All airlines flying from Destin/Fort Walton Beach (VPS) to Chicago Midway (MDW).

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sun 12:31 Destin/Fort Walton Beach (VPS) 14:50 Chicago Midway (MDW)
Allegiant Air G4 1450 Non-stop Airbus A319 (319) 2:19 Effective 2026-02-15 through 2026-03-01
Thu,Sun 14:40 Destin/Fort Walton Beach (VPS) 16:57 Chicago Midway (MDW)
Allegiant Air G4 1450 Non-stop Airbus A319 (319) 2:17 Effective 2026-04-02 through 2026-05-17
Thu 17:37 Destin/Fort Walton Beach (VPS) 19:53 Chicago Midway (MDW)
Allegiant Air G4 1450 Non-stop Airbus A319 (319) 2:16 Operates only on 2026-03-12
Thu 17:37 Destin/Fort Walton Beach (VPS) 19:53 Chicago Midway (MDW)
Allegiant Air G4 1450 Non-stop Airbus A319 (319) 2:16 Operates only on 2026-03-26
Thu,Sun 18:07 Destin/Fort Walton Beach (VPS) 20:23 Chicago Midway (MDW)
Allegiant Air G4 1450 Non-stop Airbus A319 (319) 2:16 Effective 2026-03-19 through 2026-03-22
Fri 18:21 Destin/Fort Walton Beach (VPS) 20:40 Chicago Midway (MDW)
Allegiant Air G4 1458 Non-stop Airbus A320 (320) 2:19 Effective 2026-05-22 through 2026-05-29
Mon,Fri 18:05 Destin/Fort Walton Beach (VPS) 20:25 Chicago Midway (MDW)
Allegiant Air G4 1480 Non-stop Airbus A320 (320) 2:20 Effective 2026-07-03 through 2026-08-03
Mon 18:12 Destin/Fort Walton Beach (VPS) 20:33 Chicago Midway (MDW)
Allegiant Air G4 1480 Non-stop Airbus A320 (320) 2:21 Effective 2026-06-08 through 2026-06-29
Fri 18:14 Destin/Fort Walton Beach (VPS) 20:35 Chicago Midway (MDW)
Allegiant Air G4 1480 Non-stop Airbus A320 (320) 2:21 Effective 2026-08-07 through 2026-08-14
Mon 18:21 Destin/Fort Walton Beach (VPS) 20:40 Chicago Midway (MDW)
Allegiant Air G4 1480 Non-stop Airbus A320 (320) 2:19 Effective 2026-05-25 through 2026-06-01
Mon 18:14 Destin/Fort Walton Beach (VPS) 20:35 Chicago Midway (MDW)
Allegiant Air G4 1485 Non-stop Airbus A320 (320) 2:21 Effective 2026-08-10 through 2026-08-17
Fri 18:12 Destin/Fort Walton Beach (VPS) 20:33 Chicago Midway (MDW)
Allegiant Air G4 1490 Non-stop Airbus A320 (320) 2:21 Effective 2026-06-05 through 2026-06-26
Thu 12:31 Destin/Fort Walton Beach (VPS) 14:50 Chicago Midway (MDW)
Allegiant Air G4 1493 Non-stop Airbus A319 (319) 2:19 Operates only on 2026-02-26
Thu 13:01 Destin/Fort Walton Beach (VPS) 15:20 Chicago Midway (MDW)
Allegiant Air G4 1493 Non-stop Airbus A319 (319) 2:19 Effective 2026-02-12 through 2026-02-19
Sun 17:40 Destin/Fort Walton Beach (VPS) 19:56 Chicago Midway (MDW)
Allegiant Air G4 1493 Non-stop Airbus A319 (319) 2:16 Operates only on 2026-03-08
Sat 11:01 Destin/Fort Walton Beach (VPS) 13:20 Chicago Midway (MDW)
Allegiant Air G4 3074 Non-stop Airbus A319 (319) 2:19 Valid until 2026-01-03
Thu 17:40 Destin/Fort Walton Beach (VPS) 19:56 Chicago Midway (MDW)
Allegiant Air G4 3097 Non-stop Airbus A319 (319) 2:16 Operates only on 2026-03-05
Sun 17:37 Destin/Fort Walton Beach (VPS) 19:53 Chicago Midway (MDW)
Allegiant Air G4 3117 Non-stop Airbus A319 (319) 2:16 Operates only on 2026-03-15
Sun 17:37 Destin/Fort Walton Beach (VPS) 19:53 Chicago Midway (MDW)
Allegiant Air G4 3117 Non-stop Airbus A319 (319) 2:16 Operates only on 2026-03-29
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


All airlines flying from Destin/Fort Walton Beach (VPS) to Chicago Midway (MDW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2026-02-15 through 2026-03-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:19, non-stop
Airbus A319 (319)

Direct Flights:

Effective 2026-04-02 through 2026-05-17
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
Duration: 2:17, non-stop
Airbus A319 (319)

Direct Flights:

Operates only on 2026-03-12
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:16, non-stop
Airbus A319 (319)

Direct Flights:

Operates only on 2026-03-26
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:16, non-stop
Airbus A319 (319)

Direct Flights:

Effective 2026-03-19 through 2026-03-22
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
Duration: 2:16, non-stop
Airbus A319 (319)

Direct Flights:

Effective 2026-05-22 through 2026-05-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 2:19, non-stop
Airbus A320 (320)

Direct Flights:

Effective 2026-07-03 through 2026-08-03
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Airbus A320 (320)

Direct Flights:

Effective 2026-06-08 through 2026-06-29
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:21, non-stop
Airbus A320 (320)

Direct Flights:

Effective 2026-08-07 through 2026-08-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 2:21, non-stop
Airbus A320 (320)

Direct Flights:

Effective 2026-05-25 through 2026-06-01
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:19, non-stop
Airbus A320 (320)

Direct Flights:

Effective 2026-08-10 through 2026-08-17
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:21, non-stop
Airbus A320 (320)

Direct Flights:

Effective 2026-06-05 through 2026-06-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 2:21, non-stop
Airbus A320 (320)

Direct Flights:

Operates only on 2026-02-26
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:19, non-stop
Airbus A319 (319)

Direct Flights:

Effective 2026-02-12 through 2026-02-19
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:19, non-stop
Airbus A319 (319)

Direct Flights:

Operates only on 2026-03-08
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:16, non-stop
Airbus A319 (319)

Direct Flights:

Valid until 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:19, non-stop
Airbus A319 (319)

Direct Flights:

Operates only on 2026-03-05
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:16, non-stop
Airbus A319 (319)

Direct Flights:

Operates only on 2026-03-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:16, non-stop
Airbus A319 (319)

Direct Flights:

Operates only on 2026-03-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:16, non-stop
Airbus A319 (319)

Non-Direct Flights:

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:

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:

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:

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:

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:

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...).
  • For direct flights, the flight time varies between 2:16 and 2:21.