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

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FLIGHT SCHEDULE
Direct Flights:
Sat 18:45 San Diego (SAN) 1 00:40 Midway, Chicago (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-11-22 through 2025-11-29 The flight arrives 1 day after departure.
Sat 18:45 San Diego (SAN) 1 00:40 Midway, Chicago (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-12-20 through 2026-01-03 The flight arrives 1 day after departure.
Mon-Wed 19:00 San Diego (SAN) 1 00:55 Midway, Chicago (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-11-25 through 2025-12-01 The flight arrives 1 day after departure.
Mon,Tue,Fri,Sun 19:00 San Diego (SAN) 1 00:55 Midway, Chicago (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-12-19 through 2026-01-04 The flight arrives 1 day after departure.
Sun 19:15 San Diego (SAN) 1 01:10 Midway, Chicago (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2025-11-30 The flight arrives 1 day after departure.
Mon,Thu,Fri,Sun 19:35 San Diego (SAN) 1 01:30 Midway, Chicago (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-11-02 through 2025-11-16 The flight arrives 1 day after departure.
Mon,Fri,Sun 19:35 San Diego (SAN) 1 01:30 Midway, Chicago (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-11-21 through 2025-11-28 The flight arrives 1 day after departure.
Fri,Sun 19:35 San Diego (SAN) 1 01:30 Midway, Chicago (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-12-07 through 2025-12-14 The flight arrives 1 day after departure.
Thu 19:35 San Diego (SAN) 1 01:30 Midway, Chicago (MDW) Southwest Airlines WN 4602 Non-stop Boeing 737-800 (73H) 3:55 Operates only on 2025-12-18 The flight arrives 1 day after departure.
Mon 19:35 San Diego (SAN) 1 01:30 Midway, Chicago (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:
Mon,Thu,Fri 16:25 San Diego (SAN) 1 00:20 Midway, Chicago (MDW) Southwest Airlines WN 690 1-stop Boeing 737-700 (73W) 5:55 Effective 2025-08-07 through 2025-09-29 The flight arrives 1 day after departure.
Sun 14:50 San Diego (SAN) 1 22:10 Midway, Chicago (MDW) Southwest Airlines WN 700 1-stop Boeing 737 MAX 8 (7M8) 5:20 Effective 2025-10-05 through 2025-10-26
Mon,Thu,Fri 15:35 San Diego (SAN) 1 22:50 Midway, Chicago (MDW) Southwest Airlines WN 952 1-stop Boeing 737-700 (73W) 5:15 Valid until 2025-06-02
Mon,Thu,Fri 06:30 San Diego (SAN) 1 14:45 Midway, Chicago (MDW) Southwest Airlines WN 1147 1-stop Boeing 737-700 (73W) 6:15 Effective 2025-08-07 through 2025-09-29
Sun 09:05 San Diego (SAN) 1 17:10 Midway, Chicago (MDW) Southwest Airlines WN 1186 1-stop Boeing 737-700 (73W) 6:05 Operates only on 2025-08-31
Mon,Thu,Fri 16:15 San Diego (SAN) 1 23:40 Midway, Chicago (MDW) Southwest Airlines WN 1915 1-stop Boeing 737 MAX 8 (7M8) 5:25 Effective 2025-08-07 through 2025-09-29
Mon,Thu,Fri,Sun 11:10 San Diego (SAN) 1 18:30 Midway, Chicago (MDW) Southwest Airlines WN 2082 1-stop Boeing 737-700 (Scimitar Winglets) 5:20 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 11:10 San Diego (SAN) 1 18:30 Midway, Chicago (MDW) Southwest Airlines WN 2082 1-stop Boeing 737-700 (Scimitar Winglets) 5:20 Effective 2025-11-21 through 2025-11-28
Fri,Sun 11:10 San Diego (SAN) 1 18:30 Midway, Chicago (MDW) Southwest Airlines WN 2082 1-stop Boeing 737-700 (Scimitar Winglets) 5:20 Effective 2025-12-07 through 2025-12-14
Thu 11:10 San Diego (SAN) 1 18:30 Midway, Chicago (MDW) Southwest Airlines WN 2082 1-stop Boeing 737-700 (Scimitar Winglets) 5:20 Operates only on 2025-12-18
Mon 11:10 San Diego (SAN) 1 18:30 Midway, Chicago (MDW) Southwest Airlines WN 2082 1-stop Boeing 737-700 (Scimitar Winglets) 5:20 Operates only on 2026-01-05
Mon,Thu,Fri 09:20 San Diego (SAN) 1 17:25 Midway, Chicago (MDW) Southwest Airlines WN 2245 1-stop Boeing 737-700 (73W) 6:05 Effective 2025-08-07 through 2025-09-29
Sun 11:20 San Diego (SAN) 1 19:40 Midway, Chicago (MDW) Southwest Airlines WN 2515 1-stop Boeing 737-700 (73W) 6:20 Effective 2025-08-10 through 2025-08-24
Sun 11:20 San Diego (SAN) 1 19:40 Midway, Chicago (MDW) Southwest Airlines WN 2515 1-stop Boeing 737-700 (73W) 6:20 Effective 2025-09-07 through 2025-09-28
Sat 09:10 San Diego (SAN) 1 17:15 Midway, Chicago (MDW) Southwest Airlines WN 2582 1-stop Boeing 737-700 (73W) 6:05 Effective 2025-06-07 through 2025-08-02
Sun 17:15 San Diego (SAN) 1 00:55 Midway, Chicago (MDW) Southwest Airlines WN 2796 1-stop Boeing 737-800 (73H) 5:40 Effective 2025-06-08 through 2025-08-03 The flight arrives 1 day after departure.
Sun 09:30 San Diego (SAN) 1 16:30 Midway, Chicago (MDW) Southwest Airlines WN 2798 1-stop Boeing 737-700 (73W) 5:00 Operates only on 2025-05-25
Fri 14:30 San Diego (SAN) 1 22:15 Midway, Chicago (MDW) Southwest Airlines WN 2909 1-stop Boeing 737 MAX 8 (7M8) 5:45 Operates only on 2025-07-04
Sat 06:45 San Diego (SAN) 1 15:15 Midway, Chicago (MDW) Southwest Airlines WN 2989 1-stop Boeing 737 MAX 8 (7M8) 6:30 Effective 2025-10-04 through 2025-11-01
Sat 11:05 San Diego (SAN) 1 20:55 Midway, Chicago (MDW) Southwest Airlines WN 3487 1-stop Boeing 737 MAX 8 (7M8) 7:50 Effective 2025-10-04 through 2025-11-01
Sun 17:50 San Diego (SAN) 1 01:10 Midway, Chicago (MDW) Southwest Airlines WN 4994 1-stop Boeing 737 MAX 8 (7M8) 5:20 Operates only on 2025-11-30 The flight arrives 1 day after departure.
Mon,Thu,Fri 09:35 San Diego (SAN) 1 18:15 Midway, Chicago (MDW) Southwest Airlines WN 298 2-stop Boeing 737-700 (73W) 6:40 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 09:35 San Diego (SAN) 1 18:15 Midway, Chicago (MDW) Southwest Airlines WN 298 2-stop Boeing 737-700 (73W) 6:40 Effective 2025-07-07 through 2025-08-04
Tue,Wed 08:40 San Diego (SAN) 1 18:15 Midway, Chicago (MDW) Southwest Airlines WN 1537 2-stop Boeing 737-700 (73W) 7:35 Valid until 2025-06-04
Sun 09:30 San Diego (SAN) 1 19:35 Midway, Chicago (MDW) Southwest Airlines WN 1786 2-stop Boeing 737-700 (73W) 8:05 Effective 2025-08-10 through 2025-08-24
Sun 09:30 San Diego (SAN) 1 19:35 Midway, Chicago (MDW) Southwest Airlines WN 1786 2-stop Boeing 737-700 (73W) 8:05 Effective 2025-09-07 through 2025-09-28
Sun 08:40 San Diego (SAN) 1 18:50 Midway, Chicago (MDW) Southwest Airlines WN 1845 2-stop Boeing 737-700 (73W) 8:10 Valid until 2025-05-18
Sun 08:40 San Diego (SAN) 1 18:50 Midway, Chicago (MDW) Southwest Airlines WN 1845 2-stop Boeing 737-700 (73W) 8:10 Operates only on 2025-06-01
Mon-Wed 11:35 San Diego (SAN) 1 21:25 Midway, Chicago (MDW) Southwest Airlines WN 2373 2-stop Boeing 737-700 (Scimitar Winglets) 7:50 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 11:35 San Diego (SAN) 1 21:25 Midway, Chicago (MDW) Southwest Airlines WN 2373 2-stop Boeing 737-700 (Scimitar Winglets) 7:50 Effective 2025-12-19 through 2026-01-04
Mon-Wed 09:20 San Diego (SAN) 1 18:50 Midway, Chicago (MDW) Southwest Airlines WN 2826 2-stop Boeing 737-800 (73H) 7:30 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 09:20 San Diego (SAN) 1 18:50 Midway, Chicago (MDW) Southwest Airlines WN 2826 2-stop Boeing 737-800 (73H) 7:30 Effective 2025-12-19 through 2026-01-04
Sat 10:05 San Diego (SAN) 1 20:25 Midway, Chicago (MDW) Southwest Airlines WN 4170 2-stop Boeing 737-700 (73W) 8:20 Effective 2025-06-07 through 2025-08-02
Sun 09:05 San Diego (SAN) 1 21:05 Midway, Chicago (MDW) Southwest Airlines WN 2649 3-stop Boeing 737-700 (73W) 10:00 Valid until 2025-05-18
Sun 09:05 San Diego (SAN) 1 21:05 Midway, Chicago (MDW) Southwest Airlines WN 2649 3-stop Boeing 737-700 (73W) 10:00 Operates only on 2025-06-01

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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.

Return (MDW-SAN) flights

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

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FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN4602

18:45

San Diego (SAN) 1

00:40(+1)

Midway, Chicago (MDW)

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

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 WN4602

18:45

San Diego (SAN) 1

00:40(+1)

Midway, Chicago (MDW)

Effective 2025-12-20 through 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.

Southwest Airlines WN4602

19:00

San Diego (SAN) 1

00:55(+1)

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN4602

19:00

San Diego (SAN) 1

00:55(+1)

Midway, Chicago (MDW)

Effective 2025-12-19 through 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.

Southwest Airlines WN4602

19:15

San Diego (SAN) 1

01:10(+1)

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN4602

19:35

San Diego (SAN) 1

01:30(+1)

Midway, Chicago (MDW)

Effective 2025-11-02 through 2025-11-16

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 WN4602

19:35

San Diego (SAN) 1

01:30(+1)

Midway, Chicago (MDW)

Effective 2025-11-21 through 2025-11-28

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 WN4602

19:35

San Diego (SAN) 1

01:30(+1)

Midway, Chicago (MDW)

Effective 2025-12-07 through 2025-12-14

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 WN4602

19:35

San Diego (SAN) 1

01:30(+1)

Midway, Chicago (MDW)

Operates only on 2025-12-18

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 WN4602

19:35

San Diego (SAN) 1

01:30(+1)

Midway, Chicago (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 WN690

16:25

San Diego (SAN) 1

00:20(+1)

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 5:55, 1-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Southwest Airlines WN700

14:50

San Diego (SAN) 1

22:10

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:20, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN952

15:35

San Diego (SAN) 1

22:50

Midway, Chicago (MDW)

Valid until 2025-06-02

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 5:15, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN1147

06:30

San Diego (SAN) 1

14:45

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:15, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN1186

09:05

San Diego (SAN) 1

17:10

Midway, Chicago (MDW)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:05, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN1915

16:15

San Diego (SAN) 1

23:40

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 5:25, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2082

11:10

San Diego (SAN) 1

18:30

Midway, Chicago (MDW)

Effective 2025-11-02 through 2025-11-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Southwest Airlines WN2082

11:10

San Diego (SAN) 1

18:30

Midway, Chicago (MDW)

Effective 2025-11-21 through 2025-11-28

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN2082

11:10

San Diego (SAN) 1

18:30

Midway, Chicago (MDW)

Effective 2025-12-07 through 2025-12-14

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN2082

11:10

San Diego (SAN) 1

18:30

Midway, Chicago (MDW)

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2082

11:10

San Diego (SAN) 1

18:30

Midway, Chicago (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2245

09:20

San Diego (SAN) 1

17:25

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:05, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN2515

11:20

San Diego (SAN) 1

19:40

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:20, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN2515

11:20

San Diego (SAN) 1

19:40

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:20, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN2582

09:10

San Diego (SAN) 1

17:15

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:05, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN2796

17:15

San Diego (SAN) 1

00:55(+1)

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:40, 1-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Southwest Airlines WN2798

09:30

San Diego (SAN) 1

16:30

Midway, Chicago (MDW)

Operates only on 2025-05-25

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:00, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN2909

14:30

San Diego (SAN) 1

22:15

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

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

Southwest Airlines WN2989

06:45

San Diego (SAN) 1

15:15

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN3487

11:05

San Diego (SAN) 1

20:55

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN4994

17:50

San Diego (SAN) 1

01:10(+1)

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:20, 1-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN298

09:35

San Diego (SAN) 1

18:15

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:40, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN298

09:35

San Diego (SAN) 1

18:15

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:40, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN1537

08:40

San Diego (SAN) 1

18:15

Midway, Chicago (MDW)

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 7:35, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN1786

09:30

San Diego (SAN) 1

19:35

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 8:05, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN1786

09:30

San Diego (SAN) 1

19:35

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 8:05, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN1845

08:40

San Diego (SAN) 1

18:50

Midway, Chicago (MDW)

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 8:10, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN1845

08:40

San Diego (SAN) 1

18:50

Midway, Chicago (MDW)

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 8:10, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN2373

11:35

San Diego (SAN) 1

21:25

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 7:50, 2-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2373

11:35

San Diego (SAN) 1

21:25

Midway, Chicago (MDW)

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

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 7:50, 2-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2826

09:20

San Diego (SAN) 1

18:50

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 7:30, 2-stop
Boeing 737-800 (73H)

Southwest Airlines WN2826

09:20

San Diego (SAN) 1

18:50

Midway, Chicago (MDW)

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

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 7:30, 2-stop
Boeing 737-800 (73H)

Southwest Airlines WN4170

10:05

San Diego (SAN) 1

20:25

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 8:20, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN2649

09:05

San Diego (SAN) 1

21:05

Midway, Chicago (MDW)

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 10:00, 3-stop
Boeing 737-700 (73W)

Southwest Airlines WN2649

09:05

San Diego (SAN) 1

21:05

Midway, Chicago (MDW)

Operates only on 2025-06-01

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Sun

Duration: 10:00, 3-stop
Boeing 737-700 (73W)

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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.

Return (MDW-SAN) flights

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