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

FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 11:05 San Diego (SAN) 1 17:00 Chicago Midway (MDW) Southwest Airlines WN 103 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-08-06 through 2026-09-28
Mon,Thu,Fri 22:40 San Diego (SAN) 1 04:40 Chicago Midway (MDW) Southwest Airlines WN 257 Non-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-06-04 through 2026-08-03 The flight arrives 1 day after departure.
Sat 22:40 San Diego (SAN) 1 04:40 Chicago Midway (MDW) Southwest Airlines WN 354 Non-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-06-06 through 2026-08-01 The flight arrives 1 day after departure.
Sun 22:40 San Diego (SAN) 1 04:40 Chicago Midway (MDW) Southwest Airlines WN 560 Non-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-06-07 through 2026-08-02 The flight arrives 1 day after departure.
Mon,Thu,Fri 06:45 San Diego (SAN) 1 12:45 Chicago Midway (MDW) Southwest Airlines WN 770 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-08-06 through 2026-09-28
Sun 15:05 San Diego (SAN) 1 21:00 Chicago Midway (MDW) Southwest Airlines WN 770 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-08-09 through 2026-09-27
Tue,Wed 22:40 San Diego (SAN) 1 04:40 Chicago Midway (MDW) Southwest Airlines WN 840 Non-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-06-09 through 2026-07-29 The flight arrives 1 day after departure.
Thu,Fri 22:40 San Diego (SAN) 1 04:35 Chicago Midway (MDW) Southwest Airlines WN 990 Non-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-03-05 through 2026-03-06 The flight arrives 1 day after departure.
Daily 22:40 San Diego (SAN) 1 04:35 Chicago Midway (MDW) Southwest Airlines WN 990 Non-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-03-08 through 2026-04-06 The flight arrives 1 day after departure.
Mon-Fri 06:25 San Diego (SAN) 1 12:25 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 06:25 San Diego (SAN) 1 12:25 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-01-18 through 2026-01-23
Mon-Fri 06:25 San Diego (SAN) 1 12:25 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 06:25 San Diego (SAN) 1 12:25 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-02-08 through 2026-02-11
Tue,Wed 06:25 San Diego (SAN) 1 12:25 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-02-18 through 2026-03-04
Thu,Fri,Sun 06:45 San Diego (SAN) 1 12:40 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-01-11 through 2026-01-16
Mon,Sun 06:45 San Diego (SAN) 1 12:40 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 06:45 San Diego (SAN) 1 12:40 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-02-01 through 2026-02-06
Mon,Sun 06:45 San Diego (SAN) 1 12:40 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 06:45 San Diego (SAN) 1 12:40 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-02-17 through 2026-02-23
Mon 06:45 San Diego (SAN) 1 12:40 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2026-03-02
Sat 07:25 San Diego (SAN) 1 13:20 Chicago Midway (MDW) Southwest Airlines WN 1209 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-01-10 through 2026-02-07
Sat 10:45 San Diego (SAN) 1 16:45 Chicago Midway (MDW) Southwest Airlines WN 1677 Non-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-06-06 through 2026-08-01
Mon,Tue,Fri,Sun 12:55 San Diego (SAN) 1 18:55 Chicago Midway (MDW) Southwest Airlines WN 1748 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Valid until 2026-01-04
Sat 13:25 San Diego (SAN) 1 19:25 Chicago Midway (MDW) Southwest Airlines WN 1748 Non-stop Boeing 737-800 (73H) 4:00 Valid until 2026-01-03
Mon-Fri 10:05 San Diego (SAN) 1 16:05 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 10:05 San Diego (SAN) 1 16:05 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-01-18 through 2026-01-23
Mon-Fri 10:05 San Diego (SAN) 1 16:05 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 10:05 San Diego (SAN) 1 16:05 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-02-08 through 2026-02-11
Tue,Wed 10:05 San Diego (SAN) 1 16:05 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-02-18 through 2026-03-04
Thu,Fri,Sun 18:30 San Diego (SAN) 1 00:25 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-01-11 through 2026-01-16 The flight arrives 1 day after departure.
Mon,Sun 18:30 San Diego (SAN) 1 00:25 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-01-19 through 2026-01-25 The flight arrives 1 day after departure.
Thu,Fri,Sun 18:30 San Diego (SAN) 1 00:25 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-01 through 2026-02-06 The flight arrives 1 day after departure.
Mon,Sun 18:30 San Diego (SAN) 1 00:25 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-09 through 2026-02-15 The flight arrives 1 day after departure.
Mon,Tue,Thu 18:30 San Diego (SAN) 1 00:25 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-17 through 2026-02-23 The flight arrives 1 day after departure.
Mon 18:30 San Diego (SAN) 1 00:25 Chicago Midway (MDW) Southwest Airlines WN 1934 Non-stop Boeing 737-800 (73H) 3:55 Operates only on 2026-03-02 The flight arrives 1 day after departure.
Mon,Tue,Fri,Sun 06:35 San Diego (SAN) 1 12:40 Chicago Midway (MDW) Southwest Airlines WN 2153 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Valid until 2026-01-04
Sat 07:10 San Diego (SAN) 1 13:10 Chicago Midway (MDW) Southwest Airlines WN 2153 Non-stop Boeing 737-800 (73H) 4:00 Valid until 2026-01-03
Sat 22:40 San Diego (SAN) 1 05:35 Chicago Midway (MDW) Southwest Airlines WN 2202 Non-stop Boeing 737-700 (Scimitar Winglets) 3:55 Operates only on 2026-03-07 The flight arrives 1 day after departure.
Tue,Wed,Sun 06:30 San Diego (SAN) 1 12:35 Chicago Midway (MDW) Southwest Airlines WN 2709 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 06:35 San Diego (SAN) 1 12:35 Chicago Midway (MDW) Southwest Airlines WN 2709 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-03-05 through 2026-04-06
Sat 06:45 San Diego (SAN) 1 12:45 Chicago Midway (MDW) Southwest Airlines WN 2709 Non-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 15:45 San Diego (SAN) 1 21:35 Chicago Midway (MDW) Southwest Airlines WN 2712 Non-stop Boeing 737-700 (Scimitar Winglets) 3:50 Effective 2026-04-09 through 2026-06-01
Sun 11:05 San Diego (SAN) 1 17:00 Chicago Midway (MDW) Southwest Airlines WN 3068 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-03-08 through 2026-04-05
Sat 06:20 San Diego (SAN) 1 12:20 Chicago Midway (MDW) Southwest Airlines WN 3292 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-04-11 through 2026-05-30
Sun 06:30 San Diego (SAN) 1 12:30 Chicago Midway (MDW) Southwest Airlines WN 3292 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-04-12 through 2026-05-17
Sun 06:30 San Diego (SAN) 1 12:30 Chicago Midway (MDW) Southwest Airlines WN 3292 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Operates only on 2026-05-31
Mon,Thu,Fri 06:40 San Diego (SAN) 1 12:35 Chicago Midway (MDW) Southwest Airlines WN 3292 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-04-09 through 2026-06-01
Tue,Wed 10:40 San Diego (SAN) 1 16:35 Chicago Midway (MDW) Southwest Airlines WN 3292 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 06:50 San Diego (SAN) 1 12:45 Chicago Midway (MDW) Southwest Airlines WN 3402 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 06:50 San Diego (SAN) 1 12:45 Chicago Midway (MDW) Southwest Airlines WN 3402 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-20 through 2026-03-01

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 WN103

11:05

San Diego (SAN) 1

17:00

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN257

22:40

San Diego (SAN) 1

04:40(+1)

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN354

22:40

San Diego (SAN) 1

04:40(+1)

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN560

22:40

San Diego (SAN) 1

04:40(+1)

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN770

06:45

San Diego (SAN) 1

12:45

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN770

15:05

San Diego (SAN) 1

21:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN840

22:40

San Diego (SAN) 1

04:40(+1)

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN990

22:40

San Diego (SAN) 1

04:35(+1)

Chicago Midway (MDW)

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

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 WN990

22:40

San Diego (SAN) 1

04:35(+1)

Chicago Midway (MDW)

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

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 WN1209

06:25

San Diego (SAN) 1

12:25

Chicago Midway (MDW)

Effective 2026-01-06 through 2026-01-14

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1209

06:25

San Diego (SAN) 1

12:25

Chicago Midway (MDW)

Effective 2026-01-18 through 2026-01-23

Mon
-

Tue

Wed

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1209

06:25

San Diego (SAN) 1

12:25

Chicago Midway (MDW)

Effective 2026-01-26 through 2026-02-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1209

06:25

San Diego (SAN) 1

12:25

Chicago Midway (MDW)

Effective 2026-02-08 through 2026-02-11

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1209

06:25

San Diego (SAN) 1

12:25

Chicago Midway (MDW)

Effective 2026-02-18 through 2026-03-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1209

06:45

San Diego (SAN) 1

12:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1209

06:45

San Diego (SAN) 1

12:40

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1209

06:45

San Diego (SAN) 1

12:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1209

06:45

San Diego (SAN) 1

12:40

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1209

06:45

San Diego (SAN) 1

12:40

Chicago Midway (MDW)

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

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1209

06:45

San Diego (SAN) 1

12:40

Chicago Midway (MDW)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1209

07:25

San Diego (SAN) 1

13:20

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1677

10:45

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

Direct Flights:

Southwest Airlines WN1748

12:55

San Diego (SAN) 1

18:55

Chicago Midway (MDW)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1748

13:25

San Diego (SAN) 1

19:25

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1934

10:05

San Diego (SAN) 1

16:05

Chicago Midway (MDW)

Effective 2026-01-06 through 2026-01-14

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1934

10:05

San Diego (SAN) 1

16:05

Chicago Midway (MDW)

Effective 2026-01-18 through 2026-01-23

Mon
-

Tue

Wed

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1934

10:05

San Diego (SAN) 1

16:05

Chicago Midway (MDW)

Effective 2026-01-26 through 2026-02-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1934

10:05

San Diego (SAN) 1

16:05

Chicago Midway (MDW)

Effective 2026-02-08 through 2026-02-11

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1934

10:05

San Diego (SAN) 1

16:05

Chicago Midway (MDW)

Effective 2026-02-18 through 2026-03-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1934

18:30

San Diego (SAN) 1

00:25(+1)

Chicago Midway (MDW)

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

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 WN1934

18:30

San Diego (SAN) 1

00:25(+1)

Chicago Midway (MDW)

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

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 WN1934

18:30

San Diego (SAN) 1

00:25(+1)

Chicago Midway (MDW)

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

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 WN1934

18:30

San Diego (SAN) 1

00:25(+1)

Chicago Midway (MDW)

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

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 WN1934

18:30

San Diego (SAN) 1

00:25(+1)

Chicago Midway (MDW)

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

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 WN1934

18:30

San Diego (SAN) 1

00:25(+1)

Chicago Midway (MDW)

Operates only on 2026-03-02

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 WN2153

06:35

San Diego (SAN) 1

12:40

Chicago Midway (MDW)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2153

07:10

San Diego (SAN) 1

13:10

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN2202

22:40

San Diego (SAN) 1

05:35(+1)

Chicago Midway (MDW)

Operates only on 2026-03-07

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 WN2709

06:30

San Diego (SAN) 1

12:35

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2709

06:35

San Diego (SAN) 1

12:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2709

06:45

San Diego (SAN) 1

12:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN2712

15:45

San Diego (SAN) 1

21:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3068

11:05

San Diego (SAN) 1

17:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN3292

06:20

San Diego (SAN) 1

12:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN3292

06:30

San Diego (SAN) 1

12:30

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3292

06:30

San Diego (SAN) 1

12:30

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN3292

06:40

San Diego (SAN) 1

12:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN3292

10:40

San Diego (SAN) 1

16:35

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3402

06:50

San Diego (SAN) 1

12:45

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN3402

06:50

San Diego (SAN) 1

12:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

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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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