All airlines flying from San Francisco (SFO) to Chicago Midway (MDW).

FLIGHT SCHEDULE
Direct Flights:
Wed 10:30 San Francisco (SFO) 2 16:40 Chicago Midway (MDW) Southwest Airlines WN 265 Non-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-08-05 through 2026-09-30
Mon,Thu,Fri 05:45 San Francisco (SFO) 2 11:50 Chicago Midway (MDW) Southwest Airlines WN 717 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-08-06 through 2026-09-28
Mon,Tue,Fri,Sun 06:45 San Francisco (SFO) 2 12:45 Chicago Midway (MDW) Southwest Airlines WN 1475 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Valid until 2026-01-04
Sat 05:25 San Francisco (SFO) 2 11:30 Chicago Midway (MDW) Southwest Airlines WN 1779 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 05:40 San Francisco (SFO) 2 11:45 Chicago Midway (MDW) Southwest Airlines WN 1779 Non-stop Boeing 737-800 (73H) 4:05 Effective 2026-06-04 through 2026-08-03
Sun 08:10 San Francisco (SFO) 2 14:10 Chicago Midway (MDW) Southwest Airlines WN 1779 Non-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-06-07 through 2026-08-02
Mon 06:10 San Francisco (SFO) 2 12:15 Chicago Midway (MDW) Southwest Airlines WN 1939 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2026-01-05
Thu,Fri 23:25 San Francisco (SFO) 2 05:30 Chicago Midway (MDW) Southwest Airlines WN 1945 Non-stop Boeing 737-800 (73H) 4:05 Effective 2026-03-05 through 2026-03-06 The flight arrives 1 day after departure.
Daily 23:25 San Francisco (SFO) 2 05:30 Chicago Midway (MDW) Southwest Airlines WN 1945 Non-stop Boeing 737-800 (73H) 4:05 Effective 2026-03-08 through 2026-04-06 The flight arrives 1 day after departure.
Fri 05:50 San Francisco (SFO) 2 11:50 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Operates only on 2026-02-20
Mon,Thu,Fri 05:55 San Francisco (SFO) 2 11:55 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 05:55 San Francisco (SFO) 2 11:55 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-02-22 through 2026-03-01
Thu,Fri,Sun 06:25 San Francisco (SFO) 2 12:25 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-01-11 through 2026-01-16
Mon,Sun 06:25 San Francisco (SFO) 2 12:25 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 06:25 San Francisco (SFO) 2 12:25 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-02-01 through 2026-02-06
Mon,Sun 06:25 San Francisco (SFO) 2 12:25 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 06:25 San Francisco (SFO) 2 12:25 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-02-17 through 2026-02-23
Mon 06:25 San Francisco (SFO) 2 12:25 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737-800 (73H) 4:00 Operates only on 2026-03-02
Sat 06:55 San Francisco (SFO) 2 12:55 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-02-14 through 2026-02-28
Sat 10:25 San Francisco (SFO) 2 16:20 Chicago Midway (MDW) Southwest Airlines WN 2080 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-01-10 through 2026-02-07
Sat 05:45 San Francisco (SFO) 2 11:45 Chicago Midway (MDW) Southwest Airlines WN 2120 Non-stop Boeing 737-800 (73H) 4:00 Valid until 2026-01-03
Sat 23:25 San Francisco (SFO) 2 06:30 Chicago Midway (MDW) Southwest Airlines WN 2136 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2026-03-07 The flight arrives 1 day after departure.
Mon,Thu,Fri 05:20 San Francisco (SFO) 2 11:25 Chicago Midway (MDW) Southwest Airlines WN 2318 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-04-09 through 2026-06-01
Sun 05:25 San Francisco (SFO) 2 11:30 Chicago Midway (MDW) Southwest Airlines WN 2318 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-04-12 through 2026-05-17
Sun 05:25 San Francisco (SFO) 2 11:30 Chicago Midway (MDW) Southwest Airlines WN 2318 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2026-05-31
Tue,Wed 05:30 San Francisco (SFO) 2 11:35 Chicago Midway (MDW) Southwest Airlines WN 2318 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-04-07 through 2026-05-20
Tue,Wed,Sun 05:30 San Francisco (SFO) 2 11:35 Chicago Midway (MDW) Southwest Airlines WN 2318 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-05-24 through 2026-05-27
Tue,Wed 05:30 San Francisco (SFO) 2 11:35 Chicago Midway (MDW) Southwest Airlines WN 2318 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-06-02 through 2026-06-03
Sat 08:20 San Francisco (SFO) 2 14:25 Chicago Midway (MDW) Southwest Airlines WN 2318 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-04-11 through 2026-05-30
Wed,Thu 06:10 San Francisco (SFO) 2 12:15 Chicago Midway (MDW) Southwest Airlines WN 3443 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Valid until 2026-01-01
Tue 10:30 San Francisco (SFO) 2 16:40 Chicago Midway (MDW) Southwest Airlines WN 3532 Non-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-08-04 through 2026-09-29
Daily 23:40 San Francisco (SFO) 2 05:50 Chicago Midway (MDW) Southwest Airlines WN 3556 Non-stop Boeing 737-800 (73H) 4:10 Effective 2026-08-04 through 2026-09-30 The flight arrives 1 day after departure.
Daily 23:40 San Francisco (SFO) 2 05:50 Chicago Midway (MDW) Southwest Airlines WN 3649 Non-stop Boeing 737-800 (73H) 4:10 Effective 2026-06-04 through 2026-08-03 The flight arrives 1 day after departure.
Tue,Wed 05:10 San Francisco (SFO) 2 11:15 Chicago Midway (MDW) Southwest Airlines WN 3901 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri,Sun 05:10 San Francisco (SFO) 2 11:10 Chicago Midway (MDW) Southwest Airlines WN 3938 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-03-05 through 2026-04-06
Sat 05:15 San Francisco (SFO) 2 11:10 Chicago Midway (MDW) Southwest Airlines WN 3938 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-03-07 through 2026-04-04
Tue,Wed 05:40 San Francisco (SFO) 2 11:40 Chicago Midway (MDW) Southwest Airlines WN 3938 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-03-10 through 2026-04-01
Daily 23:25 San Francisco (SFO) 2 05:40 Chicago Midway (MDW) Southwest Airlines WN 4216 Non-stop Boeing 737-800 (73H) 4:15 Effective 2026-04-07 through 2026-06-03 The flight arrives 1 day after departure.
Sat 08:00 San Francisco (SFO) 2 14:00 Chicago Midway (MDW) Southwest Airlines WN 4530 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-08-08 through 2026-09-26
Sun 08:40 San Francisco (SFO) 2 14:55 Chicago Midway (MDW) Southwest Airlines WN 4898 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-08-09 through 2026-09-27
Non-Direct Flights:
Sat 10:05 San Francisco (SFO) 2 17:30 Chicago Midway (MDW) Southwest Airlines WN 1405 1-stop Boeing 737-700 (Scimitar Winglets) 5:25 Operates only on 2026-01-03
Sat 10:15 San Francisco (SFO) 2 17:40 Chicago Midway (MDW) Southwest Airlines WN 1955 1-stop Boeing 737-700 (Scimitar Winglets) 5:25 Effective 2026-04-11 through 2026-05-30
Tue,Wed 10:40 San Francisco (SFO) 2 18:30 Chicago Midway (MDW) Southwest Airlines WN 3026 1-stop Boeing 737 MAX 8 (7M8) 5:50 Effective 2026-03-10 through 2026-04-01
Sun 09:50 San Francisco (SFO) 2 17:40 Chicago Midway (MDW) Southwest Airlines WN 4249 1-stop Boeing 737 MAX 8 (7M8) 5:50 Effective 2026-06-07 through 2026-08-02
Thu,Fri,Sun 07:35 San Francisco (SFO) 2 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 2-stop Boeing 737-700 (Scimitar Winglets) 7:25 Effective 2026-01-11 through 2026-01-16
Sun 07:35 San Francisco (SFO) 2 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 2-stop Boeing 737-700 (Scimitar Winglets) 7:25 Effective 2026-01-25 through 2026-02-01
Mon,Thu,Fri 07:35 San Francisco (SFO) 2 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 2-stop Boeing 737-700 (Scimitar Winglets) 7:25 Effective 2026-02-05 through 2026-02-09
Tue,Thu,Sun 07:35 San Francisco (SFO) 2 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 2-stop Boeing 737-700 (Scimitar Winglets) 7:25 Effective 2026-02-15 through 2026-02-19
Mon 07:35 San Francisco (SFO) 2 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 2-stop Boeing 737-700 (Scimitar Winglets) 7:25 Effective 2026-02-23 through 2026-03-02

A domestic route departing from the San Francisco airport (SFO) and arriving at Chicago Midway airport (MDW).
The flight distance is 1849 miles, or 2975 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 4:15.

Return (MDW-SFO) flights

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All airlines flying from San Francisco (SFO) to Chicago Midway (MDW).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN265

10:30

San Francisco (SFO) 2

16:40

Chicago Midway (MDW)

Effective 2026-08-05 through 2026-09-30

Mon
-

Tue
-

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN717

05:45

San Francisco (SFO) 2

11:50

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1475

06:45

San Francisco (SFO) 2

12:45

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 WN1779

05:25

San Francisco (SFO) 2

11:30

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1779

05:40

San Francisco (SFO) 2

11:45

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1779

08:10

San Francisco (SFO) 2

14:10

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)

Direct Flights:

Southwest Airlines WN1939

06:10

San Francisco (SFO) 2

12:15

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 WN1945

23:25

San Francisco (SFO) 2

05:30(+1)

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:05, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN1945

23:25

San Francisco (SFO) 2

05:30(+1)

Chicago Midway (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat

Sun

Duration: 4:05, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN2080

05:50

San Francisco (SFO) 2

11:50

Chicago Midway (MDW)

Operates only on 2026-02-20

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2080

05:55

San Francisco (SFO) 2

11:55

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2080

05:55

San Francisco (SFO) 2

11:55

Chicago Midway (MDW)

Effective 2026-02-22 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2080

06:25

San Francisco (SFO) 2

12:25

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2080

06:25

San Francisco (SFO) 2

12:25

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2080

06:25

San Francisco (SFO) 2

12:25

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2080

06:25

San Francisco (SFO) 2

12:25

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2080

06:25

San Francisco (SFO) 2

12:25

Chicago Midway (MDW)

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

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2080

06:25

San Francisco (SFO) 2

12:25

Chicago Midway (MDW)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2080

06:55

San Francisco (SFO) 2

12:55

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN2080

10:25

San Francisco (SFO) 2

16:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN2120

05:45

San Francisco (SFO) 2

11:45

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 WN2136

23:25

San Francisco (SFO) 2

06:30(+1)

Chicago Midway (MDW)

Operates only on 2026-03-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:05, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN2318

05:20

San Francisco (SFO) 2

11:25

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2318

05:25

San Francisco (SFO) 2

11:30

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2318

05:25

San Francisco (SFO) 2

11:30

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2318

05:30

San Francisco (SFO) 2

11:35

Chicago Midway (MDW)

Effective 2026-04-07 through 2026-05-20

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2318

05:30

San Francisco (SFO) 2

11:35

Chicago Midway (MDW)

Effective 2026-05-24 through 2026-05-27

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2318

05:30

San Francisco (SFO) 2

11:35

Chicago Midway (MDW)

Effective 2026-06-02 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2318

08:20

San Francisco (SFO) 2

14:25

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN3443

06:10

San Francisco (SFO) 2

12:15

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 WN3532

10:30

San Francisco (SFO) 2

16:40

Chicago Midway (MDW)

Effective 2026-08-04 through 2026-09-29

Mon
-

Tue

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN3556

23:40

San Francisco (SFO) 2

05:50(+1)

Chicago Midway (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat

Sun

Duration: 4:10, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3649

23:40

San Francisco (SFO) 2

05:50(+1)

Chicago Midway (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat

Sun

Duration: 4:10, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3901

05:10

San Francisco (SFO) 2

11:15

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3938

05:10

San Francisco (SFO) 2

11:10

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 WN3938

05:15

San Francisco (SFO) 2

11:10

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN3938

05:40

San Francisco (SFO) 2

11:40

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4216

23:25

San Francisco (SFO) 2

05:40(+1)

Chicago Midway (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat

Sun

Duration: 4:15, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN4530

08:00

San Francisco (SFO) 2

14:00

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 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4898

08:40

San Francisco (SFO) 2

14:55

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:15, non-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1405

10:05

San Francisco (SFO) 2

17:30

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1955

10:15

San Francisco (SFO) 2

17:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3026

10:40

San Francisco (SFO) 2

18:30

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN4249

09:50

San Francisco (SFO) 2

17:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN256

07:35

San Francisco (SFO) 2

17:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 7:25, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN256

07:35

San Francisco (SFO) 2

17:00

Chicago Midway (MDW)

Effective 2026-01-25 through 2026-02-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:25, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN256

07:35

San Francisco (SFO) 2

17:00

Chicago Midway (MDW)

Effective 2026-02-05 through 2026-02-09

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 7:25, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN256

07:35

San Francisco (SFO) 2

17:00

Chicago Midway (MDW)

Effective 2026-02-15 through 2026-02-19

Mon
-

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun

Duration: 7:25, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN256

07:35

San Francisco (SFO) 2

17:00

Chicago Midway (MDW)

Effective 2026-02-23 through 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 7:25, 2-stop
Boeing 737-700 (Scimitar Winglets)

A domestic route departing from the San Francisco airport (SFO) and arriving at Chicago Midway airport (MDW).
The flight distance is 1849 miles, or 2975 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 4:15.

Return (MDW-SFO) flights

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