Southwest Airlines flights from San Diego (SAN) to Midway, Chicago (MDW).

FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri,Sun 06:55 San Diego (SAN) 1 12:55 Midway, Chicago (MDW) Southwest Airlines WN 202 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-08-07 through 2025-08-29
Sun 06:55 San Diego (SAN) 1 12:55 Midway, Chicago (MDW) Southwest Airlines WN 202 Non-stop Boeing 737-700 (73W) 4:00 Operates only on 2025-08-31
Mon,Thu,Fri,Sun 06:55 San Diego (SAN) 1 12:55 Midway, Chicago (MDW) Southwest Airlines WN 202 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-09-01 through 2025-09-29
Tue,Wed 10:40 San Diego (SAN) 1 16:40 Midway, Chicago (MDW) Southwest Airlines WN 202 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-08-05 through 2025-10-01
Fri 16:00 San Diego (SAN) 1 22:00 Midway, Chicago (MDW) Southwest Airlines WN 205 Non-stop Boeing 737-700 (73W) 4:00 Operates only on 2025-07-04
Sat 07:55 San Diego (SAN) 1 13:50 Midway, Chicago (MDW) Southwest Airlines WN 233 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Valid until 2025-05-31
Sat 10:45 San Diego (SAN) 1 16:45 Midway, Chicago (MDW) Southwest Airlines WN 457 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-08-09 through 2025-09-27
Sun 13:50 San Diego (SAN) 1 19:50 Midway, Chicago (MDW) Southwest Airlines WN 457 Non-stop Boeing 737-700 (73W) 4:00 Effective 2025-08-10 through 2025-08-24
Sun 13:50 San Diego (SAN) 1 19:50 Midway, Chicago (MDW) Southwest Airlines WN 457 Non-stop Boeing 737-700 (73W) 4:00 Effective 2025-09-07 through 2025-09-28
Sun 15:35 San Diego (SAN) 1 21:30 Midway, Chicago (MDW) Southwest Airlines WN 457 Non-stop Boeing 737-700 (73W) 3:55 Operates only on 2025-08-31
Tue,Wed 16:05 San Diego (SAN) 1 22:00 Midway, Chicago (MDW) Southwest Airlines WN 457 Non-stop Boeing 737-700 (73W) 3:55 Effective 2025-08-05 through 2025-10-01
Sat 16:50 San Diego (SAN) 1 22:50 Midway, Chicago (MDW) Southwest Airlines WN 478 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-10-04 through 2025-11-01
Sun 18:45 San Diego (SAN) 1 00:45 Midway, Chicago (MDW) Southwest Airlines WN 478 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-10-05 through 2025-10-26 The flight arrives 1 day after departure.
Mon-Fri 17:55 San Diego (SAN) 1 23:55 Midway, Chicago (MDW) Southwest Airlines WN 495 Non-stop Boeing 737-700 (73W) 4:00 Valid until 2025-06-04
Fri 10:35 San Diego (SAN) 1 16:35 Midway, Chicago (MDW) Southwest Airlines WN 557 Non-stop Boeing 737-800 (73H) 4:00 Operates only on 2025-07-04
Mon,Thu,Fri 11:25 San Diego (SAN) 1 17:25 Midway, Chicago (MDW) Southwest Airlines WN 557 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 11:25 San Diego (SAN) 1 17:25 Midway, Chicago (MDW) Southwest Airlines WN 557 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-07-07 through 2025-08-04
Sat 07:30 San Diego (SAN) 1 13:30 Midway, Chicago (MDW) Southwest Airlines WN 594 Non-stop Boeing 737-700 (73W) 4:00 Effective 2025-08-09 through 2025-09-27
Tue,Wed 08:10 San Diego (SAN) 1 14:10 Midway, Chicago (MDW) Southwest Airlines WN 594 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-08-05 through 2025-10-01
Tue,Wed 18:25 San Diego (SAN) 1 00:25 Midway, Chicago (MDW) Southwest Airlines WN 925 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-10-07 through 2025-10-29 The flight arrives 1 day after departure.
Mon,Thu,Fri 06:30 San Diego (SAN) 1 12:30 Midway, Chicago (MDW) Southwest Airlines WN 1169 Non-stop Boeing 737-700 (73W) 4:00 Valid until 2025-06-02
Tue,Wed 07:35 San Diego (SAN) 1 13:30 Midway, Chicago (MDW) Southwest Airlines WN 1428 Non-stop Boeing 737-700 (73W) 3:55 Valid until 2025-06-04
Mon,Thu,Fri 11:15 San Diego (SAN) 1 17:15 Midway, Chicago (MDW) Southwest Airlines WN 1428 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Valid until 2025-06-02
Sat 11:15 San Diego (SAN) 1 17:15 Midway, Chicago (MDW) Southwest Airlines WN 1428 Non-stop Boeing 737-800 (73H) 4:00 Valid until 2025-05-31
Sun 13:50 San Diego (SAN) 1 19:50 Midway, Chicago (MDW) Southwest Airlines WN 1428 Non-stop Boeing 737-700 (73W) 4:00 Operates only on 2025-05-04
Sun 13:50 San Diego (SAN) 1 19:50 Midway, Chicago (MDW) Southwest Airlines WN 1428 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-05-11 through 2025-05-18
Sun 13:50 San Diego (SAN) 1 19:50 Midway, Chicago (MDW) Southwest Airlines WN 1428 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Operates only on 2025-06-01
Thu 12:05 San Diego (SAN) 1 18:10 Midway, Chicago (MDW) Southwest Airlines WN 1696 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2025-11-27
Sun 10:50 San Diego (SAN) 1 16:50 Midway, Chicago (MDW) Southwest Airlines WN 1697 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Operates only on 2025-08-31
Sun 11:00 San Diego (SAN) 1 17:00 Midway, Chicago (MDW) Southwest Airlines WN 1697 Non-stop Boeing 737-700 (73W) 4:00 Effective 2025-08-10 through 2025-08-24
Sun 11:00 San Diego (SAN) 1 17:00 Midway, Chicago (MDW) Southwest Airlines WN 1697 Non-stop Boeing 737-700 (73W) 4:00 Effective 2025-09-07 through 2025-09-28
Mon-Wed 12:55 San Diego (SAN) 1 18:55 Midway, Chicago (MDW) Southwest Airlines WN 1748 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 12:55 San Diego (SAN) 1 18:55 Midway, Chicago (MDW) Southwest Airlines WN 1748 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-12-19 through 2026-01-04
Sat 13:30 San Diego (SAN) 1 19:30 Midway, Chicago (MDW) Southwest Airlines WN 1748 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-11-22 through 2025-11-29
Sat 13:30 San Diego (SAN) 1 19:30 Midway, Chicago (MDW) Southwest Airlines WN 1748 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-12-20 through 2026-01-03
Thu 06:40 San Diego (SAN) 1 12:45 Midway, Chicago (MDW) Southwest Airlines WN 1887 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2025-11-27
Tue,Wed 11:00 San Diego (SAN) 1 17:10 Midway, Chicago (MDW) Southwest Airlines WN 1981 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2025-10-07 through 2025-10-29
Mon,Thu,Fri 18:30 San Diego (SAN) 1 00:30 Midway, Chicago (MDW) Southwest Airlines WN 2053 Non-stop Boeing 737-700 (73W) 4:00 Effective 2025-08-07 through 2025-09-29 The flight arrives 1 day after departure.
Sun 13:20 San Diego (SAN) 1 19:25 Midway, Chicago (MDW) Southwest Airlines WN 2139 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-10-05 through 2025-10-26
Mon-Wed 06:35 San Diego (SAN) 1 12:40 Midway, Chicago (MDW) Southwest Airlines WN 2153 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 06:35 San Diego (SAN) 1 12:40 Midway, Chicago (MDW) Southwest Airlines WN 2153 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-12-19 through 2026-01-04
Sat 07:10 San Diego (SAN) 1 13:10 Midway, Chicago (MDW) Southwest Airlines WN 2153 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-11-22 through 2025-11-29
Sat 07:10 San Diego (SAN) 1 13:10 Midway, Chicago (MDW) Southwest Airlines WN 2153 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-12-20 through 2026-01-03
Tue,Wed 14:15 San Diego (SAN) 1 20:10 Midway, Chicago (MDW) Southwest Airlines WN 2189 Non-stop Boeing 737-700 (73W) 3:55 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 13:40 San Diego (SAN) 1 19:40 Midway, Chicago (MDW) Southwest Airlines WN 2206 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-08-07 through 2025-09-29
Mon,Thu,Fri 12:05 San Diego (SAN) 1 18:10 Midway, Chicago (MDW) Southwest Airlines WN 2872 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-10-02 through 2025-10-31
Sun 19:55 San Diego (SAN) 1 01:50 Midway, Chicago (MDW) Southwest Airlines WN 2876 Non-stop Boeing 737-800 (73H) 3:55 Valid until 2025-05-18 The flight arrives 1 day after departure.
Sun 19:55 San Diego (SAN) 1 01:50 Midway, Chicago (MDW) Southwest Airlines WN 2876 Non-stop Boeing 737-800 (73H) 3:55 Operates only on 2025-06-01 The flight arrives 1 day after departure.
Sun 11:55 San Diego (SAN) 1 18:00 Midway, Chicago (MDW) Southwest Airlines WN 2921 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-06-08 through 2025-08-03
Sat 07:20 San Diego (SAN) 1 13:25 Midway, Chicago (MDW) Southwest Airlines WN 2927 Non-stop Boeing 737-700 (73W) 4:05 Effective 2025-06-07 through 2025-08-02

1 2 3

A domestic route departing from the San Diego airport (SAN) and arriving at Midway, Chicago 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 3:55 and 4:10.

Feedback - Disclaimer - Privacy

Southwest Airlines flights from San Diego (SAN) to Midway, Chicago (MDW).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN202

06:55

San Diego (SAN) 1

12:55

Midway, Chicago (MDW)

Effective 2025-08-07 through 2025-08-29

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Southwest Airlines WN202

06:55

San Diego (SAN) 1

12:55

Midway, Chicago (MDW)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN202

06:55

San Diego (SAN) 1

12:55

Midway, Chicago (MDW)

Effective 2025-09-01 through 2025-09-29

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Southwest Airlines WN202

10:40

San Diego (SAN) 1

16:40

Midway, Chicago (MDW)

Effective 2025-08-05 through 2025-10-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN205

16:00

San Diego (SAN) 1

22:00

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN233

07:55

San Diego (SAN) 1

13:50

Midway, Chicago (MDW)

Valid until 2025-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN457

10:45

San Diego (SAN) 1

16:45

Midway, Chicago (MDW)

Effective 2025-08-09 through 2025-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN457

13:50

San Diego (SAN) 1

19:50

Midway, Chicago (MDW)

Effective 2025-08-10 through 2025-08-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN457

13:50

San Diego (SAN) 1

19:50

Midway, Chicago (MDW)

Effective 2025-09-07 through 2025-09-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN457

15:35

San Diego (SAN) 1

21:30

Midway, Chicago (MDW)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN457

16:05

San Diego (SAN) 1

22:00

Midway, Chicago (MDW)

Effective 2025-08-05 through 2025-10-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN478

16:50

San Diego (SAN) 1

22:50

Midway, Chicago (MDW)

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN478

18:45

San Diego (SAN) 1

00:45(+1)

Midway, Chicago (MDW)

Effective 2025-10-05 through 2025-10-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Southwest Airlines WN495

17:55

San Diego (SAN) 1

23:55

Midway, Chicago (MDW)

Valid until 2025-06-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN557

10:35

San Diego (SAN) 1

16:35

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

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

Southwest Airlines WN557

11:25

San Diego (SAN) 1

17:25

Midway, Chicago (MDW)

Effective 2025-06-05 through 2025-07-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN557

11:25

San Diego (SAN) 1

17:25

Midway, Chicago (MDW)

Effective 2025-07-07 through 2025-08-04

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN594

07:30

San Diego (SAN) 1

13:30

Midway, Chicago (MDW)

Effective 2025-08-09 through 2025-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN594

08:10

San Diego (SAN) 1

14:10

Midway, Chicago (MDW)

Effective 2025-08-05 through 2025-10-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN925

18:25

San Diego (SAN) 1

00:25(+1)

Midway, Chicago (MDW)

Effective 2025-10-07 through 2025-10-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN1169

06:30

San Diego (SAN) 1

12:30

Midway, Chicago (MDW)

Valid until 2025-06-02

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN1428

07:35

San Diego (SAN) 1

13:30

Midway, Chicago (MDW)

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN1428

11:15

San Diego (SAN) 1

17:15

Midway, Chicago (MDW)

Valid until 2025-06-02

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN1428

11:15

San Diego (SAN) 1

17:15

Midway, Chicago (MDW)

Valid until 2025-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN1428

13:50

San Diego (SAN) 1

19:50

Midway, Chicago (MDW)

Operates only on 2025-05-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN1428

13:50

San Diego (SAN) 1

19:50

Midway, Chicago (MDW)

Effective 2025-05-11 through 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN1428

13:50

San Diego (SAN) 1

19:50

Midway, Chicago (MDW)

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN1696

12:05

San Diego (SAN) 1

18:10

Midway, Chicago (MDW)

Operates only on 2025-11-27

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN1697

10:50

San Diego (SAN) 1

16:50

Midway, Chicago (MDW)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN1697

11:00

San Diego (SAN) 1

17:00

Midway, Chicago (MDW)

Effective 2025-08-10 through 2025-08-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN1697

11:00

San Diego (SAN) 1

17:00

Midway, Chicago (MDW)

Effective 2025-09-07 through 2025-09-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN1748

12:55

San Diego (SAN) 1

18:55

Midway, Chicago (MDW)

Effective 2025-11-25 through 2025-12-01

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN1748

12:55

San Diego (SAN) 1

18:55

Midway, Chicago (MDW)

Effective 2025-12-19 through 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN1748

13:30

San Diego (SAN) 1

19:30

Midway, Chicago (MDW)

Effective 2025-11-22 through 2025-11-29

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN1748

13:30

San Diego (SAN) 1

19:30

Midway, Chicago (MDW)

Effective 2025-12-20 through 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN1887

06:40

San Diego (SAN) 1

12:45

Midway, Chicago (MDW)

Operates only on 2025-11-27

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN1981

11:00

San Diego (SAN) 1

17:10

Midway, Chicago (MDW)

Effective 2025-10-07 through 2025-10-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2053

18:30

San Diego (SAN) 1

00:30(+1)

Midway, Chicago (MDW)

Effective 2025-08-07 through 2025-09-29

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Southwest Airlines WN2139

13:20

San Diego (SAN) 1

19:25

Midway, Chicago (MDW)

Effective 2025-10-05 through 2025-10-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2153

06:35

San Diego (SAN) 1

12:40

Midway, Chicago (MDW)

Effective 2025-11-25 through 2025-12-01

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2153

06:35

San Diego (SAN) 1

12:40

Midway, Chicago (MDW)

Effective 2025-12-19 through 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN2153

07:10

San Diego (SAN) 1

13:10

Midway, Chicago (MDW)

Effective 2025-11-22 through 2025-11-29

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2153

07:10

San Diego (SAN) 1

13:10

Midway, Chicago (MDW)

Effective 2025-12-20 through 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2189

14:15

San Diego (SAN) 1

20:10

Midway, Chicago (MDW)

Effective 2025-06-10 through 2025-07-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2206

13:40

San Diego (SAN) 1

19:40

Midway, Chicago (MDW)

Effective 2025-08-07 through 2025-09-29

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN2872

12:05

San Diego (SAN) 1

18:10

Midway, Chicago (MDW)

Effective 2025-10-02 through 2025-10-31

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN2876

19:55

San Diego (SAN) 1

01:50(+1)

Midway, Chicago (MDW)

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2876

19:55

San Diego (SAN) 1

01:50(+1)

Midway, Chicago (MDW)

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2921

11:55

San Diego (SAN) 1

18:00

Midway, Chicago (MDW)

Effective 2025-06-08 through 2025-08-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2927

07:20

San Diego (SAN) 1

13:25

Midway, Chicago (MDW)

Effective 2025-06-07 through 2025-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:05, non-stop
Boeing 737-700 (73W)

Page 1 / 3 next

A domestic route departing from the San Diego airport (SAN) and arriving at Midway, Chicago 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 3:55 and 4:10.

All SAN-MDW flights

All Southwest Airlines flights

Return (MDW-SAN) flights

Feedback - Disclaimer - Privacy