All airlines flying from Midland (MAF) to Chicago Midway (MDW).

Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Mon 14:15 Midland (MAF) 18:25 Chicago Midway (MDW)
Southwest Airlines WN 3275 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Operates only on 2026-01-05
Thu,Fri,Sun 10:45 Midland (MAF) 17:05 Chicago Midway (MDW)
Southwest Airlines WN 4990 2-stop Boeing 737-700 (Scimitar Winglets) 6:20 Effective 2026-01-11 through 2026-01-16
Mon,Sun 10:45 Midland (MAF) 17:05 Chicago Midway (MDW)
Southwest Airlines WN 4990 2-stop Boeing 737-700 (Scimitar Winglets) 6:20 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 10:45 Midland (MAF) 17:05 Chicago Midway (MDW)
Southwest Airlines WN 4990 2-stop Boeing 737-700 (Scimitar Winglets) 6:20 Effective 2026-02-01 through 2026-02-06
Mon,Sun 10:45 Midland (MAF) 17:05 Chicago Midway (MDW)
Southwest Airlines WN 4990 2-stop Boeing 737-700 (Scimitar Winglets) 6:20 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 10:45 Midland (MAF) 17:05 Chicago Midway (MDW)
Southwest Airlines WN 4990 2-stop Boeing 737-700 (Scimitar Winglets) 6:20 Effective 2026-02-17 through 2026-02-23
Mon 10:45 Midland (MAF) 17:05 Chicago Midway (MDW)
Southwest Airlines WN 4990 2-stop Boeing 737-700 (Scimitar Winglets) 6:20 Operates only on 2026-03-02




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All airlines flying from Midland (MAF) to Chicago Midway (MDW).
Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Southwest Airlines WN3275
14:15
Midland (MAF)

18:25
Chicago Midway (MDW)
Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4990
10:45
Midland (MAF)

17:05
Chicago Midway (MDW)
Effective 2026-01-11 through 2026-01-16
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 6:20, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4990
10:45
Midland (MAF)

17:05
Chicago Midway (MDW)
Effective 2026-01-19 through 2026-01-25
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:20, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4990
10:45
Midland (MAF)

17:05
Chicago Midway (MDW)
Effective 2026-02-01 through 2026-02-06
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 6:20, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4990
10:45
Midland (MAF)

17:05
Chicago Midway (MDW)
Effective 2026-02-09 through 2026-02-15
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:20, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4990
10:45
Midland (MAF)

17:05
Chicago Midway (MDW)
Effective 2026-02-17 through 2026-02-23
Mon
Tue
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 6:20, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4990
10:45
Midland (MAF)

17:05
Chicago Midway (MDW)
Operates only on 2026-03-02
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 6:20, 2-stop
Boeing 737-700 (Scimitar Winglets)
  • A domestic route departing from the Midland airport (MAF) and arriving at Chicago Midway airport (MDW).
  • The flight distance is 1046 miles, or 1683 km.
  • The timezone of both the departure and the arrival airports is UTC-6 . Current time at both airports is (loading...).
Return (MDW-MAF) flights
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