Southwest Airlines flights from Midway, Chicago (MDW) to San Jose (SJC).

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Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sun 17:45 Midway, Chicago (MDW) 20:20 San Jose (SJC) B
Southwest Airlines WN 189 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-10-05 through 2025-10-26
Thu 09:05 Midway, Chicago (MDW) 11:45 San Jose (SJC) B
Southwest Airlines WN 392 Non-stop Boeing 737-700 (Scimitar Winglets) 4:40 Operates only on 2025-11-27
Mon,Thu,Fri,Sun 07:50 Midway, Chicago (MDW) 10:35 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 07:50 Midway, Chicago (MDW) 10:35 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2025-11-21 through 2025-11-28
Fri,Sun 07:50 Midway, Chicago (MDW) 10:35 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2025-12-07 through 2025-12-14
Thu 07:50 Midway, Chicago (MDW) 10:35 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Operates only on 2025-12-18
Mon 07:50 Midway, Chicago (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-Wed 08:00 Midway, Chicago (MDW) 10:45 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 08:00 Midway, Chicago (MDW) 10:45 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2025-12-19 through 2026-01-04
Tue,Wed 08:45 Midway, Chicago (MDW) 11:30 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737-700 (Scimitar Winglets) 4:45 Effective 2025-11-04 through 2025-11-12
Mon-Thu 08:45 Midway, Chicago (MDW) 11:30 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737-700 (Scimitar Winglets) 4:45 Effective 2025-11-17 through 2025-11-20
Mon-Fri 08:45 Midway, Chicago (MDW) 11:30 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737-700 (Scimitar Winglets) 4:45 Effective 2025-12-02 through 2025-12-11
Mon-Wed 08:45 Midway, Chicago (MDW) 11:30 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737-700 (Scimitar Winglets) 4:45 Effective 2025-12-15 through 2025-12-17
Wed,Thu 08:45 Midway, Chicago (MDW) 11:30 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737-700 (Scimitar Winglets) 4:45 Effective 2025-12-24 through 2026-01-01
Sun 14:30 Midway, Chicago (MDW) 17:10 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Operates only on 2025-11-30
Sat 15:00 Midway, Chicago (MDW) 17:40 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737-700 (Scimitar Winglets) 4:40 Effective 2025-11-08 through 2025-11-15
Sat 15:00 Midway, Chicago (MDW) 17:40 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737-700 (Scimitar Winglets) 4:40 Effective 2025-12-06 through 2025-12-13
Sat 19:35 Midway, Chicago (MDW) 22:15 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-11-22 through 2025-11-29
Sat 19:35 Midway, Chicago (MDW) 22:15 San Jose (SJC) B
Southwest Airlines WN 781 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-12-20 through 2026-01-03
Tue,Wed 16:00 Midway, Chicago (MDW) 18:35 San Jose (SJC) B
Southwest Airlines WN 786 Non-stop Boeing 737-700 (73W) 4:35 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 07:50 Midway, Chicago (MDW) 10:20 San Jose (SJC) B
Southwest Airlines WN 1291 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-10-02 through 2025-10-31
Tue,Wed 08:25 Midway, Chicago (MDW) 11:00 San Jose (SJC) B
Southwest Airlines WN 1454 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-06-10 through 2025-07-30
Fri 15:00 Midway, Chicago (MDW) 17:35 San Jose (SJC) B
Southwest Airlines WN 1454 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Operates only on 2025-07-04
Mon,Thu,Fri 15:55 Midway, Chicago (MDW) 18:30 San Jose (SJC) B
Southwest Airlines WN 1454 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-06-05 through 2025-06-19
Mon,Thu,Fri 15:55 Midway, Chicago (MDW) 18:30 San Jose (SJC) B
Southwest Airlines WN 1454 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-07-07 through 2025-08-04
Mon,Thu,Fri 08:25 Midway, Chicago (MDW) 11:00 San Jose (SJC) B
Southwest Airlines WN 1526 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Valid until 2025-06-02
Tue,Wed 17:05 Midway, Chicago (MDW) 19:40 San Jose (SJC) B
Southwest Airlines WN 1526 Non-stop Boeing 737-700 (73W) 4:35 Valid until 2025-06-04
Sun 17:50 Midway, Chicago (MDW) 20:30 San Jose (SJC) B
Southwest Airlines WN 1873 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Operates only on 2025-05-25
Tue,Wed 08:40 Midway, Chicago (MDW) 11:15 San Jose (SJC) B
Southwest Airlines WN 1964 Non-stop Boeing 737-700 (73W) 4:35 Valid until 2025-06-04
Tue,Wed 08:25 Midway, Chicago (MDW) 10:55 San Jose (SJC) B
Southwest Airlines WN 2008 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-08-05 through 2025-10-01
Sun 10:00 Midway, Chicago (MDW) 12:30 San Jose (SJC) B
Southwest Airlines WN 2008 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Operates only on 2025-08-31
Sat 15:35 Midway, Chicago (MDW) 18:05 San Jose (SJC) B
Southwest Airlines WN 2008 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-08-09 through 2025-09-27
Sun 19:50 Midway, Chicago (MDW) 22:20 San Jose (SJC) B
Southwest Airlines WN 2008 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-08-10 through 2025-08-24
Sun 19:50 Midway, Chicago (MDW) 22:20 San Jose (SJC) B
Southwest Airlines WN 2008 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-09-07 through 2025-09-28
Sun 17:25 Midway, Chicago (MDW) 20:00 San Jose (SJC) B
Southwest Airlines WN 2022 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-06-08 through 2025-08-03
Fri 08:15 Midway, Chicago (MDW) 10:50 San Jose (SJC) B
Southwest Airlines WN 2346 Non-stop Boeing 737-700 (73W) 4:35 Operates only on 2025-07-04
Tue,Wed 17:25 Midway, Chicago (MDW) 19:55 San Jose (SJC) B
Southwest Airlines WN 2928 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-10-07 through 2025-10-29
Sun 09:30 Midway, Chicago (MDW) 12:05 San Jose (SJC) B
Southwest Airlines WN 2958 Non-stop Boeing 737-700 (73W) 4:35 Valid until 2025-05-18
Sun 09:30 Midway, Chicago (MDW) 12:05 San Jose (SJC) B
Southwest Airlines WN 2958 Non-stop Boeing 737-700 (73W) 4:35 Operates only on 2025-06-01
Sat 16:30 Midway, Chicago (MDW) 19:05 San Jose (SJC) B
Southwest Airlines WN 2958 Non-stop Boeing 737-700 (73W) 4:35 Valid until 2025-05-31
Mon,Thu,Fri 18:25 Midway, Chicago (MDW) 21:00 San Jose (SJC) B
Southwest Airlines WN 2958 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Valid until 2025-06-02
Tue,Wed 17:40 Midway, Chicago (MDW) 20:10 San Jose (SJC) B
Southwest Airlines WN 3762 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-08-05 through 2025-10-01
Mon,Thu,Fri 19:55 Midway, Chicago (MDW) 22:25 San Jose (SJC) B
Southwest Airlines WN 3762 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-08-07 through 2025-09-29
Sat 16:10 Midway, Chicago (MDW) 18:40 San Jose (SJC) B
Southwest Airlines WN 3811 Non-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2025-10-04 through 2025-11-01
Sat 07:45 Midway, Chicago (MDW) 10:15 San Jose (SJC) B
Southwest Airlines WN 3917 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-06-07 through 2025-08-02
Mon,Thu,Fri 10:25 Midway, Chicago (MDW) 12:55 San Jose (SJC) B
Southwest Airlines WN 3917 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 10:25 Midway, Chicago (MDW) 12:55 San Jose (SJC) B
Southwest Airlines WN 3917 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-07-07 through 2025-08-04
Tue,Wed 19:30 Midway, Chicago (MDW) 22:05 San Jose (SJC) B
Southwest Airlines WN 3917 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 20:05 Midway, Chicago (MDW) 22:40 San Jose (SJC) B
Southwest Airlines WN 3919 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 20:05 Midway, Chicago (MDW) 22:40 San Jose (SJC) B
Southwest Airlines WN 3919 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-07-07 through 2025-08-04
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Southwest Airlines flights from Midway, Chicago (MDW) to San Jose (SJC).
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Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2025-10-05 through 2025-10-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-11-27
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-04 through 2025-11-12
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-17 through 2025-11-20
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-02 through 2025-12-11
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 4:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-15 through 2025-12-17
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-24 through 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737-700 (73W)

Effective 2025-10-02 through 2025-10-31
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-07-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-05 through 2025-06-19
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737-700 (73W)

Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737-700 (73W)

Effective 2025-08-05 through 2025-10-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-08-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-08-09 through 2025-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-07-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737-700 (73W)

Effective 2025-10-07 through 2025-10-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:35, non-stop
Boeing 737-700 (73W)

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:35, non-stop
Boeing 737-700 (73W)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:35, non-stop
Boeing 737-700 (73W)

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-08-05 through 2025-10-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-08-07 through 2025-09-29
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-10-04 through 2025-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-06-07 through 2025-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)
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  • A domestic route departing from the Midway, Chicago 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 4:30 and 4:45.