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

Ad box here 7322741189 I FlightInfo Top Box

FLIGHT SCHEDULE
Non-Direct Flights:
Mon-Fri 09:20 Oakland (OAK) 2 17:05 Midway, Chicago (MDW) Southwest Airlines WN 143 1-stop Boeing 737-700 (Scimitar Winglets) 5:45 Effective 2025-12-02 through 2025-12-11
Mon-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 2025-12-15 through 2025-12-17
Wed,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 2025-12-24 through 2026-01-01
Fri 10:10 Oakland (OAK) 2 17:45 Midway, Chicago (MDW) Southwest Airlines WN 206 1-stop Boeing 737-700 (73W) 5:35 Operates only on 2025-07-04
Mon,Thu,Fri 10:30 Oakland (OAK) 2 19:20 Midway, Chicago (MDW) Southwest Airlines WN 222 1-stop Boeing 737 MAX 8 (7M8) 6:50 Effective 2025-08-07 through 2025-09-29
Tue,Wed 09:55 Oakland (OAK) 2 17:45 Midway, Chicago (MDW) Southwest Airlines WN 654 1-stop Boeing 737-700 (73W) 5:50 Effective 2025-08-05 through 2025-10-01
Tue,Wed 16:10 Oakland (OAK) 2 00:25 Midway, Chicago (MDW) Southwest Airlines WN 925 1-stop Boeing 737 MAX 8 (7M8) 6:15 Effective 2025-10-07 through 2025-10-29 The flight arrives 1 day after departure.
Sat 17:00 Oakland (OAK) 2 00:35 Midway, Chicago (MDW) Southwest Airlines WN 1226 1-stop Boeing 737-700 (Scimitar Winglets) 5:35 Effective 2025-11-22 through 2025-11-29 The flight arrives 1 day after departure.
Sat 17:00 Oakland (OAK) 2 00:35 Midway, Chicago (MDW) Southwest Airlines WN 1226 1-stop Boeing 737-700 (Scimitar Winglets) 5:35 Effective 2025-12-20 through 2026-01-03 The flight arrives 1 day after departure.
Mon,Thu,Fri 06:40 Oakland (OAK) 2 15:45 Midway, Chicago (MDW) Southwest Airlines WN 1252 1-stop Boeing 737-800 (73H) 7:05 Valid until 2025-06-02
Mon,Thu,Fri 06:15 Oakland (OAK) 2 14:15 Midway, Chicago (MDW) Southwest Airlines WN 1546 1-stop Boeing 737-700 (73W) 6:00 Effective 2025-08-07 through 2025-09-29
Fri 11:50 Oakland (OAK) 2 20:00 Midway, Chicago (MDW) Southwest Airlines WN 1664 1-stop Boeing 737-700 (73W) 6:10 Operates only on 2025-07-04
Sat 05:00 Oakland (OAK) 2 13:55 Midway, Chicago (MDW) Southwest Airlines WN 1692 1-stop Boeing 737 MAX 8 (7M8) 6:55 Effective 2025-11-22 through 2025-11-29
Sat 05:00 Oakland (OAK) 2 13:55 Midway, Chicago (MDW) Southwest Airlines WN 1692 1-stop Boeing 737 MAX 8 (7M8) 6:55 Effective 2025-12-20 through 2026-01-03
Tue,Wed 08:50 Oakland (OAK) 2 17:10 Midway, Chicago (MDW) Southwest Airlines WN 1981 1-stop Boeing 737 MAX 8 (7M8) 6:20 Effective 2025-10-07 through 2025-10-29
Sun 09:10 Oakland (OAK) 2 18:25 Midway, Chicago (MDW) Southwest Airlines WN 1987 1-stop Boeing 737 MAX 8 (7M8) 7:15 Operates only on 2025-05-25
Sun 11:10 Oakland (OAK) 2 19:25 Midway, Chicago (MDW) Southwest Airlines WN 2139 1-stop Boeing 737 MAX 8 (7M8) 6:15 Effective 2025-10-05 through 2025-10-26
Tue,Wed 12:10 Oakland (OAK) 2 20:10 Midway, Chicago (MDW) Southwest Airlines WN 2189 1-stop Boeing 737-700 (73W) 6:00 Effective 2025-06-10 through 2025-07-30
Tue,Wed 09:10 Oakland (OAK) 2 17:20 Midway, Chicago (MDW) Southwest Airlines WN 2932 1-stop Boeing 737-700 (73W) 6:10 Valid until 2025-06-04
Sun 05:50 Oakland (OAK) 2 14:10 Midway, Chicago (MDW) Southwest Airlines WN 2963 1-stop Boeing 737 MAX 8 (7M8) 6:20 Effective 2025-06-08 through 2025-08-03
Sun 08:55 Oakland (OAK) 2 16:50 Midway, Chicago (MDW) Southwest Airlines WN 3178 1-stop Boeing 737 MAX 8 (7M8) 5:55 Operates only on 2025-11-30
Mon,Thu,Fri 05:55 Oakland (OAK) 2 14:10 Midway, Chicago (MDW) Southwest Airlines WN 3780 1-stop Boeing 737-700 (73W) 6:15 Effective 2025-08-07 through 2025-09-29
Tue,Wed 06:15 Oakland (OAK) 2 15:10 Midway, Chicago (MDW) Southwest Airlines WN 4027 1-stop Boeing 737-800 (73H) 6:55 Effective 2025-10-07 through 2025-10-29
Sat 12:20 Oakland (OAK) 2 20:25 Midway, Chicago (MDW) Southwest Airlines WN 4170 1-stop Boeing 737-700 (73W) 6:05 Effective 2025-06-07 through 2025-08-02
Mon-Wed 06:40 Oakland (OAK) 2 14:35 Midway, Chicago (MDW) Southwest Airlines WN 4545 1-stop Boeing 737-800 (73H) 5:55 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 06:40 Oakland (OAK) 2 14:35 Midway, Chicago (MDW) Southwest Airlines WN 4545 1-stop Boeing 737-800 (73H) 5:55 Effective 2025-12-19 through 2026-01-04
Sun 08:05 Oakland (OAK) 2 17:45 Midway, Chicago (MDW) Southwest Airlines WN 1365 2-stop Boeing 737-700 (73W) 7:40 Valid until 2025-05-18
Sun 08:05 Oakland (OAK) 2 17:45 Midway, Chicago (MDW) Southwest Airlines WN 1365 2-stop Boeing 737-700 (73W) 7:40 Operates only on 2025-06-01
Mon,Thu,Fri 08:55 Oakland (OAK) 2 18:05 Midway, Chicago (MDW) Southwest Airlines WN 1537 2-stop Boeing 737-700 (Scimitar Winglets) 7:10 Effective 2025-10-02 through 2025-10-31
Sat 10:00 Oakland (OAK) 2 18:50 Midway, Chicago (MDW) Southwest Airlines WN 2891 2-stop Boeing 737-700 (73W) 6:50 Valid until 2025-05-31
Sun 10:25 Oakland (OAK) 2 19:40 Midway, Chicago (MDW) Southwest Airlines WN 3855 2-stop Boeing 737-700 (73W) 7:15 Effective 2025-08-10 through 2025-08-24
Sun 10:25 Oakland (OAK) 2 19:40 Midway, Chicago (MDW) Southwest Airlines WN 3855 2-stop Boeing 737-700 (73W) 7:15 Effective 2025-09-07 through 2025-09-28
Sun 07:25 Oakland (OAK) 2 19:35 Midway, Chicago (MDW) Southwest Airlines WN 1786 3-stop Boeing 737-700 (73W) 10:10 Effective 2025-08-10 through 2025-08-24
Sun 07:25 Oakland (OAK) 2 19:35 Midway, Chicago (MDW) Southwest Airlines WN 1786 3-stop Boeing 737-700 (73W) 10:10 Effective 2025-09-07 through 2025-09-28
Sun 08:15 Oakland (OAK) 2 19:40 Midway, Chicago (MDW) Southwest Airlines WN 2425 3-stop Boeing 737-700 (Scimitar Winglets) 9:25 Operates only on 2025-11-30
Sun 06:15 Oakland (OAK) 2 21:15 Midway, Chicago (MDW) Southwest Airlines WN 1895 4-stop Boeing 737-700 (73W) 13:00 Effective 2025-06-08 through 2025-08-03

Ad flat here 8924483383 I FlightInfo Lower

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

Feedback - Disclaimer - Privacy - new_base.html - DESKTOP - CACHE: False - LANG: en - IS_EU: False

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

Ad mobi flat here (320x100px) 9629219771 M FlightInfo Top Flat

FLIGHT SCHEDULE

Non-Direct Flights:

Southwest Airlines WN143

09:20

Oakland (OAK) 2

17:05

Midway, Chicago (MDW)

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

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 2025-12-15 through 2025-12-17

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 2025-12-24 through 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN206

10:10

Oakland (OAK) 2

17:45

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 5:35, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN222

10:30

Oakland (OAK) 2

19:20

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:50, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN654

09:55

Oakland (OAK) 2

17:45

Midway, Chicago (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN925

16:10

Oakland (OAK) 2

00:25(+1)

Midway, Chicago (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:15, 1-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN1226

17:00

Oakland (OAK) 2

00:35(+1)

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN1226

17:00

Oakland (OAK) 2

00:35(+1)

Midway, Chicago (MDW)

Effective 2025-12-20 through 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.

Southwest Airlines WN1252

06:40

Oakland (OAK) 2

15:45

Midway, Chicago (MDW)

Valid until 2025-06-02

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 7:05, 1-stop
Boeing 737-800 (73H)

Southwest Airlines WN1546

06:15

Oakland (OAK) 2

14:15

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:00, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN1664

11:50

Oakland (OAK) 2

20:00

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 6:10, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN1692

05:00

Oakland (OAK) 2

13:55

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN1692

05:00

Oakland (OAK) 2

13:55

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN1981

08:50

Oakland (OAK) 2

17:10

Midway, Chicago (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:20, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1987

09:10

Oakland (OAK) 2

18:25

Midway, Chicago (MDW)

Operates only on 2025-05-25

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2139

11:10

Oakland (OAK) 2

19:25

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2189

12:10

Oakland (OAK) 2

20:10

Midway, Chicago (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:00, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN2932

09:10

Oakland (OAK) 2

17:20

Midway, Chicago (MDW)

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:10, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN2963

05:50

Oakland (OAK) 2

14:10

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:20, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3178

08:55

Oakland (OAK) 2

16:50

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:55, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3780

05:55

Oakland (OAK) 2

14:10

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 6:15, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN4027

06:15

Oakland (OAK) 2

15:10

Midway, Chicago (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:55, 1-stop
Boeing 737-800 (73H)

Southwest Airlines WN4170

12:20

Oakland (OAK) 2

20:25

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:05, 1-stop
Boeing 737-700 (73W)

Southwest Airlines WN4545

06:40

Oakland (OAK) 2

14:35

Midway, Chicago (MDW)

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:55, 1-stop
Boeing 737-800 (73H)

Southwest Airlines WN4545

06:40

Oakland (OAK) 2

14:35

Midway, Chicago (MDW)

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

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 5:55, 1-stop
Boeing 737-800 (73H)

Southwest Airlines WN1365

08:05

Oakland (OAK) 2

17:45

Midway, Chicago (MDW)

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:40, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN1365

08:05

Oakland (OAK) 2

17:45

Midway, Chicago (MDW)

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:40, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN1537

08:55

Oakland (OAK) 2

18:05

Midway, Chicago (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 7:10, 2-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2891

10:00

Oakland (OAK) 2

18:50

Midway, Chicago (MDW)

Valid until 2025-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:50, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN3855

10:25

Oakland (OAK) 2

19:40

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:15, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN3855

10:25

Oakland (OAK) 2

19:40

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:15, 2-stop
Boeing 737-700 (73W)

Southwest Airlines WN1786

07:25

Oakland (OAK) 2

19:35

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 10:10, 3-stop
Boeing 737-700 (73W)

Southwest Airlines WN1786

07:25

Oakland (OAK) 2

19:35

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 10:10, 3-stop
Boeing 737-700 (73W)

Southwest Airlines WN2425

08:15

Oakland (OAK) 2

19:40

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 9:25, 3-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN1895

06:15

Oakland (OAK) 2

21:15

Midway, Chicago (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 13:00, 4-stop
Boeing 737-700 (73W)

Ad mobi box here (300x250px) 6815354179 M FlightInfo Bottom Box

Parallax here OAK-MDW

prev Page 2 / 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

Feedback - Disclaimer - Privacy - new_base.html - MOBILE

- CACHE: False - LANG: en - IS_EU: False