All airlines flying from Chicago Midway (MDW) to San Jose (SJC).

FLIGHT SCHEDULE
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 2026-02-01 through 2026-02-06
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 2026-02-09 through 2026-02-15
Mon,Tue,Thu 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 2026-02-17 through 2026-02-23
Mon 17:00 Chicago Midway (MDW) 21:15 San Jose (SJC) B Southwest Airlines WN 864 1-stop Boeing 737 MAX 8 (7M8) 6:15 Operates only on 2026-03-02
Mon,Thu,Fri 07:15 Chicago Midway (MDW) 11:45 San Jose (SJC) B Southwest Airlines WN 1181 1-stop Boeing 737-800 (73H) 6:30 Effective 2026-03-05 through 2026-04-06
Sat 10:00 Chicago Midway (MDW) 14:25 San Jose (SJC) B Southwest Airlines WN 1186 1-stop Boeing 737-700 (Scimitar Winglets) 6:25 Effective 2026-04-11 through 2026-05-30
Mon,Thu,Fri 10:05 Chicago Midway (MDW) 14:15 San Jose (SJC) B Southwest Airlines WN 1390 1-stop Boeing 737-700 (Scimitar Winglets) 6:10 Effective 2026-04-09 through 2026-06-01
Mon 17:25 Chicago Midway (MDW) 22:50 San Jose (SJC) B Southwest Airlines WN 2144 1-stop Boeing 737 MAX 8 (7M8) 7:25 Operates only on 2026-01-05
Thu,Fri,Sun 08:05 Chicago Midway (MDW) 13:45 San Jose (SJC) B Southwest Airlines WN 2169 1-stop Boeing 737-700 (Scimitar Winglets) 7:40 Effective 2026-01-11 through 2026-01-16
Mon,Sun 08:05 Chicago Midway (MDW) 13:45 San Jose (SJC) B Southwest Airlines WN 2169 1-stop Boeing 737-700 (Scimitar Winglets) 7:40 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 08:05 Chicago Midway (MDW) 13:45 San Jose (SJC) B Southwest Airlines WN 2169 1-stop Boeing 737-700 (Scimitar Winglets) 7:40 Effective 2026-02-01 through 2026-02-06
Mon,Sun 08:05 Chicago Midway (MDW) 13:45 San Jose (SJC) B Southwest Airlines WN 2169 1-stop Boeing 737-700 (Scimitar Winglets) 7:40 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 08:05 Chicago Midway (MDW) 13:45 San Jose (SJC) B Southwest Airlines WN 2169 1-stop Boeing 737-700 (Scimitar Winglets) 7:40 Effective 2026-02-17 through 2026-02-23
Mon 08:05 Chicago Midway (MDW) 13:45 San Jose (SJC) B Southwest Airlines WN 2169 1-stop Boeing 737-700 (Scimitar Winglets) 7:40 Operates only on 2026-03-02
Mon 09:25 Chicago Midway (MDW) 13:55 San Jose (SJC) B Southwest Airlines WN 2323 1-stop Boeing 737-700 (Scimitar Winglets) 6:30 Operates only on 2026-01-05
Mon,Thu,Fri 10:10 Chicago Midway (MDW) 14:25 San Jose (SJC) B Southwest Airlines WN 2433 1-stop Boeing 737-700 (Scimitar Winglets) 6:15 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 06:15 Chicago Midway (MDW) 10:30 San Jose (SJC) B Southwest Airlines WN 2896 1-stop Boeing 737-700 (Scimitar Winglets) 6:15 Effective 2026-04-09 through 2026-06-01
Sun 06:30 Chicago Midway (MDW) 11:00 San Jose (SJC) B Southwest Airlines WN 3719 1-stop Boeing 737-700 (Scimitar Winglets) 6:30 Effective 2026-03-08 through 2026-04-05
Sun 10:00 Chicago Midway (MDW) 14:15 San Jose (SJC) B Southwest Airlines WN 3882 1-stop Boeing 737 MAX 8 (7M8) 6:15 Effective 2026-04-12 through 2026-05-17
Sun 10:00 Chicago Midway (MDW) 14:15 San Jose (SJC) B Southwest Airlines WN 3882 1-stop Boeing 737 MAX 8 (7M8) 6:15 Operates only on 2026-05-31
Sun 18:35 Chicago Midway (MDW) 22:55 San Jose (SJC) B Southwest Airlines WN 3884 1-stop Boeing 737-700 (Scimitar Winglets) 6:20 Effective 2026-04-12 through 2026-05-17
Sun 18:35 Chicago Midway (MDW) 22:55 San Jose (SJC) B Southwest Airlines WN 3884 1-stop Boeing 737-700 (Scimitar Winglets) 6:20 Operates only on 2026-05-31
Sat 16:05 Chicago Midway (MDW) 20:40 San Jose (SJC) B Southwest Airlines WN 3982 1-stop Boeing 737 MAX 8 (7M8) 6:35 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 10:15 Chicago Midway (MDW) 16:35 San Jose (SJC) B Southwest Airlines WN 423 2-stop Boeing 737-700 (Scimitar Winglets) 8:20 Effective 2026-03-05 through 2026-04-06
Sun 11:10 Chicago Midway (MDW) 17:20 San Jose (SJC) B Southwest Airlines WN 1541 2-stop Boeing 737-700 (Scimitar Winglets) 8:10 Operates only on 2026-05-24
Sat 10:10 Chicago Midway (MDW) 15:45 San Jose (SJC) B Southwest Airlines WN 2335 2-stop Boeing 737-700 (Scimitar Winglets) 7:35 Effective 2026-04-11 through 2026-05-30
Sat 12:20 Chicago Midway (MDW) 17:50 San Jose (SJC) B Southwest Airlines WN 2350 2-stop Boeing 737-700 (Scimitar Winglets) 7:30 Effective 2026-06-06 through 2026-08-01
Tue,Wed 10:05 Chicago Midway (MDW) 18:15 San Jose (SJC) B Southwest Airlines WN 4078 3-stop Boeing 737-700 (Scimitar Winglets) 10:10 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 07:55 Chicago Midway (MDW) 15:00 San Jose (SJC) B Southwest Airlines WN 4748 3-stop Boeing 737-700 (Scimitar Winglets) 9:05 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 07:55 Chicago Midway (MDW) 15:00 San Jose (SJC) B Southwest Airlines WN 4748 3-stop Boeing 737-700 (Scimitar Winglets) 9:05 Effective 2026-02-20 through 2026-03-01
Sat 10:15 Chicago Midway (MDW) 19:05 San Jose (SJC) B Southwest Airlines WN 1538 4-stop Boeing 737-700 (Scimitar Winglets) 10:50 Effective 2026-03-07 through 2026-04-04
Fri,Sun 07:50 Chicago Midway (MDW) 18:10 San Jose (SJC) B Southwest Airlines WN 1646 5-stop Boeing 737-700 (Scimitar Winglets) 12:20 Effective 2026-01-02 through 2026-01-04

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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.

Return (SJC-MDW) flights

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All airlines flying from Chicago Midway (MDW) to San Jose (SJC).

FLIGHT SCHEDULE

Non-Direct Flights:

Southwest Airlines WN864

17:00

Chicago Midway (MDW)

21:15

San Jose (SJC) B

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 6:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN864

17:00

Chicago Midway (MDW)

21:15

San Jose (SJC) B

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN864

17:00

Chicago Midway (MDW)

21:15

San Jose (SJC) B

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 6:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN864

17:00

Chicago Midway (MDW)

21:15

San Jose (SJC) B

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1181

07:15

Chicago Midway (MDW)

11:45

San Jose (SJC) B

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:30, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN1186

10:00

Chicago Midway (MDW)

14:25

San Jose (SJC) B

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1390

10:05

Chicago Midway (MDW)

14:15

San Jose (SJC) B

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2144

17:25

Chicago Midway (MDW)

22:50

San Jose (SJC) B

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 7:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2169

08:05

Chicago Midway (MDW)

13:45

San Jose (SJC) B

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 7:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2169

08:05

Chicago Midway (MDW)

13:45

San Jose (SJC) B

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2169

08:05

Chicago Midway (MDW)

13:45

San Jose (SJC) B

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 7:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2169

08:05

Chicago Midway (MDW)

13:45

San Jose (SJC) B

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2169

08:05

Chicago Midway (MDW)

13:45

San Jose (SJC) B

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 7:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2169

08:05

Chicago Midway (MDW)

13:45

San Jose (SJC) B

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 7:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2323

09:25

Chicago Midway (MDW)

13:55

San Jose (SJC) B

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2433

10:10

Chicago Midway (MDW)

14:25

San Jose (SJC) B

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2896

06:15

Chicago Midway (MDW)

10:30

San Jose (SJC) B

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3719

06:30

Chicago Midway (MDW)

11:00

San Jose (SJC) B

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3882

10:00

Chicago Midway (MDW)

14:15

San Jose (SJC) B

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3882

10:00

Chicago Midway (MDW)

14:15

San Jose (SJC) B

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3884

18:35

Chicago Midway (MDW)

22:55

San Jose (SJC) B

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3884

18:35

Chicago Midway (MDW)

22:55

San Jose (SJC) B

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3982

16:05

Chicago Midway (MDW)

20:40

San Jose (SJC) B

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:35, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN423

10:15

Chicago Midway (MDW)

16:35

San Jose (SJC) B

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 8:20, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1541

11:10

Chicago Midway (MDW)

17:20

San Jose (SJC) B

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 8:10, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2335

10:10

Chicago Midway (MDW)

15:45

San Jose (SJC) B

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 7:35, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2350

12:20

Chicago Midway (MDW)

17:50

San Jose (SJC) B

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 7:30, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4078

10:05

Chicago Midway (MDW)

18:15

San Jose (SJC) B

Effective 2026-03-10 through 2026-04-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 10:10, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4748

07:55

Chicago Midway (MDW)

15:00

San Jose (SJC) B

Effective 2026-02-12 through 2026-02-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 9:05, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4748

07:55

Chicago Midway (MDW)

15:00

San Jose (SJC) B

Effective 2026-02-20 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 9:05, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1538

10:15

Chicago Midway (MDW)

19:05

San Jose (SJC) B

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 10:50, 4-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1646

07:50

Chicago Midway (MDW)

18:10

San Jose (SJC) B

Effective 2026-01-02 through 2026-01-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 12:20, 5-stop
Boeing 737-700 (Scimitar Winglets)

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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.

Return (SJC-MDW) flights

Feedback - Disclaimer - Privacy