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

FLIGHT SCHEDULE
Direct Flights:
Sat 07:15 San Diego (SAN) 1 13:15 Chicago Midway (MDW) Southwest Airlines WN 3402 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-02-14 through 2026-02-28
Sat 10:35 San Diego (SAN) 1 16:30 Chicago Midway (MDW) Southwest Airlines WN 3403 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-01-10 through 2026-02-07
Sat 11:20 San Diego (SAN) 1 17:15 Chicago Midway (MDW) Southwest Airlines WN 3403 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-02-14 through 2026-02-28
Mon,Thu,Fri 12:20 San Diego (SAN) 1 18:20 Chicago Midway (MDW) Southwest Airlines WN 3403 Non-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 12:20 San Diego (SAN) 1 18:20 Chicago Midway (MDW) Southwest Airlines WN 3403 Non-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-02-20 through 2026-03-01
Sat 17:55 San Diego (SAN) 1 23:45 Chicago Midway (MDW) Southwest Airlines WN 3404 Non-stop Boeing 737 MAX 8 (7M8) 3:50 Effective 2026-02-14 through 2026-02-28
Mon,Thu,Fri 18:45 San Diego (SAN) 1 00:35 Chicago Midway (MDW) Southwest Airlines WN 3404 Non-stop Boeing 737 MAX 8 (7M8) 3:50 Effective 2026-02-12 through 2026-02-16 The flight arrives 1 day after departure.
Thu,Fri,Sun 18:45 San Diego (SAN) 1 00:35 Chicago Midway (MDW) Southwest Airlines WN 3404 Non-stop Boeing 737 MAX 8 (7M8) 3:50 Effective 2026-02-20 through 2026-03-01 The flight arrives 1 day after departure.
Sun 06:25 San Diego (SAN) 1 12:25 Chicago Midway (MDW) Southwest Airlines WN 3430 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-08-09 through 2026-09-27
Sat 06:35 San Diego (SAN) 1 12:35 Chicago Midway (MDW) Southwest Airlines WN 3430 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-08-08 through 2026-09-26
Tue,Wed 06:55 San Diego (SAN) 1 12:55 Chicago Midway (MDW) Southwest Airlines WN 3430 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-08-04 through 2026-09-30
Daily 22:40 San Diego (SAN) 1 04:30 Chicago Midway (MDW) Southwest Airlines WN 3431 Non-stop Boeing 737-700 (Scimitar Winglets) 3:50 Effective 2026-08-04 through 2026-09-30 The flight arrives 1 day after departure.
Sun 15:40 San Diego (SAN) 1 21:35 Chicago Midway (MDW) Southwest Airlines WN 3448 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 17:30 San Diego (SAN) 1 23:25 Chicago Midway (MDW) Southwest Airlines WN 3448 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-06-04 through 2026-08-03
Sun 06:20 San Diego (SAN) 1 12:25 Chicago Midway (MDW) Southwest Airlines WN 3513 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-06-07 through 2026-08-02
Tue,Wed 06:20 San Diego (SAN) 1 12:25 Chicago Midway (MDW) Southwest Airlines WN 3513 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-06-09 through 2026-07-29
Mon,Thu-Sat 06:30 San Diego (SAN) 1 12:35 Chicago Midway (MDW) Southwest Airlines WN 3513 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-06-04 through 2026-08-03
Mon 12:20 San Diego (SAN) 1 18:25 Chicago Midway (MDW) Southwest Airlines WN 3683 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2026-01-05
Wed,Thu 17:00 San Diego (SAN) 1 22:55 Chicago Midway (MDW) Southwest Airlines WN 3683 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Valid until 2026-01-01
Mon 06:35 San Diego (SAN) 1 12:40 Chicago Midway (MDW) Southwest Airlines WN 3768 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2026-01-05
Wed,Thu 11:00 San Diego (SAN) 1 17:00 Chicago Midway (MDW) Southwest Airlines WN 3768 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Valid until 2026-01-01
Sat 11:45 San Diego (SAN) 1 17:40 Chicago Midway (MDW) Southwest Airlines WN 3910 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 12:05 San Diego (SAN) 1 18:00 Chicago Midway (MDW) Southwest Airlines WN 3910 Non-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-03-05 through 2026-04-06
Tue,Wed 08:30 San Diego (SAN) 1 14:30 Chicago Midway (MDW) Southwest Airlines WN 4025 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-04-07 through 2026-06-03
Sat 08:55 San Diego (SAN) 1 14:50 Chicago Midway (MDW) Southwest Airlines WN 4025 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-04-11 through 2026-05-30
Sun 10:55 San Diego (SAN) 1 16:55 Chicago Midway (MDW) Southwest Airlines WN 4025 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Operates only on 2026-05-24
Sun 11:40 San Diego (SAN) 1 17:40 Chicago Midway (MDW) Southwest Airlines WN 4025 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-04-12 through 2026-05-17
Sun 11:40 San Diego (SAN) 1 17:40 Chicago Midway (MDW) Southwest Airlines WN 4025 Non-stop Boeing 737-800 (73H) 4:00 Operates only on 2026-05-31
Mon,Thu,Fri 11:50 San Diego (SAN) 1 17:50 Chicago Midway (MDW) Southwest Airlines WN 4025 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-04-09 through 2026-06-01
Daily 22:40 San Diego (SAN) 1 04:35 Chicago Midway (MDW) Southwest Airlines WN 4094 Non-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-04-07 through 2026-06-03 The flight arrives 1 day after departure.
Tue,Wed 10:50 San Diego (SAN) 1 16:50 Chicago Midway (MDW) Southwest Airlines WN 4163 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 12:10 San Diego (SAN) 1 18:10 Chicago Midway (MDW) Southwest Airlines WN 4163 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-06-04 through 2026-08-03
Tue,Wed 10:50 San Diego (SAN) 1 16:45 Chicago Midway (MDW) Southwest Airlines WN 4363 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 16:45 San Diego (SAN) 1 22:35 Chicago Midway (MDW) Southwest Airlines WN 4363 Non-stop Boeing 737-800 (73H) 3:50 Effective 2026-03-05 through 2026-04-06
Sat 10:00 San Diego (SAN) 1 16:00 Chicago Midway (MDW) Southwest Airlines WN 4443 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-08-08 through 2026-09-26
Tue,Wed 11:10 San Diego (SAN) 1 17:05 Chicago Midway (MDW) Southwest Airlines WN 4443 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 17:50 San Diego (SAN) 1 23:45 Chicago Midway (MDW) Southwest Airlines WN 4443 Non-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-08-06 through 2026-09-28
Wed,Thu 06:30 San Diego (SAN) 1 12:35 Chicago Midway (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Valid until 2026-01-01
Sat 18:45 San Diego (SAN) 1 00:40 Chicago Midway (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737-800 (73H) 3:55 Valid until 2026-01-03 The flight arrives 1 day after departure.
Mon,Tue,Fri,Sun 19:00 San Diego (SAN) 1 00:55 Chicago Midway (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Valid until 2026-01-04 The flight arrives 1 day after departure.
Mon 19:35 San Diego (SAN) 1 01:30 Chicago Midway (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737-800 (73H) 3:55 Operates only on 2026-01-05 The flight arrives 1 day after departure.
Non-Direct Flights:
Sun 12:20 San Diego (SAN) 1 20:05 Chicago Midway (MDW) Southwest Airlines WN 105 1-stop Boeing 737-800 (73H) 5:45 Operates only on 2026-05-24
Tue,Wed 11:45 San Diego (SAN) 1 21:35 Chicago Midway (MDW) Southwest Airlines WN 999 1-stop Boeing 737-800 (73H) 7:50 Effective 2026-06-09 through 2026-07-29
Sat 08:30 San Diego (SAN) 1 16:45 Chicago Midway (MDW) Southwest Airlines WN 1201 1-stop Boeing 737-800 (73H) 6:15 Effective 2026-06-06 through 2026-08-01
Mon 11:10 San Diego (SAN) 1 18:30 Chicago Midway (MDW) Southwest Airlines WN 2082 1-stop Boeing 737-700 (Scimitar Winglets) 5:20 Operates only on 2026-01-05
Mon,Thu,Fri 17:10 San Diego (SAN) 1 00:35 Chicago Midway (MDW) Southwest Airlines WN 2521 1-stop Boeing 737 MAX 8 (7M8) 5:25 Effective 2026-06-04 through 2026-08-03 The flight arrives 1 day after departure.
Sat 06:25 San Diego (SAN) 1 14:20 Chicago Midway (MDW) Southwest Airlines WN 4061 1-stop Boeing 737 MAX 8 (7M8) 5:55 Effective 2026-04-11 through 2026-05-30
Sun 08:45 San Diego (SAN) 1 18:00 Chicago Midway (MDW) Southwest Airlines WN 1538 2-stop Boeing 737-700 (Scimitar Winglets) 7:15 Effective 2026-04-12 through 2026-05-17
Sun 08:45 San Diego (SAN) 1 18:00 Chicago Midway (MDW) Southwest Airlines WN 1538 2-stop Boeing 737-700 (Scimitar Winglets) 7:15 Operates only on 2026-05-31
Fri,Sun 11:30 San Diego (SAN) 1 21:25 Chicago Midway (MDW) Southwest Airlines WN 2373 2-stop Boeing 737-700 (Scimitar Winglets) 7:55 Effective 2026-01-02 through 2026-01-04

1 2 3

A domestic route departing from the San Diego airport (SAN) and arriving at Chicago Midway airport (MDW).
The flight distance is 1724 miles, or 2774 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 3:50 and 4:05.

Return (MDW-SAN) flights

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN3402

07:15

San Diego (SAN) 1

13:15

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3403

10:35

San Diego (SAN) 1

16:30

Chicago Midway (MDW)

Effective 2026-01-10 through 2026-02-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3403

11:20

San Diego (SAN) 1

17:15

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3403

12:20

San Diego (SAN) 1

18:20

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3403

12:20

San Diego (SAN) 1

18:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3404

17:55

San Diego (SAN) 1

23:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3404

18:45

San Diego (SAN) 1

00:35(+1)

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:50, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3404

18:45

San Diego (SAN) 1

00:35(+1)

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 3:50, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3430

06:25

San Diego (SAN) 1

12:25

Chicago Midway (MDW)

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3430

06:35

San Diego (SAN) 1

12:35

Chicago Midway (MDW)

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3430

06:55

San Diego (SAN) 1

12:55

Chicago Midway (MDW)

Effective 2026-08-04 through 2026-09-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3431

22:40

San Diego (SAN) 1

04:30(+1)

Chicago Midway (MDW)

Effective 2026-08-04 through 2026-09-30

Mon

Tue

Wed

Thu

Fri

Sat

Sun

Duration: 3:50, non-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3448

15:40

San Diego (SAN) 1

21:35

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3448

17:30

San Diego (SAN) 1

23:25

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3513

06:20

San Diego (SAN) 1

12:25

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3513

06:20

San Diego (SAN) 1

12:25

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:05, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3513

06:30

San Diego (SAN) 1

12:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat

Sun
-

Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3683

12:20

San Diego (SAN) 1

18:25

Chicago Midway (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3683

17:00

San Diego (SAN) 1

22:55

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3768

06:35

San Diego (SAN) 1

12:40

Chicago Midway (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:05, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3768

11:00

San Diego (SAN) 1

17:00

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3910

11:45

San Diego (SAN) 1

17:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3910

12:05

San Diego (SAN) 1

18:00

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4025

08:30

San Diego (SAN) 1

14:30

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4025

08:55

San Diego (SAN) 1

14:50

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4025

10:55

San Diego (SAN) 1

16:55

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4025

11:40

San Diego (SAN) 1

17:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4025

11:40

San Diego (SAN) 1

17:40

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4025

11:50

San Diego (SAN) 1

17:50

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4094

22:40

San Diego (SAN) 1

04:35(+1)

Chicago Midway (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat

Sun

Duration: 3:55, non-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN4163

10:50

San Diego (SAN) 1

16:50

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4163

12:10

San Diego (SAN) 1

18:10

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4363

10:50

San Diego (SAN) 1

16:45

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4363

16:45

San Diego (SAN) 1

22:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4443

10:00

San Diego (SAN) 1

16:00

Chicago Midway (MDW)

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4443

11:10

San Diego (SAN) 1

17:05

Chicago Midway (MDW)

Effective 2026-08-04 through 2026-09-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4443

17:50

San Diego (SAN) 1

23:45

Chicago Midway (MDW)

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4602

06:30

San Diego (SAN) 1

12:35

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4602

18:45

San Diego (SAN) 1

00:40(+1)

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN4602

19:00

San Diego (SAN) 1

00:55(+1)

Chicago Midway (MDW)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN4602

19:35

San Diego (SAN) 1

01:30(+1)

Chicago Midway (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Non-Direct Flights:

Southwest Airlines WN105

12:20

San Diego (SAN) 1

20:05

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:45, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN999

11:45

San Diego (SAN) 1

21:35

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 7:50, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN1201

08:30

San Diego (SAN) 1

16:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:15, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN2082

11:10

San Diego (SAN) 1

18:30

Chicago Midway (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2521

17:10

San Diego (SAN) 1

00:35(+1)

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 5:25, 1-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Non-Direct Flights:

Southwest Airlines WN4061

06:25

San Diego (SAN) 1

14:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN1538

08:45

San Diego (SAN) 1

18:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:15, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1538

08:45

San Diego (SAN) 1

18:00

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:15, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2373

11:30

San Diego (SAN) 1

21:25

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 7:55, 2-stop
Boeing 737-700 (Scimitar Winglets)

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A domestic route departing from the San Diego airport (SAN) and arriving at Chicago Midway airport (MDW).
The flight distance is 1724 miles, or 2774 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 3:50 and 4:05.

Return (MDW-SAN) flights

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