All airlines flying from Chicago Midway (MDW) to San Diego (SAN).

FLIGHT SCHEDULE
Non-Direct Flights:
Mon,Thu,Fri 07:30 Chicago Midway (MDW) 11:15 San Diego (SAN) 1 Southwest Airlines WN 347 1-stop Boeing 737 MAX 8 (7M8) 5:45 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 15:30 Chicago Midway (MDW) 20:40 San Diego (SAN) 1 Southwest Airlines WN 878 1-stop Boeing 737-700 (Scimitar Winglets) 7:10 Effective 2026-03-05 through 2026-04-06
Mon 07:50 Chicago Midway (MDW) 11:30 San Diego (SAN) 1 Southwest Airlines WN 973 1-stop Boeing 737-700 (Scimitar Winglets) 5:40 Operates only on 2026-01-05
Mon,Thu,Fri 11:00 Chicago Midway (MDW) 15:30 San Diego (SAN) 1 Southwest Airlines WN 1139 1-stop Boeing 737 MAX 8 (7M8) 6:30 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 07:55 Chicago Midway (MDW) 13:00 San Diego (SAN) 1 Southwest Airlines WN 1369 1-stop Boeing 737 MAX 8 (7M8) 7:05 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 07:55 Chicago Midway (MDW) 13:00 San Diego (SAN) 1 Southwest Airlines WN 1369 1-stop Boeing 737 MAX 8 (7M8) 7:05 Effective 2026-02-20 through 2026-03-01
Thu 17:15 Chicago Midway (MDW) 21:10 San Diego (SAN) 1 Southwest Airlines WN 1714 1-stop Boeing 737 MAX 8 (7M8) 5:55 Valid until 2026-01-01
Thu,Fri,Sun 08:05 Chicago Midway (MDW) 12:50 San Diego (SAN) 1 Southwest Airlines WN 2553 1-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2026-01-11 through 2026-01-16
Mon,Sun 08:05 Chicago Midway (MDW) 12:50 San Diego (SAN) 1 Southwest Airlines WN 2553 1-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 08:05 Chicago Midway (MDW) 12:50 San Diego (SAN) 1 Southwest Airlines WN 2553 1-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2026-02-01 through 2026-02-06
Mon,Sun 08:05 Chicago Midway (MDW) 12:50 San Diego (SAN) 1 Southwest Airlines WN 2553 1-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 08:05 Chicago Midway (MDW) 12:50 San Diego (SAN) 1 Southwest Airlines WN 2553 1-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2026-02-17 through 2026-02-23
Mon 08:05 Chicago Midway (MDW) 12:50 San Diego (SAN) 1 Southwest Airlines WN 2553 1-stop Boeing 737-700 (Scimitar Winglets) 6:45 Operates only on 2026-03-02
Sat 12:10 Chicago Midway (MDW) 16:15 San Diego (SAN) 1 Southwest Airlines WN 2721 1-stop Boeing 737 MAX 8 (7M8) 6:05 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 10:05 Chicago Midway (MDW) 15:30 San Diego (SAN) 1 Southwest Airlines WN 2809 1-stop Boeing 737 MAX 8 (7M8) 7:25 Effective 2026-06-04 through 2026-08-03
Tue,Wed 10:15 Chicago Midway (MDW) 15:40 San Diego (SAN) 1 Southwest Airlines WN 2809 1-stop Boeing 737 MAX 8 (7M8) 7:25 Effective 2026-06-09 through 2026-07-29
Sat 12:30 Chicago Midway (MDW) 17:00 San Diego (SAN) 1 Southwest Airlines WN 2876 1-stop Boeing 737 MAX 8 (7M8) 6:30 Effective 2026-06-06 through 2026-08-01
Sat 19:00 Chicago Midway (MDW) 23:25 San Diego (SAN) 1 Southwest Airlines WN 3102 1-stop Boeing 737-800 (73H) 6:25 Effective 2026-03-07 through 2026-04-04
Sun 17:35 Chicago Midway (MDW) 21:15 San Diego (SAN) 1 Southwest Airlines WN 3345 1-stop Boeing 737-700 (Scimitar Winglets) 5:40 Effective 2026-06-07 through 2026-08-02
Tue,Wed 07:30 Chicago Midway (MDW) 11:20 San Diego (SAN) 1 Southwest Airlines WN 3465 1-stop Boeing 737 MAX 8 (7M8) 5:50 Effective 2026-04-07 through 2026-06-03
Mon,Tue,Fri,Sun 11:35 Chicago Midway (MDW) 15:10 San Diego (SAN) 1 Southwest Airlines WN 4016 1-stop Boeing 737 MAX 8 (7M8) 5:35 Valid until 2026-01-04
Mon,Thu,Fri 11:30 Chicago Midway (MDW) 15:25 San Diego (SAN) 1 Southwest Airlines WN 4346 1-stop Boeing 737 MAX 8 (7M8) 5:55 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 11:30 Chicago Midway (MDW) 15:25 San Diego (SAN) 1 Southwest Airlines WN 4346 1-stop Boeing 737 MAX 8 (7M8) 5:55 Effective 2026-02-20 through 2026-03-01
Mon,Thu,Fri 16:55 Chicago Midway (MDW) 23:25 San Diego (SAN) 1 Southwest Airlines WN 4487 1-stop Boeing 737 MAX 8 (7M8) 8:30 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 16:55 Chicago Midway (MDW) 23:25 San Diego (SAN) 1 Southwest Airlines WN 4487 1-stop Boeing 737 MAX 8 (7M8) 8:30 Effective 2026-02-20 through 2026-03-01
Sat 10:15 Chicago Midway (MDW) 13:30 San Diego (SAN) 1 Southwest Airlines WN 4905 1-stop Boeing 737-800 (73H) 5:15 Effective 2026-06-06 through 2026-08-01
Tue,Wed 08:10 Chicago Midway (MDW) 15:05 San Diego (SAN) 1 Southwest Airlines WN 533 2-stop Boeing 737-700 (Scimitar Winglets) 8:55 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 10:10 Chicago Midway (MDW) 15:05 San Diego (SAN) 1 Southwest Airlines WN 1771 2-stop Boeing 737-700 (Scimitar Winglets) 6:55 Effective 2026-06-04 through 2026-08-03
Sun 10:10 Chicago Midway (MDW) 15:15 San Diego (SAN) 1 Southwest Airlines WN 2104 2-stop Boeing 737-700 (Scimitar Winglets) 7:05 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 16:05 Chicago Midway (MDW) 21:25 San Diego (SAN) 1 Southwest Airlines WN 2329 2-stop Boeing 737-700 (Scimitar Winglets) 7:20 Effective 2026-04-09 through 2026-06-01
Tue,Wed 10:10 Chicago Midway (MDW) 15:45 San Diego (SAN) 1 Southwest Airlines WN 2335 2-stop Boeing 737-700 (Scimitar Winglets) 7:35 Effective 2026-04-07 through 2026-06-03
Sat 11:20 Chicago Midway (MDW) 17:05 San Diego (SAN) 1 Southwest Airlines WN 2340 2-stop Boeing 737-700 (Scimitar Winglets) 7:45 Effective 2026-02-14 through 2026-02-28
Mon,Thu,Fri 11:00 Chicago Midway (MDW) 18:30 San Diego (SAN) 1 Southwest Airlines WN 2761 2-stop Boeing 737 MAX 8 (7M8) 9:30 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 11:00 Chicago Midway (MDW) 18:30 San Diego (SAN) 1 Southwest Airlines WN 2761 2-stop Boeing 737 MAX 8 (7M8) 9:30 Effective 2026-02-20 through 2026-03-01
Tue,Wed 13:05 Chicago Midway (MDW) 19:35 San Diego (SAN) 1 Southwest Airlines WN 2808 2-stop Boeing 737 MAX 8 (7M8) 8:30 Effective 2026-03-10 through 2026-04-01
Tue,Wed 06:00 Chicago Midway (MDW) 12:00 San Diego (SAN) 1 Southwest Airlines WN 3184 2-stop Boeing 737-800 (73H) 8:00 Effective 2026-03-10 through 2026-04-01
Sun 10:05 Chicago Midway (MDW) 15:05 San Diego (SAN) 1 Southwest Airlines WN 4248 2-stop Boeing 737-700 (Scimitar Winglets) 7:00 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 12:50 Chicago Midway (MDW) 21:35 San Diego (SAN) 1 Southwest Airlines WN 2837 4-stop Boeing 737-700 (Scimitar Winglets) 10:45 Effective 2026-03-05 through 2026-04-06

1 2 3

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.

Return (SAN-MDW) flights

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All airlines flying from Chicago Midway (MDW) to San Diego (SAN).

FLIGHT SCHEDULE

Non-Direct Flights:

Southwest Airlines WN347

07:30

Chicago Midway (MDW)

11:15

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 5:45, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN878

15:30

Chicago Midway (MDW)

20:40

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 7:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN973

07:50

Chicago Midway (MDW)

11:30

San Diego (SAN) 1

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1139

11:00

Chicago Midway (MDW)

15:30

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:30, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1369

07:55

Chicago Midway (MDW)

13:00

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 7:05, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1369

07:55

Chicago Midway (MDW)

13:00

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 7:05, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1714

17:15

Chicago Midway (MDW)

21:10

San Diego (SAN) 1

Valid until 2026-01-01

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 5:55, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2553

08:05

Chicago Midway (MDW)

12:50

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 6:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2553

08:05

Chicago Midway (MDW)

12:50

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2553

08:05

Chicago Midway (MDW)

12:50

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 6:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2553

08:05

Chicago Midway (MDW)

12:50

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2553

08:05

Chicago Midway (MDW)

12:50

San Diego (SAN) 1

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

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 6:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2553

08:05

Chicago Midway (MDW)

12:50

San Diego (SAN) 1

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2721

12:10

Chicago Midway (MDW)

16:15

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:05, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2809

10:05

Chicago Midway (MDW)

15:30

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN2809

10:15

Chicago Midway (MDW)

15:40

San Diego (SAN) 1

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN2876

12:30

Chicago Midway (MDW)

17:00

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:30, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3102

19:00

Chicago Midway (MDW)

23:25

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:25, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN3345

17:35

Chicago Midway (MDW)

21:15

San Diego (SAN) 1

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3465

07:30

Chicago Midway (MDW)

11:20

San Diego (SAN) 1

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:50, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4016

11:35

Chicago Midway (MDW)

15:10

San Diego (SAN) 1

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 5:35, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4346

11:30

Chicago Midway (MDW)

15:25

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 5:55, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4346

11:30

Chicago Midway (MDW)

15:25

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 5:55, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4487

16:55

Chicago Midway (MDW)

23:25

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 8:30, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4487

16:55

Chicago Midway (MDW)

23:25

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 8:30, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4905

10:15

Chicago Midway (MDW)

13:30

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:15, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN533

08:10

Chicago Midway (MDW)

15:05

San Diego (SAN) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 8:55, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1771

10:10

Chicago Midway (MDW)

15:05

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:55, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2104

10:10

Chicago Midway (MDW)

15:15

San Diego (SAN) 1

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2329

16:05

Chicago Midway (MDW)

21:25

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 7:20, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2335

10:10

Chicago Midway (MDW)

15:45

San Diego (SAN) 1

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN2340

11:20

Chicago Midway (MDW)

17:05

San Diego (SAN) 1

Effective 2026-02-14 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 7:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2761

11:00

Chicago Midway (MDW)

18:30

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 9:30, 2-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2761

11:00

Chicago Midway (MDW)

18:30

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 9:30, 2-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2808

13:05

Chicago Midway (MDW)

19:35

San Diego (SAN) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 8:30, 2-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3184

06:00

Chicago Midway (MDW)

12:00

San Diego (SAN) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 8:00, 2-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN4248

10:05

Chicago Midway (MDW)

15:05

San Diego (SAN) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:00, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2837

12:50

Chicago Midway (MDW)

21:35

San Diego (SAN) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 10:45, 4-stop
Boeing 737-700 (Scimitar Winglets)

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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.

Return (SAN-MDW) flights

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