Southwest Airlines flights from Miami (MIA) to Chicago Midway (MDW).

Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Tue,Wed 13:15 Miami (MIA) 17:05 Chicago Midway (MDW)
Southwest Airlines WN 373 1-stop Boeing 737-700 (Scimitar Winglets) 4:50 Effective 2026-03-10 through 2026-04-01
Sun 13:30 Miami (MIA) 17:00 Chicago Midway (MDW)
Southwest Airlines WN 659 1-stop Boeing 737-700 (Scimitar Winglets) 4:30 Operates only on 2026-05-24
Sat 12:20 Miami (MIA) 16:55 Chicago Midway (MDW)
Southwest Airlines WN 2793 1-stop Boeing 737-700 (Scimitar Winglets) 5:35 Operates only on 2026-02-07
Tue,Wed 11:45 Miami (MIA) 15:55 Chicago Midway (MDW)
Southwest Airlines WN 3850 1-stop Boeing 737-700 (Scimitar Winglets) 5:10 Effective 2026-06-09 through 2026-07-29
Sun 14:40 Miami (MIA) 20:35 Chicago Midway (MDW)
Southwest Airlines WN 2693 2-stop Boeing 737-700 (Scimitar Winglets) 6:55 Effective 2026-06-07 through 2026-08-02
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Southwest Airlines flights from Miami (MIA) to Chicago Midway (MDW).
Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:

Effective 2026-03-10 through 2026-04-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:50, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Operates only on 2026-05-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Operates only on 2026-02-07
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:35, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:55, 2-stop
Boeing 737-700 (Scimitar Winglets)
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  • A domestic route departing from the Miami airport (MIA) and arriving at Chicago Midway airport (MDW).
  • The flight distance is 1183 miles, or 1904 km.
  • The timezone of the departure airport is UTC-5 , 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 3:05 and 3:30.