All airlines flying from Chicago Midway (MDW) to Oakland (OAK).

FLIGHT SCHEDULE
Non-Direct Flights:
Tue,Wed 15:55 Chicago Midway (MDW) 20:20 Oakland (OAK) 2 Southwest Airlines WN 946 1-stop Boeing 737 MAX 8 (7M8) 6:25 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 10:15 Chicago Midway (MDW) 14:20 Oakland (OAK) 2 Southwest Airlines WN 1049 1-stop Boeing 737-700 (Scimitar Winglets) 6:05 Effective 2026-03-05 through 2026-04-06
Sat 16:20 Chicago Midway (MDW) 21:35 Oakland (OAK) 2 Southwest Airlines WN 1085 1-stop Boeing 737-800 (73H) 7:15 Effective 2026-02-14 through 2026-02-28
Mon,Tue,Fri,Sun 15:55 Chicago Midway (MDW) 20:30 Oakland (OAK) 2 Southwest Airlines WN 2256 1-stop Boeing 737 MAX 8 (7M8) 6:35 Valid until 2026-01-04
Mon,Thu,Fri 20:15 Chicago Midway (MDW) 00:15 Oakland (OAK) 2 Southwest Airlines WN 2289 1-stop Boeing 737 MAX 8 (7M8) 6:00 Effective 2026-06-04 through 2026-08-03 The flight arrives 1 day after departure.
Sat 14:55 Chicago Midway (MDW) 19:20 Oakland (OAK) 2 Southwest Airlines WN 2418 1-stop Boeing 737 MAX 8 (7M8) 6:25 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 15:40 Chicago Midway (MDW) 19:55 Oakland (OAK) 2 Southwest Airlines WN 2677 1-stop Boeing 737 MAX 8 (7M8) 6:15 Effective 2026-04-09 through 2026-06-01
Mon,Thu,Fri 13:30 Chicago Midway (MDW) 18:10 Oakland (OAK) 2 Southwest Airlines WN 2740 1-stop Boeing 737-800 (73H) 6:40 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 13:30 Chicago Midway (MDW) 18:10 Oakland (OAK) 2 Southwest Airlines WN 2740 1-stop Boeing 737-800 (73H) 6:40 Effective 2026-02-20 through 2026-03-01
Mon,Thu,Fri 17:15 Chicago Midway (MDW) 22:35 Oakland (OAK) 2 Southwest Airlines WN 2890 1-stop Boeing 737 MAX 8 (7M8) 7:20 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 10:00 Chicago Midway (MDW) 13:50 Oakland (OAK) 2 Southwest Airlines WN 2951 1-stop Boeing 737-700 (Scimitar Winglets) 5:50 Effective 2026-06-04 through 2026-08-03
Tue,Wed 05:40 Chicago Midway (MDW) 09:55 Oakland (OAK) 2 Southwest Airlines WN 3014 1-stop Boeing 737 MAX 8 (7M8) 6:15 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 17:40 Chicago Midway (MDW) 22:20 Oakland (OAK) 2 Southwest Airlines WN 3034 1-stop Boeing 737 MAX 8 (7M8) 6:40 Effective 2026-03-05 through 2026-04-06
Sat 06:55 Chicago Midway (MDW) 11:10 Oakland (OAK) 2 Southwest Airlines WN 3285 1-stop Boeing 737-800 (73H) 6:15 Effective 2026-04-11 through 2026-05-30
Sun 16:50 Chicago Midway (MDW) 21:15 Oakland (OAK) 2 Southwest Airlines WN 3572 1-stop Boeing 737 MAX 8 (7M8) 6:25 Effective 2026-03-08 through 2026-04-05
Tue,Wed 10:10 Chicago Midway (MDW) 14:55 Oakland (OAK) 2 Southwest Airlines WN 3579 1-stop Boeing 737 MAX 8 (7M8) 6:45 Effective 2026-04-07 through 2026-06-03
Tue,Wed 13:55 Chicago Midway (MDW) 18:35 Oakland (OAK) 2 Southwest Airlines WN 4236 1-stop Boeing 737-700 (Scimitar Winglets) 6:40 Effective 2026-03-10 through 2026-04-01
Sun 07:45 Chicago Midway (MDW) 13:20 Oakland (OAK) 2 Southwest Airlines WN 1050 2-stop Boeing 737-800 (73H) 7:35 Effective 2026-04-12 through 2026-05-17
Sun 07:45 Chicago Midway (MDW) 13:20 Oakland (OAK) 2 Southwest Airlines WN 1050 2-stop Boeing 737-800 (73H) 7:35 Operates only on 2026-05-31
Mon,Thu,Fri 16:55 Chicago Midway (MDW) 22:45 Oakland (OAK) 2 Southwest Airlines WN 1052 2-stop Boeing 737-700 (Scimitar Winglets) 7:50 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 16:55 Chicago Midway (MDW) 22:45 Oakland (OAK) 2 Southwest Airlines WN 1052 2-stop Boeing 737-700 (Scimitar Winglets) 7:50 Effective 2026-02-20 through 2026-03-01
Tue,Wed 15:25 Chicago Midway (MDW) 21:35 Oakland (OAK) 2 Southwest Airlines WN 1188 2-stop Boeing 737-800 (73H) 8:10 Effective 2026-03-10 through 2026-04-01
Sun 10:45 Chicago Midway (MDW) 20:30 Oakland (OAK) 2 Southwest Airlines WN 2192 3-stop Boeing 737-700 (Scimitar Winglets) 11:45 Effective 2026-03-08 through 2026-04-05
Sun 11:05 Chicago Midway (MDW) 18:25 Oakland (OAK) 2 Southwest Airlines WN 2914 3-stop Boeing 737-700 (Scimitar Winglets) 9:20 Effective 2026-03-08 through 2026-04-05

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A domestic route departing from the Chicago Midway airport (MDW) and arriving at Oakland airport (OAK).
The flight distance is 1839 miles, or 2959 km.
The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-8 . 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 4:25 and 4:55.

Return (OAK-MDW) flights

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All airlines flying from Chicago Midway (MDW) to Oakland (OAK).

FLIGHT SCHEDULE

Non-Direct Flights:

Southwest Airlines WN946

15:55

Chicago Midway (MDW)

20:20

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1049

10:15

Chicago Midway (MDW)

14:20

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1085

16:20

Chicago Midway (MDW)

21:35

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 7:15, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN2256

15:55

Chicago Midway (MDW)

20:30

Oakland (OAK) 2

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 6:35, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2289

20:15

Chicago Midway (MDW)

00:15(+1)

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:00, 1-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Non-Direct Flights:

Southwest Airlines WN2418

14:55

Chicago Midway (MDW)

19:20

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2677

15:40

Chicago Midway (MDW)

19:55

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2740

13:30

Chicago Midway (MDW)

18:10

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:40, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN2740

13:30

Chicago Midway (MDW)

18:10

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 6:40, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN2890

17:15

Chicago Midway (MDW)

22:35

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN2951

10:00

Chicago Midway (MDW)

13:50

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 5:50, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3014

05:40

Chicago Midway (MDW)

09:55

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3034

17:40

Chicago Midway (MDW)

22:20

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:40, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3285

06:55

Chicago Midway (MDW)

11:10

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN3572

16:50

Chicago Midway (MDW)

21:15

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3579

10:10

Chicago Midway (MDW)

14:55

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:45, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4236

13:55

Chicago Midway (MDW)

18:35

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1050

07:45

Chicago Midway (MDW)

13:20

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:35, 2-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN1050

07:45

Chicago Midway (MDW)

13:20

Oakland (OAK) 2

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:35, 2-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN1052

16:55

Chicago Midway (MDW)

22:45

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN1052

16:55

Chicago Midway (MDW)

22:45

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN1188

15:25

Chicago Midway (MDW)

21:35

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 8:10, 2-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN2192

10:45

Chicago Midway (MDW)

20:30

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 11:45, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2914

11:05

Chicago Midway (MDW)

18:25

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 9:20, 3-stop
Boeing 737-700 (Scimitar Winglets)

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A domestic route departing from the Chicago Midway airport (MDW) and arriving at Oakland airport (OAK).
The flight distance is 1839 miles, or 2959 km.
The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-8 . 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 4:25 and 4:55.

Return (OAK-MDW) flights

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