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

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FLIGHT SCHEDULE
Direct Flights:
Sat 13:30 Oakland (OAK) 2 19:30 Midway, Chicago (MDW) Southwest Airlines WN 174 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-11-22 through 2025-11-29
Sat 13:30 Oakland (OAK) 2 19:30 Midway, Chicago (MDW) Southwest Airlines WN 174 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-12-20 through 2026-01-03
Mon,Thu,Fri 05:05 Oakland (OAK) 2 11:15 Midway, Chicago (MDW) Southwest Airlines WN 189 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Valid until 2025-06-02
Tue,Wed 05:50 Oakland (OAK) 2 12:00 Midway, Chicago (MDW) Southwest Airlines WN 189 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Valid until 2025-06-04
Sun 05:55 Oakland (OAK) 2 12:05 Midway, Chicago (MDW) Southwest Airlines WN 189 Non-stop Boeing 737-800 (73H) 4:10 Valid until 2025-05-18
Sun 05:55 Oakland (OAK) 2 12:05 Midway, Chicago (MDW) Southwest Airlines WN 189 Non-stop Boeing 737-800 (73H) 4:10 Operates only on 2025-06-01
Sat 06:05 Oakland (OAK) 2 12:15 Midway, Chicago (MDW) Southwest Airlines WN 189 Non-stop Boeing 737-700 (73W) 4:10 Valid until 2025-05-24
Sat,Sun 06:05 Oakland (OAK) 2 12:15 Midway, Chicago (MDW) Southwest Airlines WN 189 Non-stop Boeing 737-700 (73W) 4:10 Effective 2025-05-25 through 2025-05-31
Sat 05:10 Oakland (OAK) 2 11:15 Midway, Chicago (MDW) Southwest Airlines WN 199 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-11-22 through 2025-11-29
Sat 05:10 Oakland (OAK) 2 11:15 Midway, Chicago (MDW) Southwest Airlines WN 199 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-12-20 through 2026-01-03
Sun 08:15 Oakland (OAK) 2 14:20 Midway, Chicago (MDW) Southwest Airlines WN 532 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2025-08-31
Mon,Thu,Fri 05:55 Oakland (OAK) 2 12:05 Midway, Chicago (MDW) Southwest Airlines WN 585 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 05:55 Oakland (OAK) 2 12:05 Midway, Chicago (MDW) Southwest Airlines WN 585 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2025-07-07 through 2025-08-04
Sat 06:15 Oakland (OAK) 2 12:25 Midway, Chicago (MDW) Southwest Airlines WN 585 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2025-06-07 through 2025-08-02
Sun 06:20 Oakland (OAK) 2 12:30 Midway, Chicago (MDW) Southwest Airlines WN 585 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2025-06-08 through 2025-08-03
Fri 07:40 Oakland (OAK) 2 13:45 Midway, Chicago (MDW) Southwest Airlines WN 585 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2025-07-04
Tue,Wed 12:05 Oakland (OAK) 2 18:10 Midway, Chicago (MDW) Southwest Airlines WN 585 Non-stop Boeing 737-800 (73H) 4:05 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 05:50 Oakland (OAK) 2 11:55 Midway, Chicago (MDW) Southwest Airlines WN 1218 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-10-02 through 2025-10-31
Tue,Wed 05:50 Oakland (OAK) 2 11:55 Midway, Chicago (MDW) Southwest Airlines WN 1218 Non-stop Boeing 737-800 (73H) 4:05 Effective 2025-10-07 through 2025-10-29
Sun 06:40 Oakland (OAK) 2 12:45 Midway, Chicago (MDW) Southwest Airlines WN 1218 Non-stop Boeing 737-800 (73H) 4:05 Effective 2025-10-05 through 2025-10-26
Mon,Thu,Fri,Sun 05:25 Oakland (OAK) 2 11:30 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-800 (73H) 4:05 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 05:25 Oakland (OAK) 2 11:30 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-800 (73H) 4:05 Effective 2025-11-21 through 2025-11-28
Fri,Sun 05:25 Oakland (OAK) 2 11:30 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-800 (73H) 4:05 Effective 2025-12-07 through 2025-12-14
Thu 05:25 Oakland (OAK) 2 11:30 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2025-12-18
Mon 05:25 Oakland (OAK) 2 11:30 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2026-01-05
Sun 05:30 Oakland (OAK) 2 11:35 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2025-11-30
Sat 10:15 Oakland (OAK) 2 16:20 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-800 (73H) 4:05 Effective 2025-11-08 through 2025-11-15
Sat 10:15 Oakland (OAK) 2 16:20 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-800 (73H) 4:05 Effective 2025-12-06 through 2025-12-13
Tue,Wed 11:00 Oakland (OAK) 2 17:05 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-11-04 through 2025-11-12
Mon-Thu 11:00 Oakland (OAK) 2 17:05 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-11-17 through 2025-11-20
Mon-Fri 11:00 Oakland (OAK) 2 17:05 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-12-02 through 2025-12-11
Mon-Wed 11:00 Oakland (OAK) 2 17:05 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-12-15 through 2025-12-17
Wed,Thu 11:00 Oakland (OAK) 2 17:05 Midway, Chicago (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-12-24 through 2026-01-01
Thu 06:40 Oakland (OAK) 2 12:45 Midway, Chicago (MDW) Southwest Airlines WN 2374 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2025-11-27
Sun 10:50 Oakland (OAK) 2 16:55 Midway, Chicago (MDW) Southwest Airlines WN 2853 Non-stop Boeing 737-700 (73W) 4:05 Operates only on 2025-08-31
Sun 13:15 Oakland (OAK) 2 19:15 Midway, Chicago (MDW) Southwest Airlines WN 2853 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-08-10 through 2025-08-24
Sun 13:15 Oakland (OAK) 2 19:15 Midway, Chicago (MDW) Southwest Airlines WN 2853 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-09-07 through 2025-09-28
Sat 09:05 Oakland (OAK) 2 15:15 Midway, Chicago (MDW) Southwest Airlines WN 2989 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2025-10-04 through 2025-11-01
Sun 15:10 Oakland (OAK) 2 21:10 Midway, Chicago (MDW) Southwest Airlines WN 3105 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-06-08 through 2025-08-03
Mon,Thu,Fri 05:15 Oakland (OAK) 2 11:20 Midway, Chicago (MDW) Southwest Airlines WN 3123 Non-stop Boeing 737-800 (73H) 4:05 Effective 2025-08-07 through 2025-09-29
Sun 05:50 Oakland (OAK) 2 11:55 Midway, Chicago (MDW) Southwest Airlines WN 3123 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-08-10 through 2025-08-24
Sun 05:50 Oakland (OAK) 2 11:55 Midway, Chicago (MDW) Southwest Airlines WN 3123 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-09-07 through 2025-09-28
Sat 09:05 Oakland (OAK) 2 15:10 Midway, Chicago (MDW) Southwest Airlines WN 3123 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-08-09 through 2025-09-27
Tue,Wed 11:00 Oakland (OAK) 2 17:05 Midway, Chicago (MDW) Southwest Airlines WN 3123 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-08-05 through 2025-10-01
Sun 13:10 Oakland (OAK) 2 19:15 Midway, Chicago (MDW) Southwest Airlines WN 3350 Non-stop Boeing 737-800 (73H) 4:05 Effective 2025-10-05 through 2025-10-26
Mon-Wed 05:35 Oakland (OAK) 2 11:40 Midway, Chicago (MDW) Southwest Airlines WN 3808 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 05:35 Oakland (OAK) 2 11:40 Midway, Chicago (MDW) Southwest Airlines WN 3808 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-12-19 through 2026-01-04
Sun 13:40 Oakland (OAK) 2 19:40 Midway, Chicago (MDW) Southwest Airlines WN 4171 Non-stop Boeing 737-800 (73H) 4:00 Operates only on 2025-11-30
Non-Direct Flights:
Tue,Wed 09:20 Oakland (OAK) 2 17:05 Midway, Chicago (MDW) Southwest Airlines WN 143 1-stop Boeing 737-700 (Scimitar Winglets) 5:45 Effective 2025-11-04 through 2025-11-12
Mon-Thu 09:20 Oakland (OAK) 2 17:05 Midway, Chicago (MDW) Southwest Airlines WN 143 1-stop Boeing 737-700 (Scimitar Winglets) 5:45 Effective 2025-11-17 through 2025-11-20

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Parallax here OAK-MDW

1 2

A domestic route departing from the Oakland airport (OAK) and arriving at Midway, Chicago airport (MDW).
The flight distance is 1839 miles, or 2959 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 4:00 and 4:10.

Return (MDW-OAK) flights

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

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FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN174

13:30

Oakland (OAK) 2

19:30

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN174

13:30

Oakland (OAK) 2

19:30

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN189

05:05

Oakland (OAK) 2

11:15

Midway, Chicago (MDW)

Valid until 2025-06-02

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN189

05:50

Oakland (OAK) 2

12:00

Midway, Chicago (MDW)

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN189

05:55

Oakland (OAK) 2

12:05

Midway, Chicago (MDW)

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:10, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN189

05:55

Oakland (OAK) 2

12:05

Midway, Chicago (MDW)

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:10, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN189

06:05

Oakland (OAK) 2

12:15

Midway, Chicago (MDW)

Valid until 2025-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:10, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN189

06:05

Oakland (OAK) 2

12:15

Midway, Chicago (MDW)

Effective 2025-05-25 through 2025-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun

Duration: 4:10, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN199

05:10

Oakland (OAK) 2

11:15

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN199

05:10

Oakland (OAK) 2

11:15

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN532

08:15

Oakland (OAK) 2

14:20

Midway, Chicago (MDW)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN585

05:55

Oakland (OAK) 2

12:05

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN585

05:55

Oakland (OAK) 2

12:05

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN585

06:15

Oakland (OAK) 2

12:25

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN585

06:20

Oakland (OAK) 2

12:30

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN585

07:40

Oakland (OAK) 2

13:45

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

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

Southwest Airlines WN585

12:05

Oakland (OAK) 2

18:10

Midway, Chicago (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN1218

05:50

Oakland (OAK) 2

11:55

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN1218

05:50

Oakland (OAK) 2

11:55

Midway, Chicago (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN1218

06:40

Oakland (OAK) 2

12:45

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2363

05:25

Oakland (OAK) 2

11:30

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Southwest Airlines WN2363

05:25

Oakland (OAK) 2

11:30

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN2363

05:25

Oakland (OAK) 2

11:30

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN2363

05:25

Oakland (OAK) 2

11:30

Midway, Chicago (MDW)

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2363

05:25

Oakland (OAK) 2

11:30

Midway, Chicago (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2363

05:30

Oakland (OAK) 2

11:35

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2363

10:15

Oakland (OAK) 2

16:20

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2363

10:15

Oakland (OAK) 2

16:20

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2363

11:00

Oakland (OAK) 2

17:05

Midway, Chicago (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2363

11:00

Oakland (OAK) 2

17:05

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2363

11:00

Oakland (OAK) 2

17:05

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN2363

11:00

Oakland (OAK) 2

17:05

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2363

11:00

Oakland (OAK) 2

17:05

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2374

06:40

Oakland (OAK) 2

12:45

Midway, Chicago (MDW)

Operates only on 2025-11-27

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2853

10:50

Oakland (OAK) 2

16:55

Midway, Chicago (MDW)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:05, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2853

13:15

Oakland (OAK) 2

19:15

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2853

13:15

Oakland (OAK) 2

19:15

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2989

09:05

Oakland (OAK) 2

15:15

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3105

15:10

Oakland (OAK) 2

21:10

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN3123

05:15

Oakland (OAK) 2

11:20

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN3123

05:50

Oakland (OAK) 2

11:55

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN3123

05:50

Oakland (OAK) 2

11:55

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN3123

09:05

Oakland (OAK) 2

15:10

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN3123

11:00

Oakland (OAK) 2

17:05

Midway, Chicago (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN3350

13:10

Oakland (OAK) 2

19:15

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN3808

05:35

Oakland (OAK) 2

11:40

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN3808

05:35

Oakland (OAK) 2

11:40

Midway, Chicago (MDW)

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

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN4171

13:40

Oakland (OAK) 2

19:40

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN143

09:20

Oakland (OAK) 2

17:05

Midway, Chicago (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN143

09:20

Oakland (OAK) 2

17:05

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 5:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

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A domestic route departing from the Oakland airport (OAK) and arriving at Midway, Chicago airport (MDW).
The flight distance is 1839 miles, or 2959 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 4:00 and 4:10.

Return (MDW-OAK) flights

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