All airlines flying from Chicago Midway (MDW) to San Jose del Cabo (SJD).

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sat 08:10 Chicago Midway (MDW) 12:00 San Jose del Cabo (SJD) 2
Southwest Airlines WN 3636 Non-stop Boeing 737-700 (Scimitar Winglets) 4:50 Operates only on 2026-01-03
Thu,Fri 08:40 Chicago Midway (MDW) 12:40 San Jose del Cabo (SJD) 2
Southwest Airlines WN 3636 Non-stop Boeing 737-700 (Scimitar Winglets) 5:00 Effective 2026-03-05 through 2026-03-06
Mon,Thu,Fri 08:40 Chicago Midway (MDW) 11:40 San Jose del Cabo (SJD) 2
Southwest Airlines WN 3636 Non-stop Boeing 737-700 (Scimitar Winglets) 5:00 Effective 2026-03-09 through 2026-04-06
Sat 08:55 Chicago Midway (MDW) 12:50 San Jose del Cabo (SJD) 2
Southwest Airlines WN 3636 Non-stop Boeing 737-700 (Scimitar Winglets) 4:55 Operates only on 2026-03-07
Sat 08:55 Chicago Midway (MDW) 11:50 San Jose del Cabo (SJD) 2
Southwest Airlines WN 3636 Non-stop Boeing 737-700 (Scimitar Winglets) 4:55 Effective 2026-03-14 through 2026-04-04
Sun 09:30 Chicago Midway (MDW) 12:25 San Jose del Cabo (SJD) 2
Southwest Airlines WN 3636 Non-stop Boeing 737-700 (Scimitar Winglets) 4:55 Effective 2026-03-08 through 2026-04-05
Tue,Wed 10:40 Chicago Midway (MDW) 13:35 San Jose del Cabo (SJD) 2
Southwest Airlines WN 3636 Non-stop Boeing 737-700 (Scimitar Winglets) 4:55 Effective 2026-03-10 through 2026-04-01




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All airlines flying from Chicago Midway (MDW) to San Jose del Cabo (SJD).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Southwest Airlines WN3636
08:10
Chicago Midway (MDW)

12:00
San Jose del Cabo (SJD) 2
Operates only on 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:50, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN3636
08:40
Chicago Midway (MDW)

12:40
San Jose del Cabo (SJD) 2
Effective 2026-03-05 through 2026-03-06
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:00, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN3636
08:40
Chicago Midway (MDW)

11:40
San Jose del Cabo (SJD) 2
Effective 2026-03-09 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:00, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN3636
08:55
Chicago Midway (MDW)

12:50
San Jose del Cabo (SJD) 2
Operates only on 2026-03-07
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:55, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN3636
08:55
Chicago Midway (MDW)

11:50
San Jose del Cabo (SJD) 2
Effective 2026-03-14 through 2026-04-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:55, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN3636
09:30
Chicago Midway (MDW)

12:25
San Jose del Cabo (SJD) 2
Effective 2026-03-08 through 2026-04-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:55, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN3636
10:40
Chicago Midway (MDW)

13:35
San Jose del Cabo (SJD) 2
Effective 2026-03-10 through 2026-04-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:55, non-stop
Boeing 737-700 (Scimitar Winglets)
  • An international route departing from Chicago Midway airport, United States (MDW) and arriving at San Jose del Cabo airport, Mexico (SJD).
  • The flight distance is 1804 miles, or 2904 km.
  • The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-7 . 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 4:50 and 5:00.
Return (SJD-MDW) flights
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