All airlines flying from Chicago Midway (MDW) to Dallas Love Field (DAL).

Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Mon,Thu,Fri 10:00 Chicago Midway (MDW) 13:45 Dallas Love Field (DAL) 1
Southwest Airlines WN 4014 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-03-05 through 2026-04-06
Sat 10:05 Chicago Midway (MDW) 14:00 Dallas Love Field (DAL) 1
Southwest Airlines WN 4078 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-03-07 through 2026-04-04
Sat 13:00 Chicago Midway (MDW) 18:25 Dallas Love Field (DAL) 1
Southwest Airlines WN 4402 1-stop Boeing 737-700 (Scimitar Winglets) 5:25 Effective 2026-03-07 through 2026-04-04
Mon-Fri 13:30 Chicago Midway (MDW) 19:00 Dallas Love Field (DAL) 1
Southwest Airlines WN 4627 1-stop Boeing 737 MAX 8 (7M8) 5:30 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 13:30 Chicago Midway (MDW) 19:00 Dallas Love Field (DAL) 1
Southwest Airlines WN 4627 1-stop Boeing 737 MAX 8 (7M8) 5:30 Effective 2026-01-18 through 2026-01-23
Mon-Fri 13:30 Chicago Midway (MDW) 19:00 Dallas Love Field (DAL) 1
Southwest Airlines WN 4627 1-stop Boeing 737 MAX 8 (7M8) 5:30 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 13:30 Chicago Midway (MDW) 19:00 Dallas Love Field (DAL) 1
Southwest Airlines WN 4627 1-stop Boeing 737 MAX 8 (7M8) 5:30 Effective 2026-02-08 through 2026-02-11
Tue,Wed 13:30 Chicago Midway (MDW) 19:00 Dallas Love Field (DAL) 1
Southwest Airlines WN 4627 1-stop Boeing 737 MAX 8 (7M8) 5:30 Effective 2026-02-18 through 2026-03-04
Sat 14:30 Chicago Midway (MDW) 19:55 Dallas Love Field (DAL) 1
Southwest Airlines WN 4627 1-stop Boeing 737-800 (73H) 5:25 Effective 2026-02-14 through 2026-02-28
Sat 08:10 Chicago Midway (MDW) 14:45 Dallas Love Field (DAL) 1
Southwest Airlines WN 30 2-stop Boeing 737-700 (Scimitar Winglets) 6:35 Effective 2026-04-11 through 2026-05-30
Wed,Thu 08:25 Chicago Midway (MDW) 13:20 Dallas Love Field (DAL) 1
Southwest Airlines WN 31 2-stop Boeing 737-700 (73W) 4:55 Valid until 2026-01-01
Mon 16:10 Chicago Midway (MDW) 22:50 Dallas Love Field (DAL) 1
Southwest Airlines WN 295 2-stop Boeing 737-700 (Scimitar Winglets) 6:40 Operates only on 2026-01-05
Tue,Wed 08:10 Chicago Midway (MDW) 17:05 Dallas Love Field (DAL) 1
Southwest Airlines WN 1355 2-stop Boeing 737 MAX 8 (7M8) 8:55 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 09:45 Chicago Midway (MDW) 15:50 Dallas Love Field (DAL) 1
Southwest Airlines WN 2205 2-stop Boeing 737-700 (Scimitar Winglets) 6:05 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 09:45 Chicago Midway (MDW) 15:50 Dallas Love Field (DAL) 1
Southwest Airlines WN 2205 2-stop Boeing 737-700 (Scimitar Winglets) 6:05 Effective 2026-02-20 through 2026-03-01
Sat 13:20 Chicago Midway (MDW) 23:30 Dallas Love Field (DAL) 1
Southwest Airlines WN 2221 2-stop Boeing 737 MAX 8 (7M8) 10:10 Effective 2026-06-06 through 2026-08-01
Sat 09:45 Chicago Midway (MDW) 17:45 Dallas Love Field (DAL) 1
Southwest Airlines WN 2267 2-stop Boeing 737-700 (Scimitar Winglets) 8:00 Effective 2026-01-10 through 2026-02-07
Tue,Wed 10:10 Chicago Midway (MDW) 15:45 Dallas Love Field (DAL) 1
Southwest Airlines WN 2278 2-stop Boeing 737-700 (Scimitar Winglets) 5:35 Effective 2026-04-07 through 2026-06-03
Sun 07:40 Chicago Midway (MDW) 17:00 Dallas Love Field (DAL) 1
Southwest Airlines WN 2731 3-stop Boeing 737-800 (73H) 9:20 Effective 2026-06-07 through 2026-08-02
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All airlines flying from Chicago Midway (MDW) to Dallas Love Field (DAL).
Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Southwest Airlines WN4014
10:00
Chicago Midway (MDW)

13:45
Dallas Love Field (DAL) 1
Effective 2026-03-05 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4078
10:05
Chicago Midway (MDW)

14:00
Dallas Love Field (DAL) 1
Effective 2026-03-07 through 2026-04-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4402
13:00
Chicago Midway (MDW)

18:25
Dallas Love Field (DAL) 1
Effective 2026-03-07 through 2026-04-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:25, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4627
13:30
Chicago Midway (MDW)

19:00
Dallas Love Field (DAL) 1
Effective 2026-01-06 through 2026-01-14
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 5:30, 1-stop
Boeing 737 MAX 8 (7M8)
Non-Direct Flights:
Southwest Airlines WN4627
13:30
Chicago Midway (MDW)

19:00
Dallas Love Field (DAL) 1
Effective 2026-01-18 through 2026-01-23
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
Duration: 5:30, 1-stop
Boeing 737 MAX 8 (7M8)
Non-Direct Flights:
Southwest Airlines WN4627
13:30
Chicago Midway (MDW)

19:00
Dallas Love Field (DAL) 1
Effective 2026-01-26 through 2026-02-04
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 5:30, 1-stop
Boeing 737 MAX 8 (7M8)
Non-Direct Flights:
Southwest Airlines WN4627
13:30
Chicago Midway (MDW)

19:00
Dallas Love Field (DAL) 1
Effective 2026-02-08 through 2026-02-11
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:30, 1-stop
Boeing 737 MAX 8 (7M8)
Non-Direct Flights:
Southwest Airlines WN4627
13:30
Chicago Midway (MDW)

19:00
Dallas Love Field (DAL) 1
Effective 2026-02-18 through 2026-03-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:30, 1-stop
Boeing 737 MAX 8 (7M8)
Non-Direct Flights:
Southwest Airlines WN4627
14:30
Chicago Midway (MDW)

19:55
Dallas Love Field (DAL) 1
Effective 2026-02-14 through 2026-02-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:25, 1-stop
Boeing 737-800 (73H)
Non-Direct Flights:
Southwest Airlines WN30
08:10
Chicago Midway (MDW)

14:45
Dallas Love Field (DAL) 1
Effective 2026-04-11 through 2026-05-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:35, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN31
08:25
Chicago Midway (MDW)

13:20
Dallas Love Field (DAL) 1
Valid until 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:55, 2-stop
Boeing 737-700 (73W)
Non-Direct Flights:
Southwest Airlines WN295
16:10
Chicago Midway (MDW)

22:50
Dallas Love Field (DAL) 1
Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 6:40, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN1355
08:10
Chicago Midway (MDW)

17:05
Dallas Love Field (DAL) 1
Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 8:55, 2-stop
Boeing 737 MAX 8 (7M8)
Non-Direct Flights:
Southwest Airlines WN2205
09:45
Chicago Midway (MDW)

15:50
Dallas Love Field (DAL) 1
Effective 2026-02-12 through 2026-02-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 6:05, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN2205
09:45
Chicago Midway (MDW)

15:50
Dallas Love Field (DAL) 1
Effective 2026-02-20 through 2026-03-01
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 6:05, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN2221
13:20
Chicago Midway (MDW)

23:30
Dallas Love Field (DAL) 1
Effective 2026-06-06 through 2026-08-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 10:10, 2-stop
Boeing 737 MAX 8 (7M8)
Non-Direct Flights:
Southwest Airlines WN2267
09:45
Chicago Midway (MDW)

17:45
Dallas Love Field (DAL) 1
Effective 2026-01-10 through 2026-02-07
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 8:00, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN2278
10:10
Chicago Midway (MDW)

15:45
Dallas Love Field (DAL) 1
Effective 2026-04-07 through 2026-06-03
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:35, 2-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN2731
07:40
Chicago Midway (MDW)

17:00
Dallas Love Field (DAL) 1
Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 9:20, 3-stop
Boeing 737-800 (73H)
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  • A domestic route departing from the Chicago Midway airport (MDW) and arriving at Dallas Love Field airport (DAL).
  • The flight distance is 793 miles, or 1276 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 2:10 and 2:40.
Return (DAL-MDW) flights
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