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

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sat 09:05 San Jose (SJC) B 15:10 Midway, Chicago (MDW)
Southwest Airlines WN 574 Non-stop Boeing 737-700 (73W) 4:05 Operates only on 2024-01-06
Mon,Thu,Fri 06:35 San Jose (SJC) B 12:40 Midway, Chicago (MDW)
Southwest Airlines WN 659 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-08-05 through 2024-09-30
Tue,Wed 06:35 San Jose (SJC) B 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 659 Non-stop Boeing 737-800 (73H) 4:10 Effective 2024-08-06 through 2024-10-02
Sun 06:40 San Jose (SJC) B 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 659 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-08-11 through 2024-08-25
Sun 06:40 San Jose (SJC) B 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 659 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-09-08 through 2024-09-29
Sun 06:55 San Jose (SJC) B 13:00 Midway, Chicago (MDW)
Southwest Airlines WN 659 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2024-09-01
Sat 06:45 San Jose (SJC) B 12:50 Midway, Chicago (MDW)
Southwest Airlines WN 663 Non-stop Boeing 737-700 (73W) 4:05 Effective 2024-01-13 through 2024-03-02
Sun 06:40 San Jose (SJC) B 12:50 Midway, Chicago (MDW)
Southwest Airlines WN 979 Non-stop Boeing 737-700 (73W) 4:10 Effective 2024-03-10 through 2024-04-07
Sat 06:50 San Jose (SJC) B 12:55 Midway, Chicago (MDW)
Southwest Airlines WN 979 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-03-09 through 2024-04-06
Tue,Wed 07:05 San Jose (SJC) B 13:10 Midway, Chicago (MDW)
Southwest Airlines WN 979 Non-stop Boeing 737-700 (73W) 4:05 Effective 2024-03-12 through 2024-04-03
Mon,Thu,Fri 08:00 San Jose (SJC) B 14:05 Midway, Chicago (MDW)
Southwest Airlines WN 979 Non-stop Boeing 737-700 (73W) 4:05 Effective 2024-03-07 through 2024-04-08
Tue,Wed 09:00 San Jose (SJC) B 15:10 Midway, Chicago (MDW)
Southwest Airlines WN 1060 Non-stop Boeing 737-800 (73H) 4:10 Effective 2024-01-09 through 2024-03-06
Sat 12:50 San Jose (SJC) B 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 1375 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-06-08 through 2024-08-03
Mon,Thu,Fri 13:55 San Jose (SJC) B 20:00 Midway, Chicago (MDW)
Southwest Airlines WN 1375 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-06-06 through 2024-07-01
Mon,Thu,Fri 13:55 San Jose (SJC) B 20:00 Midway, Chicago (MDW)
Southwest Airlines WN 1375 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-07-08 through 2024-08-02
Tue,Wed 14:10 San Jose (SJC) B 20:15 Midway, Chicago (MDW)
Southwest Airlines WN 1375 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-06-04 through 2024-07-31
Thu 14:20 San Jose (SJC) B 20:25 Midway, Chicago (MDW)
Southwest Airlines WN 1375 Non-stop Boeing 737-700 (73W) 4:05 Operates only on 2024-07-04
Sun 15:25 San Jose (SJC) B 21:35 Midway, Chicago (MDW)
Southwest Airlines WN 1375 Non-stop Boeing 737-800 (73H) 4:10 Effective 2024-06-09 through 2024-08-04
Mon,Sun 09:20 San Jose (SJC) B 15:25 Midway, Chicago (MDW)
Southwest Airlines WN 1514 Non-stop Boeing 737-800 (73H) 4:05 Valid until 2024-01-01
Wed-Fri,Sun 09:20 San Jose (SJC) B 15:25 Midway, Chicago (MDW)
Southwest Airlines WN 1514 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-01-03 through 2024-01-07
Sat 10:15 San Jose (SJC) B 16:20 Midway, Chicago (MDW)
Southwest Airlines WN 1603 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-08-10 through 2024-09-28
Mon,Thu,Fri 10:55 San Jose (SJC) B 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 1603 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-08-05 through 2024-09-30
Tue,Wed 11:15 San Jose (SJC) B 17:20 Midway, Chicago (MDW)
Southwest Airlines WN 1603 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-08-06 through 2024-10-02
Sun 12:00 San Jose (SJC) B 18:05 Midway, Chicago (MDW)
Southwest Airlines WN 1603 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2024-09-01
Sun 13:45 San Jose (SJC) B 19:50 Midway, Chicago (MDW)
Southwest Airlines WN 1603 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-08-11 through 2024-08-25
Sun 13:45 San Jose (SJC) B 19:50 Midway, Chicago (MDW)
Southwest Airlines WN 1603 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-09-08 through 2024-09-29
Mon,Thu,Fri 07:00 San Jose (SJC) B 13:10 Midway, Chicago (MDW)
Southwest Airlines WN 1828 Non-stop Boeing 737-700 (73W) 4:10 Effective 2024-01-08 through 2024-03-04
Fri 17:00 San Jose (SJC) B 23:05 Midway, Chicago (MDW)
Southwest Airlines WN 1873 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2024-07-05
Sun 09:05 San Jose (SJC) B 15:15 Midway, Chicago (MDW)
Southwest Airlines WN 2186 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2024-01-14 through 2024-03-03
Tue-Fri 11:45 San Jose (SJC) B 17:50 Midway, Chicago (MDW)
Southwest Airlines WN 2363 Non-stop Boeing 737-700 (73W) 4:05 Valid until 2024-01-02
Tue,Wed 18:35 San Jose (SJC) B 00:40 Midway, Chicago (MDW)
Southwest Airlines WN 2623 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-06-04 through 2024-07-31
The flight arrives 1 day after departure.
Mon,Thu,Fri 19:20 San Jose (SJC) B 01:25 Midway, Chicago (MDW)
Southwest Airlines WN 2623 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-06-06 through 2024-07-01
The flight arrives 1 day after departure.
Mon,Thu,Fri 19:20 San Jose (SJC) B 01:25 Midway, Chicago (MDW)
Southwest Airlines WN 2623 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-07-08 through 2024-08-02
The flight arrives 1 day after departure.
Fri 14:55 San Jose (SJC) B 21:00 Midway, Chicago (MDW)
Southwest Airlines WN 2638 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2024-07-05
Sat 06:35 San Jose (SJC) B 12:40 Midway, Chicago (MDW)
Southwest Airlines WN 2804 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-06-08 through 2024-08-03
Sun 06:35 San Jose (SJC) B 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 2804 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2024-06-09 through 2024-08-04
Tue,Wed 06:45 San Jose (SJC) B 12:50 Midway, Chicago (MDW)
Southwest Airlines WN 2804 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-06-04 through 2024-07-31
Mon,Thu,Fri 08:05 San Jose (SJC) B 14:10 Midway, Chicago (MDW)
Southwest Airlines WN 2804 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-06-06 through 2024-07-01
Mon,Thu,Fri 08:05 San Jose (SJC) B 14:10 Midway, Chicago (MDW)
Southwest Airlines WN 2804 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-07-08 through 2024-08-02
Thu 10:45 San Jose (SJC) B 16:50 Midway, Chicago (MDW)
Southwest Airlines WN 2804 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2024-07-04
Fri 10:00 San Jose (SJC) B 16:10 Midway, Chicago (MDW)
Southwest Airlines WN 3961 Non-stop Boeing 737-800 (73H) 4:10 Operates only on 2024-07-05
Mon,Thu,Fri 12:20 San Jose (SJC) B 18:25 Midway, Chicago (MDW)
Southwest Airlines WN 5229 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-04-11 through 2024-06-03
Tue,Wed 12:25 San Jose (SJC) B 18:30 Midway, Chicago (MDW)
Southwest Airlines WN 5229 Non-stop Boeing 737-700 (73W) 4:05 Effective 2024-04-09 through 2024-05-29
Tue,Wed 06:45 San Jose (SJC) B 12:50 Midway, Chicago (MDW)
Southwest Airlines WN 5972 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-04-09 through 2024-05-29
Mon,Thu,Fri 06:45 San Jose (SJC) B 12:55 Midway, Chicago (MDW)
Southwest Airlines WN 5972 Non-stop Boeing 737-800 (73H) 4:10 Effective 2024-04-11 through 2024-06-03
Sat 07:00 San Jose (SJC) B 13:10 Midway, Chicago (MDW)
Southwest Airlines WN 5972 Non-stop Boeing 737-700 (73W) 4:10 Effective 2024-04-13 through 2024-06-01
Sun 07:25 San Jose (SJC) B 13:30 Midway, Chicago (MDW)
Southwest Airlines WN 5972 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-04-14 through 2024-05-19
Sun 07:25 San Jose (SJC) B 13:30 Midway, Chicago (MDW)
Southwest Airlines WN 5972 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2024-06-02
Sun 07:40 San Jose (SJC) B 13:45 Midway, Chicago (MDW)
Southwest Airlines WN 5972 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2024-05-26
Non-Direct Flights:
Mon,Thu,Fri 10:30 San Jose (SJC) B 18:35 Midway, Chicago (MDW)
Southwest Airlines WN 106 1-stop Boeing 737 MAX 8 (7M8) 6:05 Effective 2024-04-11 through 2024-06-03
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Southwest Airlines flights from San Jose (SJC) to Midway, Chicago (MDW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Operates only on 2024-01-06
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, non-stop
Boeing 737-700 (73W)

Effective 2024-08-05 through 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Effective 2024-08-06 through 2024-10-02
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:10, non-stop
Boeing 737-800 (73H)

Effective 2024-08-11 through 2024-08-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-09-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Effective 2024-01-13 through 2024-03-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, non-stop
Boeing 737-700 (73W)

Effective 2024-03-10 through 2024-04-07
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:10, non-stop
Boeing 737-700 (73W)

Effective 2024-03-09 through 2024-04-06
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Effective 2024-03-12 through 2024-04-03
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-700 (73W)

Effective 2024-03-07 through 2024-04-08
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-700 (73W)

Effective 2024-01-09 through 2024-03-06
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:10, non-stop
Boeing 737-800 (73H)

Effective 2024-06-08 through 2024-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-06-06 through 2024-07-01
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-07-08 through 2024-08-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-06-04 through 2024-07-31
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Operates only on 2024-07-04
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-700 (73W)

Effective 2024-06-09 through 2024-08-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:10, non-stop
Boeing 737-800 (73H)

Valid until 2024-01-01
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Effective 2024-01-03 through 2024-01-07
Mon
-
Tue
-
Wed
Thu
Fri
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Effective 2024-08-10 through 2024-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-08-05 through 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-08-06 through 2024-10-02
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Operates only on 2024-09-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Effective 2024-08-11 through 2024-08-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-01-08 through 2024-03-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:10, non-stop
Boeing 737-700 (73W)

Operates only on 2024-07-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-01-14 through 2024-03-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2024-01-02
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-700 (73W)

Effective 2024-06-04 through 2024-07-31
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Effective 2024-06-06 through 2024-07-01
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Effective 2024-07-08 through 2024-08-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Operates only on 2024-07-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Effective 2024-06-08 through 2024-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Effective 2024-06-09 through 2024-08-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-06-04 through 2024-07-31
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-06-06 through 2024-07-01
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Effective 2024-07-08 through 2024-08-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Operates only on 2024-07-04
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-07-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 4:10, non-stop
Boeing 737-800 (73H)

Effective 2024-04-11 through 2024-06-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-04-09 through 2024-05-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-700 (73W)

Effective 2024-04-09 through 2024-05-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-04-11 through 2024-06-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:10, non-stop
Boeing 737-800 (73H)

Effective 2024-04-13 through 2024-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:10, non-stop
Boeing 737-700 (73W)

Effective 2024-04-14 through 2024-05-19
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-06-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-05-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Effective 2024-04-11 through 2024-06-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 6:05, 1-stop
Boeing 737 MAX 8 (7M8)
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  • A domestic route departing from the San Jose airport (SJC) and arriving at Midway, Chicago airport (MDW).
  • The flight distance is 1832 miles, or 2948 km.
  • The timezone of the departure airport is UTC-8 , 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 4:05 and 4:10.