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

FLIGHT SCHEDULE
Direct Flights:
Sun 11:05 Chicago Midway (MDW) 13:40 Oakland (OAK) 2 Southwest Airlines WN 186 Non-stop Boeing 737-700 (Scimitar Winglets) 4:35 Operates only on 2026-05-24
Tue,Wed 10:00 Chicago Midway (MDW) 12:35 Oakland (OAK) 2 Southwest Airlines WN 192 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-04-07 through 2026-06-03
Sat 20:55 Chicago Midway (MDW) 23:50 Oakland (OAK) 2 Southwest Airlines WN 470 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-02-14 through 2026-02-28
Wed,Thu 16:05 Chicago Midway (MDW) 18:40 Oakland (OAK) 2 Southwest Airlines WN 494 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Valid until 2026-01-01
Mon,Thu,Fri 07:55 Chicago Midway (MDW) 10:50 Oakland (OAK) 2 Southwest Airlines WN 1369 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 07:55 Chicago Midway (MDW) 10:50 Oakland (OAK) 2 Southwest Airlines WN 1369 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-02-20 through 2026-03-01
Mon-Fri 11:10 Chicago Midway (MDW) 14:05 Oakland (OAK) 2 Southwest Airlines WN 1371 Non-stop Boeing 737-700 (Scimitar Winglets) 4:55 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 11:10 Chicago Midway (MDW) 14:05 Oakland (OAK) 2 Southwest Airlines WN 1371 Non-stop Boeing 737-700 (Scimitar Winglets) 4:55 Effective 2026-01-18 through 2026-01-23
Mon-Fri 11:10 Chicago Midway (MDW) 14:05 Oakland (OAK) 2 Southwest Airlines WN 1371 Non-stop Boeing 737-700 (Scimitar Winglets) 4:55 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 11:10 Chicago Midway (MDW) 14:05 Oakland (OAK) 2 Southwest Airlines WN 1371 Non-stop Boeing 737-700 (Scimitar Winglets) 4:55 Effective 2026-02-08 through 2026-02-11
Tue,Wed 11:10 Chicago Midway (MDW) 14:05 Oakland (OAK) 2 Southwest Airlines WN 1371 Non-stop Boeing 737-700 (Scimitar Winglets) 4:55 Effective 2026-02-18 through 2026-03-04
Tue,Wed 21:00 Chicago Midway (MDW) 23:40 Oakland (OAK) 2 Southwest Airlines WN 1394 Non-stop Boeing 737-700 (Scimitar Winglets) 4:40 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 21:30 Chicago Midway (MDW) 00:10 Oakland (OAK) 2 Southwest Airlines WN 1394 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2026-03-05 through 2026-04-06 The flight arrives 1 day after departure.
Sat 21:40 Chicago Midway (MDW) 00:20 Oakland (OAK) 2 Southwest Airlines WN 1394 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2026-03-14 through 2026-04-04 The flight arrives 1 day after departure.
Mon-Fri 20:35 Chicago Midway (MDW) 23:05 Oakland (OAK) 2 Southwest Airlines WN 1413 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-08-04 through 2026-09-30
Tue,Wed 21:00 Chicago Midway (MDW) 23:30 Oakland (OAK) 2 Southwest Airlines WN 1447 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-06-09 through 2026-07-29
Sat 08:45 Chicago Midway (MDW) 11:30 Oakland (OAK) 2 Southwest Airlines WN 1517 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Valid until 2026-01-03
Mon 07:45 Chicago Midway (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
Sun 09:55 Chicago Midway (MDW) 12:30 Oakland (OAK) 2 Southwest Airlines WN 1743 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-04-12 through 2026-05-17
Sun 09:55 Chicago Midway (MDW) 12:30 Oakland (OAK) 2 Southwest Airlines WN 1743 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Operates only on 2026-05-31
Mon,Thu,Fri 10:05 Chicago Midway (MDW) 12:40 Oakland (OAK) 2 Southwest Airlines WN 1743 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-04-09 through 2026-06-01
Sat 17:55 Chicago Midway (MDW) 20:30 Oakland (OAK) 2 Southwest Airlines WN 1743 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-04-11 through 2026-05-30
Tue,Wed 20:50 Chicago Midway (MDW) 23:25 Oakland (OAK) 2 Southwest Airlines WN 1743 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 21:50 Chicago Midway (MDW) 00:25 Oakland (OAK) 2 Southwest Airlines WN 1748 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-04-09 through 2026-06-01 The flight arrives 1 day after departure.
Sat 13:20 Chicago Midway (MDW) 15:50 Oakland (OAK) 2 Southwest Airlines WN 2221 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-06-06 through 2026-08-01
Mon,Tue,Fri,Sun 07:50 Chicago Midway (MDW) 10:35 Oakland (OAK) 2 Southwest Airlines WN 2376 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Valid until 2026-01-04
Sun 09:55 Chicago Midway (MDW) 12:40 Oakland (OAK) 2 Southwest Airlines WN 2484 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2026-03-08 through 2026-04-05
Tue,Wed 10:00 Chicago Midway (MDW) 12:45 Oakland (OAK) 2 Southwest Airlines WN 2484 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2026-03-10 through 2026-04-01
Mon,Thu-Sat 10:05 Chicago Midway (MDW) 12:50 Oakland (OAK) 2 Southwest Airlines WN 2484 Non-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2026-03-05 through 2026-04-06
Mon-Fri 10:15 Chicago Midway (MDW) 12:40 Oakland (OAK) 2 Southwest Airlines WN 2779 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-08-04 through 2026-09-30
Sun 10:45 Chicago Midway (MDW) 13:15 Oakland (OAK) 2 Southwest Airlines WN 2779 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-08-09 through 2026-09-27
Sat 13:55 Chicago Midway (MDW) 16:20 Oakland (OAK) 2 Southwest Airlines WN 2779 Non-stop Boeing 737-700 (Scimitar Winglets) 4:25 Effective 2026-08-08 through 2026-09-26
Thu,Fri,Sun 08:10 Chicago Midway (MDW) 11:05 Oakland (OAK) 2 Southwest Airlines WN 2977 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-01-11 through 2026-01-16
Mon,Sun 08:10 Chicago Midway (MDW) 11:05 Oakland (OAK) 2 Southwest Airlines WN 2977 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 08:10 Chicago Midway (MDW) 11:05 Oakland (OAK) 2 Southwest Airlines WN 2977 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-02-01 through 2026-02-06
Mon,Sun 08:10 Chicago Midway (MDW) 11:05 Oakland (OAK) 2 Southwest Airlines WN 2977 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 08:10 Chicago Midway (MDW) 11:05 Oakland (OAK) 2 Southwest Airlines WN 2977 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-02-17 through 2026-02-23
Mon 08:10 Chicago Midway (MDW) 11:05 Oakland (OAK) 2 Southwest Airlines WN 2977 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Operates only on 2026-03-02
Sat 19:40 Chicago Midway (MDW) 22:35 Oakland (OAK) 2 Southwest Airlines WN 3055 Non-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-01-10 through 2026-02-07
Sat 22:50 Chicago Midway (MDW) 01:30 Oakland (OAK) 2 Southwest Airlines WN 3213 Non-stop Boeing 737-700 (Scimitar Winglets) 4:40 Operates only on 2026-01-03 The flight arrives 1 day after departure.
Tue,Wed,Sun 10:00 Chicago Midway (MDW) 12:30 Oakland (OAK) 2 Southwest Airlines WN 3366 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 10:10 Chicago Midway (MDW) 12:40 Oakland (OAK) 2 Southwest Airlines WN 3366 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-06-04 through 2026-08-03
Sun 20:25 Chicago Midway (MDW) 22:55 Oakland (OAK) 2 Southwest Airlines WN 3461 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-08-09 through 2026-09-27
Sat 21:40 Chicago Midway (MDW) 00:20 Oakland (OAK) 2 Southwest Airlines WN 3480 Non-stop Boeing 737 MAX 8 (7M8) 4:40 Operates only on 2026-03-07 The flight arrives 1 day after departure.
Sun 21:25 Chicago Midway (MDW) 23:55 Oakland (OAK) 2 Southwest Airlines WN 4042 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 21:40 Chicago Midway (MDW) 00:10 Oakland (OAK) 2 Southwest Airlines WN 4042 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-06-04 through 2026-08-03 The flight arrives 1 day after departure.
Non-Direct Flights:
Mon,Thu,Fri 13:35 Chicago Midway (MDW) 18:15 Oakland (OAK) 2 Southwest Airlines WN 313 1-stop Boeing 737 MAX 8 (7M8) 6:40 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 13:35 Chicago Midway (MDW) 18:15 Oakland (OAK) 2 Southwest Airlines WN 313 1-stop Boeing 737 MAX 8 (7M8) 6:40 Effective 2026-02-20 through 2026-03-01
Sat 19:00 Chicago Midway (MDW) 00:25 Oakland (OAK) 2 Southwest Airlines WN 429 1-stop Boeing 737 MAX 8 (7M8) 7:25 Valid until 2026-01-03 The flight arrives 1 day after departure.
Sat 14:15 Chicago Midway (MDW) 19:05 Oakland (OAK) 2 Southwest Airlines WN 519 1-stop Boeing 737-700 (Scimitar Winglets) 6:50 Operates only on 2026-01-03

1 2

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

Direct Flights:

Southwest Airlines WN186

11:05

Chicago Midway (MDW)

13:40

Oakland (OAK) 2

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN192

10:00

Chicago Midway (MDW)

12:35

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN470

20:55

Chicago Midway (MDW)

23:50

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN494

16:05

Chicago Midway (MDW)

18:40

Oakland (OAK) 2

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1369

07:55

Chicago Midway (MDW)

10:50

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1369

07:55

Chicago Midway (MDW)

10:50

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1371

11:10

Chicago Midway (MDW)

14:05

Oakland (OAK) 2

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 4:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1371

11:10

Chicago Midway (MDW)

14:05

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu

Fri

Sat
-

Sun

Duration: 4:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1371

11:10

Chicago Midway (MDW)

14:05

Oakland (OAK) 2

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 4:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1371

11:10

Chicago Midway (MDW)

14:05

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1371

11:10

Chicago Midway (MDW)

14:05

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1394

21:00

Chicago Midway (MDW)

23:40

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1394

21:30

Chicago Midway (MDW)

00:10(+1)

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1394

21:40

Chicago Midway (MDW)

00:20(+1)

Oakland (OAK) 2

Effective 2026-03-14 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1413

20:35

Chicago Midway (MDW)

23:05

Oakland (OAK) 2

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1447

21:00

Chicago Midway (MDW)

23:30

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1517

08:45

Chicago Midway (MDW)

11:30

Oakland (OAK) 2

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1700

07:45

Chicago Midway (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)

Direct Flights:

Southwest Airlines WN1743

09:55

Chicago Midway (MDW)

12:30

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1743

09:55

Chicago Midway (MDW)

12:30

Oakland (OAK) 2

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1743

10:05

Chicago Midway (MDW)

12:40

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1743

17:55

Chicago Midway (MDW)

20:30

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1743

20:50

Chicago Midway (MDW)

23:25

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1748

21:50

Chicago Midway (MDW)

00:25(+1)

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2221

13:20

Chicago Midway (MDW)

15:50

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN2376

07:50

Chicago Midway (MDW)

10:35

Oakland (OAK) 2

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2484

09:55

Chicago Midway (MDW)

12:40

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2484

10:00

Chicago Midway (MDW)

12:45

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2484

10:05

Chicago Midway (MDW)

12:50

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN2779

10:15

Chicago Midway (MDW)

12:40

Oakland (OAK) 2

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2779

10:45

Chicago Midway (MDW)

13:15

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2779

13:55

Chicago Midway (MDW)

16:20

Oakland (OAK) 2

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2977

08:10

Chicago Midway (MDW)

11:05

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2977

08:10

Chicago Midway (MDW)

11:05

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2977

08:10

Chicago Midway (MDW)

11:05

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2977

08:10

Chicago Midway (MDW)

11:05

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2977

08:10

Chicago Midway (MDW)

11:05

Oakland (OAK) 2

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

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2977

08:10

Chicago Midway (MDW)

11:05

Oakland (OAK) 2

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3055

19:40

Chicago Midway (MDW)

22:35

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3213

22:50

Chicago Midway (MDW)

01:30(+1)

Oakland (OAK) 2

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:40, non-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3366

10:00

Chicago Midway (MDW)

12:30

Oakland (OAK) 2

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN3366

10:10

Chicago Midway (MDW)

12:40

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN3461

20:25

Chicago Midway (MDW)

22:55

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN3480

21:40

Chicago Midway (MDW)

00:20(+1)

Oakland (OAK) 2

Operates only on 2026-03-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN4042

21:25

Chicago Midway (MDW)

23:55

Oakland (OAK) 2

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4042

21:40

Chicago Midway (MDW)

00:10(+1)

Oakland (OAK) 2

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Non-Direct Flights:

Southwest Airlines WN313

13:35

Chicago Midway (MDW)

18:15

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 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN313

13:35

Chicago Midway (MDW)

18:15

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 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN429

19:00

Chicago Midway (MDW)

00:25(+1)

Oakland (OAK) 2

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 7:25, 1-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Non-Direct Flights:

Southwest Airlines WN519

14:15

Chicago Midway (MDW)

19:05

Oakland (OAK) 2

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:50, 1-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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