chicago Midway (MDW)
10:50
San Jose (SJC) B Southwest Airlines WN 4444 Non-stop Boeing 737 MAX 8 (7M8) 4:50 Effective 2026-02-20 through 2026-03-01 |
| Sat
08:05
Chicago Midway (MDW)
10:55
San Jose (SJC) B Southwest Airlines WN 4444 Non-stop Boeing 737 MAX 8 (7M8) 4:50 Effective 2026-02-14 through 2026-02-28 |
| Sun
20:40
Chicago Midway (MDW)
23:10
San Jose (SJC) B Southwest Airlines WN 4996 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-08-09 through 2026-09-27 |
| Non-Direct Flights: |
| Thu,Fri,Sun
17:00
Chicago Midway (MDW)
21:15
San Jose (SJC) B Southwest Airlines WN 864 1-stop Boeing 737 MAX 8 (7M8) 6:15 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
17:00
Chicago Midway (MDW)
21:15
San Jose (SJC) B Southwest Airlines WN 864 1-stop Boeing 737 MAX 8 (7M8) 6:15 Effective 2026-01-19 through 2026-01-25 |
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- A domestic route departing from the Chicago Midway airport (MDW) and arriving at San Jose airport (SJC).
- The flight distance is 1832 miles, or 2948 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 4:25 and 4:55.
