Southwest Airlines flights from Destin/Fort Walton Beach (VPS) to Chicago Midway (MDW).

Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Tue,Wed 13:35 Destin/Fort Walton Beach (VPS) 17:05 Chicago Midway (MDW)
Southwest Airlines WN 556 1-stop Boeing 737-700 (Scimitar Winglets) 3:30 Effective 2026-06-09 through 2026-07-29
Sun 10:40 Destin/Fort Walton Beach (VPS) 15:35 Chicago Midway (MDW)
Southwest Airlines WN 1092 1-stop Boeing 737-700 (Scimitar Winglets) 4:55 Operates only on 2026-05-24
Tue,Wed 07:15 Destin/Fort Walton Beach (VPS) 11:00 Chicago Midway (MDW)
Southwest Airlines WN 1473 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-06-09 through 2026-07-29
Sun 10:55 Destin/Fort Walton Beach (VPS) 14:30 Chicago Midway (MDW)
Southwest Airlines WN 2832 1-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 14:00 Destin/Fort Walton Beach (VPS) 20:10 Chicago Midway (MDW)
Southwest Airlines WN 2211 2-stop Boeing 737-700 (Scimitar Winglets) 6:10 Effective 2026-03-05 through 2026-04-06
Sun 14:00 Destin/Fort Walton Beach (VPS) 20:45 Chicago Midway (MDW)
Southwest Airlines WN 2211 2-stop Boeing 737-700 (Scimitar Winglets) 6:45 Effective 2026-03-08 through 2026-04-05




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Southwest Airlines flights from Destin/Fort Walton Beach (VPS) to Chicago Midway (MDW).
Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Southwest Airlines WN556
13:35
Destin/Fort Walton Beach (VPS)

17:05
Chicago Midway (MDW)
Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:30, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN1092
10:40
Destin/Fort Walton Beach (VPS)

15:35
Chicago Midway (MDW)
Operates only on 2026-05-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:55, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN1473
07:15
Destin/Fort Walton Beach (VPS)

11:00
Chicago Midway (MDW)
Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN2832
10:55
Destin/Fort Walton Beach (VPS)

14:30
Chicago Midway (MDW)
Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:35, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN2211
14:00
Destin/Fort Walton Beach (VPS)

20:10
Chicago Midway (MDW)
Effective 2026-03-05 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 6:10, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN2211
14:00
Destin/Fort Walton Beach (VPS)

20:45
Chicago Midway (MDW)
Effective 2026-03-08 through 2026-04-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:45, 2-stop
Boeing 737-700 (Scimitar Winglets)
  • A domestic route departing from the Destin/Fort Walton Beach airport (VPS) and arriving at Chicago Midway airport (MDW).
  • The flight distance is 783 miles, or 1261 km.
  • The timezone of both the departure and the arrival airports is UTC-6 . Current time at both airports is (loading...).
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