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

FLIGHT SCHEDULE
Direct Flights:
Sat 13:30 Oakland (OAK) 2 19:30 Chicago Midway (MDW) Southwest Airlines WN 174 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Valid until 2026-01-03
Sat 05:10 Oakland (OAK) 2 11:15 Chicago Midway (MDW) Southwest Airlines WN 199 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Valid until 2026-01-03
Mon,Thu,Fri 05:25 Oakland (OAK) 2 11:30 Chicago Midway (MDW) Southwest Airlines WN 814 Non-stop Boeing 737-800 (73H) 4:05 Effective 2026-08-06 through 2026-09-28
Sat 05:40 Oakland (OAK) 2 11:40 Chicago Midway (MDW) Southwest Airlines WN 1150 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 05:45 Oakland (OAK) 2 11:45 Chicago Midway (MDW) Southwest Airlines WN 1150 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-03-05 through 2026-04-06
Tue,Wed 05:50 Oakland (OAK) 2 11:55 Chicago Midway (MDW) Southwest Airlines WN 1150 Non-stop Boeing 737-800 (73H) 4:05 Effective 2026-03-10 through 2026-04-01
Sun 05:05 Oakland (OAK) 2 11:10 Chicago Midway (MDW) Southwest Airlines WN 2211 Non-stop Boeing 737-800 (73H) 4:05 Effective 2026-06-07 through 2026-08-02
Mon 05:25 Oakland (OAK) 2 11:30 Chicago Midway (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2026-01-05
Wed,Thu 11:00 Oakland (OAK) 2 17:05 Chicago Midway (MDW) Southwest Airlines WN 2363 Non-stop Boeing 737-700 (73W) 4:05 Valid until 2026-01-01
Mon,Thu,Fri 05:10 Oakland (OAK) 2 11:15 Chicago Midway (MDW) Southwest Airlines WN 2744 Non-stop Boeing 737-800 (73H) 4:05 Effective 2026-06-04 through 2026-08-03
Tue,Wed 05:55 Oakland (OAK) 2 12:00 Chicago Midway (MDW) Southwest Airlines WN 2761 Non-stop Boeing 737-800 (73H) 4:05 Effective 2026-06-09 through 2026-07-29
Daily 23:55 Oakland (OAK) 2 05:55 Chicago Midway (MDW) Southwest Airlines WN 2986 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-08-04 through 2026-09-30 The flight arrives 1 day after departure.
Daily 23:55 Oakland (OAK) 2 06:00 Chicago Midway (MDW) Southwest Airlines WN 3059 Non-stop Boeing 737-800 (73H) 4:05 Effective 2026-06-04 through 2026-08-03 The flight arrives 1 day after departure.
Tue,Wed 05:50 Oakland (OAK) 2 11:55 Chicago Midway (MDW) Southwest Airlines WN 3551 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 05:55 Oakland (OAK) 2 12:00 Chicago Midway (MDW) Southwest Airlines WN 3551 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-04-09 through 2026-06-01
Daily 23:55 Oakland (OAK) 2 06:00 Chicago Midway (MDW) Southwest Airlines WN 3552 Non-stop Boeing 737-800 (73H) 4:05 Effective 2026-04-07 through 2026-06-03 The flight arrives 1 day after departure.
Mon,Tue,Fri,Sun 05:25 Oakland (OAK) 2 11:30 Chicago Midway (MDW) Southwest Airlines WN 3808 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Valid until 2026-01-04
Tue,Wed 10:35 Oakland (OAK) 2 16:35 Chicago Midway (MDW) Southwest Airlines WN 3816 Non-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-08-04 through 2026-09-30
Thu,Fri 23:55 Oakland (OAK) 2 05:55 Chicago Midway (MDW) Southwest Airlines WN 4069 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-03-05 through 2026-03-06 The flight arrives 1 day after departure.
Daily 23:55 Oakland (OAK) 2 05:55 Chicago Midway (MDW) Southwest Airlines WN 4069 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-03-08 through 2026-04-06 The flight arrives 1 day after departure.
Sat 05:55 Oakland (OAK) 2 12:00 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-01-10 through 2026-02-07
Thu,Fri,Sun 06:30 Oakland (OAK) 2 12:35 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-01-11 through 2026-01-16
Mon,Sun 06:30 Oakland (OAK) 2 12:35 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 06:30 Oakland (OAK) 2 12:35 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-02-01 through 2026-02-06
Mon,Sun 06:30 Oakland (OAK) 2 12:35 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 06:30 Oakland (OAK) 2 12:35 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-02-17 through 2026-02-23
Mon 06:30 Oakland (OAK) 2 12:35 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2026-03-02
Mon,Thu,Fri 06:40 Oakland (OAK) 2 12:45 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-02-12 through 2026-02-16
Sat 06:40 Oakland (OAK) 2 12:45 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-02-14 through 2026-02-28
Thu,Fri,Sun 06:40 Oakland (OAK) 2 12:45 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-02-20 through 2026-03-01
Mon-Fri 11:10 Oakland (OAK) 2 17:15 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 11:10 Oakland (OAK) 2 17:15 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-01-18 through 2026-01-23
Mon-Fri 11:10 Oakland (OAK) 2 17:15 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-01-26 through 2026-02-04
Tue,Wed 11:10 Oakland (OAK) 2 17:15 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-02-10 through 2026-02-11
Tue,Wed 11:10 Oakland (OAK) 2 17:15 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-02-18 through 2026-03-04
Sun 11:35 Oakland (OAK) 2 17:40 Chicago Midway (MDW) Southwest Airlines WN 4248 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2026-02-08
Sun 05:40 Oakland (OAK) 2 11:40 Chicago Midway (MDW) Southwest Airlines WN 4295 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-08-09 through 2026-09-27
Sat 23:55 Oakland (OAK) 2 06:55 Chicago Midway (MDW) Southwest Airlines WN 4512 Non-stop Boeing 737-800 (73H) 4:00 Operates only on 2026-03-07 The flight arrives 1 day after departure.
Non-Direct Flights:
Thu 09:20 Oakland (OAK) 2 17:05 Chicago Midway (MDW) Southwest Airlines WN 143 1-stop Boeing 737-700 (73W) 5:45 Valid until 2026-01-01
Sat 17:00 Oakland (OAK) 2 00:35 Chicago Midway (MDW) Southwest Airlines WN 1226 1-stop Boeing 737-700 (Scimitar Winglets) 5:35 Operates only on 2026-01-03 The flight arrives 1 day after departure.
Sat 05:05 Oakland (OAK) 2 14:00 Chicago Midway (MDW) Southwest Airlines WN 1692 1-stop Boeing 737 MAX 8 (7M8) 6:55 Valid until 2026-01-03
Mon,Thu,Fri 09:00 Oakland (OAK) 2 18:00 Chicago Midway (MDW) Southwest Airlines WN 3081 1-stop Boeing 737-800 (73H) 7:00 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 15:55 Oakland (OAK) 2 23:40 Chicago Midway (MDW) Southwest Airlines WN 3590 1-stop Boeing 737-800 (73H) 5:45 Effective 2026-03-05 through 2026-04-06
Mon,Thu,Fri 10:00 Oakland (OAK) 2 18:00 Chicago Midway (MDW) Southwest Airlines WN 3910 1-stop Boeing 737-700 (Scimitar Winglets) 6:00 Effective 2026-03-05 through 2026-04-06
Mon,Tue,Fri,Sun 06:35 Oakland (OAK) 2 14:35 Chicago Midway (MDW) Southwest Airlines WN 4545 1-stop Boeing 737-800 (73H) 6:00 Valid until 2026-01-04
Tue,Wed 10:15 Oakland (OAK) 2 20:00 Chicago Midway (MDW) Southwest Airlines WN 2246 2-stop Boeing 737-700 (Scimitar Winglets) 7:45 Effective 2026-06-09 through 2026-07-29
Sun 05:55 Oakland (OAK) 2 17:55 Chicago Midway (MDW) Southwest Airlines WN 1142 3-stop Boeing 737-700 (Scimitar Winglets) 10:00 Effective 2026-03-08 through 2026-04-05

A domestic route departing from the Oakland airport (OAK) and arriving at Chicago Midway 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 4:05.

Return (MDW-OAK) flights

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN174

13:30

Oakland (OAK) 2

19:30

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN199

05:10

Oakland (OAK) 2

11:15

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN814

05:25

Oakland (OAK) 2

11:30

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1150

05:40

Oakland (OAK) 2

11:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1150

05:45

Oakland (OAK) 2

11:45

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 WN1150

05:50

Oakland (OAK) 2

11:55

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2211

05:05

Oakland (OAK) 2

11:10

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2363

05:25

Oakland (OAK) 2

11:30

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 WN2363

11:00

Oakland (OAK) 2

17:05

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2744

05:10

Oakland (OAK) 2

11:15

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 WN2761

05:55

Oakland (OAK) 2

12:00

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2986

23:55

Oakland (OAK) 2

05:55(+1)

Chicago Midway (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat

Sun

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3059

23:55

Oakland (OAK) 2

06:00(+1)

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)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3551

05:50

Oakland (OAK) 2

11:55

Chicago Midway (MDW)

Effective 2026-04-07 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 WN3551

05:55

Oakland (OAK) 2

12:00

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 WN3552

23:55

Oakland (OAK) 2

06:00(+1)

Chicago Midway (MDW)

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

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 WN3808

05:25

Oakland (OAK) 2

11:30

Chicago Midway (MDW)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN3816

10:35

Oakland (OAK) 2

16:35

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4069

23:55

Oakland (OAK) 2

05:55(+1)

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN4069

23:55

Oakland (OAK) 2

05:55(+1)

Chicago Midway (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat

Sun

Duration: 4:00, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN4248

05:55

Oakland (OAK) 2

12:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN4248

06:30

Oakland (OAK) 2

12:35

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4248

06:30

Oakland (OAK) 2

12:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4248

06:30

Oakland (OAK) 2

12:35

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4248

06:30

Oakland (OAK) 2

12:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4248

06:30

Oakland (OAK) 2

12:35

Chicago Midway (MDW)

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

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4248

06:30

Oakland (OAK) 2

12:35

Chicago Midway (MDW)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4248

06:40

Oakland (OAK) 2

12:45

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4248

06:40

Oakland (OAK) 2

12:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN4248

06:40

Oakland (OAK) 2

12:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4248

11:10

Oakland (OAK) 2

17:15

Chicago Midway (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4248

11:10

Oakland (OAK) 2

17:15

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4248

11:10

Oakland (OAK) 2

17:15

Chicago Midway (MDW)

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4248

11:10

Oakland (OAK) 2

17:15

Chicago Midway (MDW)

Effective 2026-02-10 through 2026-02-11

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4248

11:10

Oakland (OAK) 2

17:15

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4248

11:35

Oakland (OAK) 2

17:40

Chicago Midway (MDW)

Operates only on 2026-02-08

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4295

05:40

Oakland (OAK) 2

11:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4512

23:55

Oakland (OAK) 2

06:55(+1)

Chicago Midway (MDW)

Operates only on 2026-03-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Non-Direct Flights:

Southwest Airlines WN143

09:20

Oakland (OAK) 2

17:05

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 5:45, 1-stop
Boeing 737-700 (73W)

Non-Direct Flights:

Southwest Airlines WN1226

17:00

Oakland (OAK) 2

00:35(+1)

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:35, 1-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.

Non-Direct Flights:

Southwest Airlines WN1692

05:05

Oakland (OAK) 2

14:00

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:55, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN3081

09:00

Oakland (OAK) 2

18:00

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 7:00, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN3590

15:55

Oakland (OAK) 2

23:40

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 5:45, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN3910

10:00

Oakland (OAK) 2

18:00

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4545

06:35

Oakland (OAK) 2

14:35

Chicago Midway (MDW)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 6:00, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN2246

10:15

Oakland (OAK) 2

20:00

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 7:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1142

05:55

Oakland (OAK) 2

17:55

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 10:00, 3-stop
Boeing 737-700 (Scimitar Winglets)

A domestic route departing from the Oakland airport (OAK) and arriving at Chicago Midway 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 4:05.

Return (MDW-OAK) flights

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