Southwest Airlines flights from Oakland (OAK) to Midway, Chicago (MDW).

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sat 06:20 Oakland (OAK) 2 12:30 Midway, Chicago (MDW)
Southwest Airlines WN 2947 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2024-12-07 through 2024-12-14
Sun 11:00 Oakland (OAK) 2 17:10 Midway, Chicago (MDW)
Southwest Airlines WN 3577 Non-stop Boeing 737-800 (73H) 4:10 Operates only on 2024-09-01
Tue,Wed 10:50 Oakland (OAK) 2 16:55 Midway, Chicago (MDW)
Southwest Airlines WN 3689 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-10-08 through 2024-10-30
Sun 17:45 Oakland (OAK) 2 23:50 Midway, Chicago (MDW)
Southwest Airlines WN 3689 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2024-10-06 through 2024-10-27
Mon,Thu,Fri 13:05 Oakland (OAK) 2 19:10 Midway, Chicago (MDW)
Southwest Airlines WN 3746 Non-stop Boeing 737-800 (73H) 4:05 Effective 2024-10-03 through 2024-10-28
Fri 13:05 Oakland (OAK) 2 19:10 Midway, Chicago (MDW)
Southwest Airlines WN 3746 Non-stop Boeing 737-800 (73H) 4:05 Operates only on 2024-11-01
Mon,Thu,Fri 05:55 Oakland (OAK) 2 12:10 Midway, Chicago (MDW)
Southwest Airlines WN 3788 Non-stop Boeing 737-800 (73H) 4:15 Valid until 2024-09-30
Thu 10:30 Oakland (OAK) 2 16:40 Midway, Chicago (MDW)
Southwest Airlines WN 3867 Non-stop Boeing 737-800 (73H) 4:10 Operates only on 2024-10-31
Sat 11:50 Oakland (OAK) 2 17:55 Midway, Chicago (MDW)
Southwest Airlines WN 4122 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-02-15 through 2025-03-01
Sat 06:10 Oakland (OAK) 2 12:15 Midway, Chicago (MDW)
Southwest Airlines WN 4189 Non-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-02-15 through 2025-03-01
Non-Direct Flights:
Sat 09:55 Oakland (OAK) 2 17:45 Midway, Chicago (MDW)
Southwest Airlines WN 207 1-stop Boeing 737-700 (73W) 5:50 Effective 2024-11-23 through 2024-11-30
Sat 09:55 Oakland (OAK) 2 17:45 Midway, Chicago (MDW)
Southwest Airlines WN 207 1-stop Boeing 737-700 (73W) 5:50 Effective 2024-12-21 through 2025-01-04
Sat 05:25 Oakland (OAK) 2 13:45 Midway, Chicago (MDW)
Southwest Airlines WN 423 1-stop Boeing 737-700 (73W) 6:20 Effective 2024-11-23 through 2024-11-30
Sat 05:25 Oakland (OAK) 2 13:45 Midway, Chicago (MDW)
Southwest Airlines WN 423 1-stop Boeing 737-700 (73W) 6:20 Effective 2024-12-21 through 2025-01-04
Tue,Wed 12:40 Oakland (OAK) 2 21:10 Midway, Chicago (MDW)
Southwest Airlines WN 554 1-stop Boeing 737-700 (73W) 6:30 Valid until 2024-10-02
Sat 07:15 Oakland (OAK) 2 16:15 Midway, Chicago (MDW)
Southwest Airlines WN 667 1-stop Boeing 737-800 (73H) 7:00 Effective 2025-01-11 through 2025-02-08
Mon,Wed 15:30 Oakland (OAK) 2 23:20 Midway, Chicago (MDW)
Southwest Airlines WN 815 1-stop Boeing 737-700 (73W) 5:50 Effective 2024-11-04 through 2024-11-06
Tue,Wed 15:30 Oakland (OAK) 2 23:20 Midway, Chicago (MDW)
Southwest Airlines WN 815 1-stop Boeing 737-700 (73W) 5:50 Effective 2024-11-12 through 2024-11-20
Tue-Fri 15:30 Oakland (OAK) 2 23:20 Midway, Chicago (MDW)
Southwest Airlines WN 815 1-stop Boeing 737-700 (73W) 5:50 Effective 2024-11-29 through 2024-12-06
Mon-Thu 15:30 Oakland (OAK) 2 23:20 Midway, Chicago (MDW)
Southwest Airlines WN 815 1-stop Boeing 737-700 (73W) 5:50 Effective 2024-12-09 through 2024-12-18
Tue,Wed 15:30 Oakland (OAK) 2 23:20 Midway, Chicago (MDW)
Southwest Airlines WN 815 1-stop Boeing 737-700 (73W) 5:50 Effective 2024-12-24 through 2025-01-01
Mon 15:30 Oakland (OAK) 2 23:20 Midway, Chicago (MDW)
Southwest Airlines WN 815 1-stop Boeing 737-700 (73W) 5:50 Operates only on 2025-01-06
Sat 07:00 Oakland (OAK) 2 14:20 Midway, Chicago (MDW)
Southwest Airlines WN 1119 1-stop Boeing 737-700 (73W) 5:20 Effective 2025-02-15 through 2025-03-01
Mon,Thu,Fri 06:00 Oakland (OAK) 2 13:50 Midway, Chicago (MDW)
Southwest Airlines WN 1123 1-stop Boeing 737-700 (73W) 5:50 Effective 2024-10-03 through 2024-10-28
Fri 06:00 Oakland (OAK) 2 13:50 Midway, Chicago (MDW)
Southwest Airlines WN 1123 1-stop Boeing 737-700 (73W) 5:50 Operates only on 2024-11-01
Mon,Thu,Fri 15:55 Oakland (OAK) 2 23:20 Midway, Chicago (MDW)
Southwest Airlines WN 1575 1-stop Boeing 737-700 (73W) 5:25 Valid until 2024-09-30
Sun 15:55 Oakland (OAK) 2 23:45 Midway, Chicago (MDW)
Southwest Airlines WN 1880 1-stop Boeing 737-700 (73W) 5:50 Effective 2024-09-08 through 2024-09-29
Sun 06:10 Oakland (OAK) 2 14:00 Midway, Chicago (MDW)
Southwest Airlines WN 2014 1-stop Boeing 737-700 (73W) 5:50 Operates only on 2024-12-01
Thu,Fri,Sun 16:50 Oakland (OAK) 2 00:50 Midway, Chicago (MDW)
Southwest Airlines WN 2316 1-stop Boeing 737-700 (73W) 6:00 Effective 2024-11-03 through 2024-11-10
The flight arrives 1 day after departure.
Mon,Thu,Fri,Sun 16:50 Oakland (OAK) 2 00:50 Midway, Chicago (MDW)
Southwest Airlines WN 2316 1-stop Boeing 737-700 (73W) 6:00 Effective 2024-11-11 through 2024-11-25
The flight arrives 1 day after departure.
Fri,Sun 16:50 Oakland (OAK) 2 00:50 Midway, Chicago (MDW)
Southwest Airlines WN 2316 1-stop Boeing 737-700 (73W) 6:00 Effective 2024-12-08 through 2024-12-15
The flight arrives 1 day after departure.
Thu 16:50 Oakland (OAK) 2 00:50 Midway, Chicago (MDW)
Southwest Airlines WN 2316 1-stop Boeing 737-700 (73W) 6:00 Operates only on 2024-12-19
The flight arrives 1 day after departure.
Fri 16:50 Oakland (OAK) 2 00:50 Midway, Chicago (MDW)
Southwest Airlines WN 2316 1-stop Boeing 737-700 (73W) 6:00 Operates only on 2025-01-03
The flight arrives 1 day after departure.
Sun 10:45 Oakland (OAK) 2 19:40 Midway, Chicago (MDW)
Southwest Airlines WN 2393 1-stop Boeing 737-800 (73H) 6:55 Effective 2024-09-08 through 2024-09-29
Tue,Wed 12:50 Oakland (OAK) 2 20:55 Midway, Chicago (MDW)
Southwest Airlines WN 2426 1-stop Boeing 737-700 (73W) 6:05 Valid until 2024-10-02
Sat 06:35 Oakland (OAK) 2 15:35 Midway, Chicago (MDW)
Southwest Airlines WN 2456 1-stop Boeing 737 MAX 8 (7M8) 7:00 Effective 2024-10-05 through 2024-11-02
Tue,Wed 08:05 Oakland (OAK) 2 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 2456 1-stop Boeing 737-800 (73H) 6:55 Effective 2024-10-08 through 2024-10-30
Sun 08:55 Oakland (OAK) 2 16:50 Midway, Chicago (MDW)
Southwest Airlines WN 2574 1-stop Boeing 737-700 (73W) 5:55 Effective 2024-10-06 through 2024-10-27
Sun 05:15 Oakland (OAK) 2 14:10 Midway, Chicago (MDW)
Southwest Airlines WN 2765 1-stop Boeing 737-800 (73H) 6:55 Operates only on 2024-12-01
Sat 09:05 Oakland (OAK) 2 17:20 Midway, Chicago (MDW)
Southwest Airlines WN 3199 1-stop Boeing 737-700 (73W) 6:15 Effective 2024-11-09 through 2024-11-16
Sat 09:05 Oakland (OAK) 2 17:20 Midway, Chicago (MDW)
Southwest Airlines WN 3199 1-stop Boeing 737-700 (73W) 6:15 Effective 2024-12-07 through 2024-12-14
Sat 13:20 Oakland (OAK) 2 21:25 Midway, Chicago (MDW)
Southwest Airlines WN 3883 1-stop Boeing 737-700 (73W) 6:05 Effective 2024-10-05 through 2024-11-02
Mon,Thu,Fri,Sun 06:05 Oakland (OAK) 2 15:05 Midway, Chicago (MDW)
Southwest Airlines WN 3929 1-stop Boeing 737 MAX 8 (7M8) 7:00 Effective 2025-02-13 through 2025-02-17
Thu,Fri,Sun 06:05 Oakland (OAK) 2 15:05 Midway, Chicago (MDW)
Southwest Airlines WN 3929 1-stop Boeing 737 MAX 8 (7M8) 7:00 Effective 2025-02-21 through 2025-03-02
Sun 09:45 Oakland (OAK) 2 18:05 Midway, Chicago (MDW)
Southwest Airlines WN 4410 1-stop Boeing 737-800 (73H) 6:20 Effective 2024-09-08 through 2024-09-29
Thu 05:35 Oakland (OAK) 2 14:30 Midway, Chicago (MDW)
Southwest Airlines WN 427 2-stop Boeing 737-700 (73W) 6:55 Operates only on 2024-10-31
Mon,Thu,Fri 07:45 Oakland (OAK) 2 17:10 Midway, Chicago (MDW)
Southwest Airlines WN 582 2-stop Boeing 737-700 (73W) 7:25 Effective 2024-10-03 through 2024-10-28
Fri 07:45 Oakland (OAK) 2 17:10 Midway, Chicago (MDW)
Southwest Airlines WN 582 2-stop Boeing 737-700 (73W) 7:25 Operates only on 2024-11-01
Sat 08:45 Oakland (OAK) 2 19:00 Midway, Chicago (MDW)
Southwest Airlines WN 948 2-stop Boeing 737-700 (73W) 8:15 Valid until 2024-09-28
Sun 05:30 Oakland (OAK) 2 15:50 Midway, Chicago (MDW)
Southwest Airlines WN 4325 2-stop Boeing 737-700 (73W) 8:20 Operates only on 2024-12-01
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Southwest Airlines flights from Oakland (OAK) to Midway, Chicago (MDW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2024-12-07 through 2024-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-09-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:10, non-stop
Boeing 737-800 (73H)

Effective 2024-10-08 through 2024-10-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-10-06 through 2024-10-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 4:05, non-stop
Boeing 737-800 (73H)

Valid until 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:15, non-stop
Boeing 737-800 (73H)

Operates only on 2024-10-31
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:10, non-stop
Boeing 737-800 (73H)

Effective 2025-02-15 through 2025-03-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-02-15 through 2025-03-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:05, non-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Effective 2024-11-23 through 2024-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-21 through 2025-01-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-23 through 2024-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:20, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-21 through 2025-01-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:20, 1-stop
Boeing 737-700 (73W)

Valid until 2024-10-02
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 6:30, 1-stop
Boeing 737-700 (73W)

Effective 2025-01-11 through 2025-02-08
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 7:00, 1-stop
Boeing 737-800 (73H)

Effective 2024-11-04 through 2024-11-06
Mon
Tue
-
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-12 through 2024-11-20
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-29 through 2024-12-06
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-09 through 2024-12-18
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-24 through 2025-01-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-01-06
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Effective 2025-02-15 through 2025-03-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:20, 1-stop
Boeing 737-700 (73W)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Valid until 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:25, 1-stop
Boeing 737-700 (73W)

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:50, 1-stop
Boeing 737-700 (73W)

Effective 2024-11-03 through 2024-11-10
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 6:00, 1-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Effective 2024-11-11 through 2024-11-25
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 6:00, 1-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Effective 2024-12-08 through 2024-12-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 6:00, 1-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Operates only on 2024-12-19
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 6:00, 1-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Operates only on 2025-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 6:00, 1-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:55, 1-stop
Boeing 737-800 (73H)

Valid until 2024-10-02
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 6:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-10-05 through 2024-11-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 7:00, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-10-08 through 2024-10-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 6:55, 1-stop
Boeing 737-800 (73H)

Effective 2024-10-06 through 2024-10-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:55, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:55, 1-stop
Boeing 737-800 (73H)

Effective 2024-11-09 through 2024-11-16
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:15, 1-stop
Boeing 737-700 (73W)

Effective 2024-12-07 through 2024-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:15, 1-stop
Boeing 737-700 (73W)

Effective 2024-10-05 through 2024-11-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:05, 1-stop
Boeing 737-700 (73W)

Effective 2025-02-13 through 2025-02-17
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 7:00, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-02-21 through 2025-03-02
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 7:00, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:20, 1-stop
Boeing 737-800 (73H)

Operates only on 2024-10-31
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 6:55, 2-stop
Boeing 737-700 (73W)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 7:25, 2-stop
Boeing 737-700 (73W)

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 7:25, 2-stop
Boeing 737-700 (73W)

Valid until 2024-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 8:15, 2-stop
Boeing 737-700 (73W)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 8:20, 2-stop
Boeing 737-700 (73W)
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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 4:15.