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

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FLIGHT SCHEDULE
Direct Flights:
Sun 07:20 Midway, Chicago (MDW) 10:00 Oakland (OAK) 2 Southwest Airlines WN 143 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Operates only on 2025-11-30
Sun 21:30 Midway, Chicago (MDW) 00:05 Oakland (OAK) 2 Southwest Airlines WN 256 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-06-08 through 2025-08-03 The flight arrives 1 day after departure.
Mon,Thu,Fri 21:10 Midway, Chicago (MDW) 23:45 Oakland (OAK) 2 Southwest Airlines WN 261 Non-stop Boeing 737-700 (73W) 4:35 Valid until 2025-06-02
Sat 14:05 Midway, Chicago (MDW) 16:45 Oakland (OAK) 2 Southwest Airlines WN 494 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-11-08 through 2025-11-15
Sat 14:05 Midway, Chicago (MDW) 16:45 Oakland (OAK) 2 Southwest Airlines WN 494 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-12-06 through 2025-12-13
Tue,Wed 16:05 Midway, Chicago (MDW) 18:40 Oakland (OAK) 2 Southwest Airlines WN 494 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-11-04 through 2025-11-12
Mon-Thu 16:05 Midway, Chicago (MDW) 18:40 Oakland (OAK) 2 Southwest Airlines WN 494 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-11-17 through 2025-11-20
Mon-Fri 16:05 Midway, Chicago (MDW) 18:40 Oakland (OAK) 2 Southwest Airlines WN 494 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-12-02 through 2025-12-11
Mon-Wed 16:05 Midway, Chicago (MDW) 18:40 Oakland (OAK) 2 Southwest Airlines WN 494 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-12-15 through 2025-12-17
Wed,Thu 16:05 Midway, Chicago (MDW) 18:40 Oakland (OAK) 2 Southwest Airlines WN 494 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-12-24 through 2026-01-01
Thu 08:25 Midway, Chicago (MDW) 11:10 Oakland (OAK) 2 Southwest Airlines WN 1036 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Operates only on 2025-11-27
Sat 08:45 Midway, Chicago (MDW) 11:30 Oakland (OAK) 2 Southwest Airlines WN 1517 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2025-11-22 through 2025-11-29
Sat 08:45 Midway, Chicago (MDW) 11:30 Oakland (OAK) 2 Southwest Airlines WN 1517 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2025-12-20 through 2026-01-03
Mon,Thu,Fri,Sun 07:45 Midway, Chicago (MDW) 10:25 Oakland (OAK) 2 Southwest Airlines WN 1700 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 07:45 Midway, Chicago (MDW) 10:25 Oakland (OAK) 2 Southwest Airlines WN 1700 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-11-21 through 2025-11-28
Fri,Sun 07:45 Midway, Chicago (MDW) 10:25 Oakland (OAK) 2 Southwest Airlines WN 1700 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-12-07 through 2025-12-14
Thu 07:45 Midway, Chicago (MDW) 10:25 Oakland (OAK) 2 Southwest Airlines WN 1700 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Operates only on 2025-12-18
Mon 07:45 Midway, Chicago (MDW) 10:25 Oakland (OAK) 2 Southwest Airlines WN 1700 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Operates only on 2026-01-05
Sat 22:50 Midway, Chicago (MDW) 01:30 Oakland (OAK) 2 Southwest Airlines WN 2218 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-11-22 through 2025-11-29 The flight arrives 1 day after departure.
Sat 22:50 Midway, Chicago (MDW) 01:30 Oakland (OAK) 2 Southwest Airlines WN 2218 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-12-20 through 2026-01-03 The flight arrives 1 day after departure.
Sun 09:35 Midway, Chicago (MDW) 12:05 Oakland (OAK) 2 Southwest Airlines WN 2305 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Operates only on 2025-08-31
Sun 17:35 Midway, Chicago (MDW) 20:10 Oakland (OAK) 2 Southwest Airlines WN 2341 Non-stop Boeing 737-700 (73W) 4:35 Operates only on 2025-05-25
Mon-Wed 07:45 Midway, Chicago (MDW) 10:25 Oakland (OAK) 2 Southwest Airlines WN 2376 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 07:45 Midway, Chicago (MDW) 10:25 Oakland (OAK) 2 Southwest Airlines WN 2376 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2025-12-19 through 2026-01-04
Mon,Thu,Fri 07:45 Midway, Chicago (MDW) 10:15 Oakland (OAK) 2 Southwest Airlines WN 2449 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-10-02 through 2025-10-31
Sun 08:10 Midway, Chicago (MDW) 10:45 Oakland (OAK) 2 Southwest Airlines WN 2449 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-10-05 through 2025-10-26
Sat 15:55 Midway, Chicago (MDW) 18:30 Oakland (OAK) 2 Southwest Airlines WN 2449 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-10-04 through 2025-11-01
Tue,Wed 16:15 Midway, Chicago (MDW) 18:50 Oakland (OAK) 2 Southwest Airlines WN 2449 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-10-07 through 2025-10-29
Sun 12:50 Midway, Chicago (MDW) 15:25 Oakland (OAK) 2 Southwest Airlines WN 2937 Non-stop Boeing 737-700 (73W) 4:35 Valid until 2025-05-18
Sun 12:50 Midway, Chicago (MDW) 15:25 Oakland (OAK) 2 Southwest Airlines WN 2937 Non-stop Boeing 737-700 (73W) 4:35 Operates only on 2025-06-01
Tue,Wed,Sat 16:55 Midway, Chicago (MDW) 19:30 Oakland (OAK) 2 Southwest Airlines WN 2937 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Valid until 2025-06-04
Tue,Wed 15:00 Midway, Chicago (MDW) 17:30 Oakland (OAK) 2 Southwest Airlines WN 3338 Non-stop Boeing 737-700 (73W) 4:30 Effective 2025-08-05 through 2025-10-01
Sun 08:20 Midway, Chicago (MDW) 10:50 Oakland (OAK) 2 Southwest Airlines WN 3360 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-08-10 through 2025-08-24
Sun 08:20 Midway, Chicago (MDW) 10:50 Oakland (OAK) 2 Southwest Airlines WN 3360 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-09-07 through 2025-09-28
Sun 19:50 Midway, Chicago (MDW) 22:20 Oakland (OAK) 2 Southwest Airlines WN 3416 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-10-05 through 2025-10-26
Mon,Thu,Fri 07:20 Midway, Chicago (MDW) 09:50 Oakland (OAK) 2 Southwest Airlines WN 3643 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 07:20 Midway, Chicago (MDW) 09:50 Oakland (OAK) 2 Southwest Airlines WN 3643 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-07-07 through 2025-08-04
Sun 08:05 Midway, Chicago (MDW) 10:35 Oakland (OAK) 2 Southwest Airlines WN 3643 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-06-08 through 2025-08-03
Fri 16:00 Midway, Chicago (MDW) 18:30 Oakland (OAK) 2 Southwest Airlines WN 3643 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Operates only on 2025-07-04
Tue,Wed 16:50 Midway, Chicago (MDW) 19:20 Oakland (OAK) 2 Southwest Airlines WN 3643 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-06-10 through 2025-07-30
Sat 17:45 Midway, Chicago (MDW) 20:20 Oakland (OAK) 2 Southwest Airlines WN 3643 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-06-07 through 2025-08-02
Mon,Thu,Fri 13:15 Midway, Chicago (MDW) 15:45 Oakland (OAK) 2 Southwest Airlines WN 3725 Non-stop Boeing 737-700 (73W) 4:30 Effective 2025-08-07 through 2025-09-29
Sat 15:25 Midway, Chicago (MDW) 17:55 Oakland (OAK) 2 Southwest Airlines WN 3725 Non-stop Boeing 737-700 (73W) 4:30 Effective 2025-08-09 through 2025-09-27
Sun 16:35 Midway, Chicago (MDW) 19:05 Oakland (OAK) 2 Southwest Airlines WN 3725 Non-stop Boeing 737-700 (73W) 4:30 Operates only on 2025-08-31
Sun 20:20 Midway, Chicago (MDW) 22:55 Oakland (OAK) 2 Southwest Airlines WN 3725 Non-stop Boeing 737-700 (73W) 4:35 Effective 2025-08-10 through 2025-08-24
Sun 20:20 Midway, Chicago (MDW) 22:55 Oakland (OAK) 2 Southwest Airlines WN 3725 Non-stop Boeing 737-700 (73W) 4:35 Effective 2025-09-07 through 2025-09-28
Sun 20:25 Midway, Chicago (MDW) 23:05 Oakland (OAK) 2 Southwest Airlines WN 4972 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Operates only on 2025-11-30
Non-Direct Flights:
Mon,Thu,Fri 18:50 Midway, Chicago (MDW) 22:55 Oakland (OAK) 2 Southwest Airlines WN 187 1-stop Boeing 737 MAX 8 (7M8) 6:05 Effective 2025-10-02 through 2025-10-31
Tue,Wed 15:15 Midway, Chicago (MDW) 20:45 Oakland (OAK) 2 Southwest Airlines WN 223 1-stop Boeing 737 MAX 8 (7M8) 7:30 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 14:20 Midway, Chicago (MDW) 19:30 Oakland (OAK) 2 Southwest Airlines WN 311 1-stop Boeing 737-700 (73W) 7:10 Effective 2025-08-07 through 2025-09-29

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Parallax here MDW-OAK

1 2

A domestic route departing from the Midway, Chicago 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 4:30 and 4:45.

Return (OAK-MDW) flights

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

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FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN143

07:20

Midway, Chicago (MDW)

10:00

Oakland (OAK) 2

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN256

21:30

Midway, Chicago (MDW)

00:05(+1)

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN261

21:10

Midway, Chicago (MDW)

23:45

Oakland (OAK) 2

Valid until 2025-06-02

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN494

14:05

Midway, Chicago (MDW)

16:45

Oakland (OAK) 2

Effective 2025-11-08 through 2025-11-15

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN494

14:05

Midway, Chicago (MDW)

16:45

Oakland (OAK) 2

Effective 2025-12-06 through 2025-12-13

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN494

16:05

Midway, Chicago (MDW)

18:40

Oakland (OAK) 2

Effective 2025-11-04 through 2025-11-12

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN494

16:05

Midway, Chicago (MDW)

18:40

Oakland (OAK) 2

Effective 2025-11-17 through 2025-11-20

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN494

16:05

Midway, Chicago (MDW)

18:40

Oakland (OAK) 2

Effective 2025-12-02 through 2025-12-11

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN494

16:05

Midway, Chicago (MDW)

18:40

Oakland (OAK) 2

Effective 2025-12-15 through 2025-12-17

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN494

16:05

Midway, Chicago (MDW)

18:40

Oakland (OAK) 2

Effective 2025-12-24 through 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1036

08:25

Midway, Chicago (MDW)

11:10

Oakland (OAK) 2

Operates only on 2025-11-27

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1517

08:45

Midway, Chicago (MDW)

11:30

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1517

08:45

Midway, Chicago (MDW)

11:30

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:45, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1700

07:45

Midway, Chicago (MDW)

10:25

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1700

07:45

Midway, Chicago (MDW)

10:25

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1700

07:45

Midway, Chicago (MDW)

10:25

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1700

07:45

Midway, Chicago (MDW)

10:25

Oakland (OAK) 2

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1700

07:45

Midway, Chicago (MDW)

10:25

Oakland (OAK) 2

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2218

22:50

Midway, Chicago (MDW)

01:30(+1)

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2218

22:50

Midway, Chicago (MDW)

01:30(+1)

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2305

09:35

Midway, Chicago (MDW)

12:05

Oakland (OAK) 2

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2341

17:35

Midway, Chicago (MDW)

20:10

Oakland (OAK) 2

Operates only on 2025-05-25

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2376

07:45

Midway, Chicago (MDW)

10:25

Oakland (OAK) 2

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2376

07:45

Midway, Chicago (MDW)

10:25

Oakland (OAK) 2

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

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2449

07:45

Midway, Chicago (MDW)

10:15

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2449

08:10

Midway, Chicago (MDW)

10:45

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2449

15:55

Midway, Chicago (MDW)

18:30

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2449

16:15

Midway, Chicago (MDW)

18:50

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2937

12:50

Midway, Chicago (MDW)

15:25

Oakland (OAK) 2

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2937

12:50

Midway, Chicago (MDW)

15:25

Oakland (OAK) 2

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2937

16:55

Midway, Chicago (MDW)

19:30

Oakland (OAK) 2

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3338

15:00

Midway, Chicago (MDW)

17:30

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3360

08:20

Midway, Chicago (MDW)

10:50

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3360

08:20

Midway, Chicago (MDW)

10:50

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3416

19:50

Midway, Chicago (MDW)

22:20

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3643

07:20

Midway, Chicago (MDW)

09:50

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3643

07:20

Midway, Chicago (MDW)

09:50

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3643

08:05

Midway, Chicago (MDW)

10:35

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3643

16:00

Midway, Chicago (MDW)

18:30

Oakland (OAK) 2

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3643

16:50

Midway, Chicago (MDW)

19:20

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3643

17:45

Midway, Chicago (MDW)

20:20

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3725

13:15

Midway, Chicago (MDW)

15:45

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3725

15:25

Midway, Chicago (MDW)

17:55

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:30, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3725

16:35

Midway, Chicago (MDW)

19:05

Oakland (OAK) 2

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3725

20:20

Midway, Chicago (MDW)

22:55

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3725

20:20

Midway, Chicago (MDW)

22:55

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN4972

20:25

Midway, Chicago (MDW)

23:05

Oakland (OAK) 2

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:40, non-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN187

18:50

Midway, Chicago (MDW)

22:55

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:05, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN223

15:15

Midway, Chicago (MDW)

20:45

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN311

14:20

Midway, Chicago (MDW)

19:30

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 7:10, 1-stop
Boeing 737-700 (73W)

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A domestic route departing from the Midway, Chicago 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 4:30 and 4:45.

Return (OAK-MDW) flights

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