Southwest Airlines flights from Love Field, Dallas (DAL) to Midway, Chicago (MDW).

Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Mon,Fri,Sun 10:00 Love Field, Dallas (DAL) 1 14:15 Midway, Chicago (MDW)
Southwest Airlines WN 15 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Effective 2025-11-21 through 2025-11-28
Fri,Sun 10:00 Love Field, Dallas (DAL) 1 14:15 Midway, Chicago (MDW)
Southwest Airlines WN 15 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Effective 2025-12-07 through 2025-12-14
Thu 10:00 Love Field, Dallas (DAL) 1 14:15 Midway, Chicago (MDW)
Southwest Airlines WN 15 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Operates only on 2025-12-18
Mon 10:00 Love Field, Dallas (DAL) 1 14:15 Midway, Chicago (MDW)
Southwest Airlines WN 15 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Operates only on 2026-01-05
Tue,Wed 13:20 Love Field, Dallas (DAL) 1 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 22 1-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2025-11-04 through 2025-11-12
Mon-Thu 13:20 Love Field, Dallas (DAL) 1 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 22 1-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2025-11-17 through 2025-11-20
Mon-Fri 13:20 Love Field, Dallas (DAL) 1 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 22 1-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2025-12-02 through 2025-12-11
Mon-Wed 13:20 Love Field, Dallas (DAL) 1 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 22 1-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2025-12-15 through 2025-12-17
Wed,Thu 13:20 Love Field, Dallas (DAL) 1 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 22 1-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2025-12-24 through 2026-01-01
Sun 19:35 Love Field, Dallas (DAL) 1 23:50 Midway, Chicago (MDW)
Southwest Airlines WN 27 1-stop Boeing 737-700 (73W) 4:15 Effective 2025-06-08 through 2025-08-03
Tue,Wed 15:35 Love Field, Dallas (DAL) 1 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 126 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-11-04 through 2025-11-12
Mon-Thu 15:35 Love Field, Dallas (DAL) 1 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 126 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-11-17 through 2025-11-20
Mon-Fri 15:35 Love Field, Dallas (DAL) 1 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 126 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-12-02 through 2025-12-11
Mon-Wed 15:35 Love Field, Dallas (DAL) 1 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 126 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-12-15 through 2025-12-17
Wed,Thu 15:35 Love Field, Dallas (DAL) 1 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 126 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-12-24 through 2026-01-01
Mon,Thu,Fri,Sun 08:25 Love Field, Dallas (DAL) 1 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 209 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 08:25 Love Field, Dallas (DAL) 1 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 209 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-11-21 through 2025-11-28
Fri,Sun 08:25 Love Field, Dallas (DAL) 1 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 209 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-12-07 through 2025-12-14
Thu 08:25 Love Field, Dallas (DAL) 1 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 209 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Operates only on 2025-12-18
Mon 08:25 Love Field, Dallas (DAL) 1 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 209 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Operates only on 2026-01-05
Sat 12:25 Love Field, Dallas (DAL) 1 16:45 Midway, Chicago (MDW)
Southwest Airlines WN 209 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-11-08 through 2025-11-15
Sat 12:25 Love Field, Dallas (DAL) 1 16:45 Midway, Chicago (MDW)
Southwest Airlines WN 209 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-12-06 through 2025-12-13
Sun 11:40 Love Field, Dallas (DAL) 1 15:35 Midway, Chicago (MDW)
Southwest Airlines WN 237 1-stop Boeing 737-800 (73H) 3:55 Operates only on 2025-08-31
Sun 08:45 Love Field, Dallas (DAL) 1 12:30 Midway, Chicago (MDW)
Southwest Airlines WN 247 1-stop Boeing 737-700 (73W) 3:45 Operates only on 2025-05-25
Mon,Thu,Fri 08:55 Love Field, Dallas (DAL) 1 13:40 Midway, Chicago (MDW)
Southwest Airlines WN 311 1-stop Boeing 737-700 (73W) 4:45 Effective 2025-08-07 through 2025-09-29
Sun 15:20 Love Field, Dallas (DAL) 1 19:40 Midway, Chicago (MDW)
Southwest Airlines WN 404 1-stop Boeing 737-800 (73H) 4:20 Operates only on 2025-05-25
Fri 09:20 Love Field, Dallas (DAL) 1 13:20 Midway, Chicago (MDW)
Southwest Airlines WN 715 1-stop Boeing 737 MAX 8 (7M8) 4:00 Operates only on 2025-07-04
Tue,Wed 14:20 Love Field, Dallas (DAL) 1 19:55 Midway, Chicago (MDW)
Southwest Airlines WN 762 1-stop Boeing 737-800 (73H) 5:35 Valid until 2025-06-04
Mon-Wed 13:55 Love Field, Dallas (DAL) 1 17:55 Midway, Chicago (MDW)
Southwest Airlines WN 770 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 13:55 Love Field, Dallas (DAL) 1 17:55 Midway, Chicago (MDW)
Southwest Airlines WN 770 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2025-12-19 through 2026-01-04
Sun 08:50 Love Field, Dallas (DAL) 1 12:15 Midway, Chicago (MDW)
Southwest Airlines WN 884 1-stop Boeing 737-700 (Scimitar Winglets) 3:25 Operates only on 2025-11-30
Mon,Thu,Fri,Sun 14:20 Love Field, Dallas (DAL) 1 18:25 Midway, Chicago (MDW)
Southwest Airlines WN 924 1-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 14:20 Love Field, Dallas (DAL) 1 18:25 Midway, Chicago (MDW)
Southwest Airlines WN 924 1-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-11-21 through 2025-11-28
Fri,Sun 14:20 Love Field, Dallas (DAL) 1 18:25 Midway, Chicago (MDW)
Southwest Airlines WN 924 1-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-12-07 through 2025-12-14
Thu 14:20 Love Field, Dallas (DAL) 1 18:25 Midway, Chicago (MDW)
Southwest Airlines WN 924 1-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2025-12-18
Mon 14:20 Love Field, Dallas (DAL) 1 18:25 Midway, Chicago (MDW)
Southwest Airlines WN 924 1-stop Boeing 737 MAX 8 (7M8) 4:05 Operates only on 2026-01-05
Mon-Wed 14:50 Love Field, Dallas (DAL) 1 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 924 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 14:50 Love Field, Dallas (DAL) 1 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 924 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2025-12-19 through 2026-01-04
Sat 14:25 Love Field, Dallas (DAL) 1 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 980 1-stop Boeing 737-700 (73W) 4:30 Effective 2025-08-09 through 2025-09-27
Sat 12:15 Love Field, Dallas (DAL) 1 16:40 Midway, Chicago (MDW)
Southwest Airlines WN 1192 1-stop Boeing 737-700 (Scimitar Winglets) 4:25 Effective 2025-10-04 through 2025-11-01
Sat 09:00 Love Field, Dallas (DAL) 1 13:30 Midway, Chicago (MDW)
Southwest Airlines WN 1635 1-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2025-11-22 through 2025-11-29
Sat 09:00 Love Field, Dallas (DAL) 1 13:30 Midway, Chicago (MDW)
Southwest Airlines WN 1635 1-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2025-12-20 through 2026-01-03
Mon,Thu,Fri 13:25 Love Field, Dallas (DAL) 1 17:40 Midway, Chicago (MDW)
Southwest Airlines WN 1882 1-stop Boeing 737-800 (73H) 4:15 Valid until 2025-06-02
Sat 10:10 Love Field, Dallas (DAL) 1 13:50 Midway, Chicago (MDW)
Southwest Airlines WN 1888 1-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2025-11-22 through 2025-11-29
Sat 10:10 Love Field, Dallas (DAL) 1 13:50 Midway, Chicago (MDW)
Southwest Airlines WN 1888 1-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2025-12-20 through 2026-01-03
Sun 15:25 Love Field, Dallas (DAL) 1 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 1935 1-stop Boeing 737-700 (73W) 4:05 Effective 2025-08-10 through 2025-08-24
Sun 15:25 Love Field, Dallas (DAL) 1 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 1935 1-stop Boeing 737-700 (73W) 4:05 Effective 2025-09-07 through 2025-09-28
Tue,Wed 13:40 Love Field, Dallas (DAL) 1 17:25 Midway, Chicago (MDW)
Southwest Airlines WN 1968 1-stop Boeing 737-700 (73W) 3:45 Valid until 2025-06-04
Sun 07:10 Love Field, Dallas (DAL) 1 11:45 Midway, Chicago (MDW)
Southwest Airlines WN 2108 1-stop Boeing 737-700 (Scimitar Winglets) 4:35 Operates only on 2025-11-30
Sun 16:20 Love Field, Dallas (DAL) 1 21:35 Midway, Chicago (MDW)
Southwest Airlines WN 2138 1-stop Boeing 737-700 (73W) 5:15 Effective 2025-08-10 through 2025-08-24
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Southwest Airlines flights from Love Field, Dallas (DAL) to Midway, Chicago (MDW).
Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:

Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-04 through 2025-11-12
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-17 through 2025-11-20
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-02 through 2025-12-11
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 3:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-15 through 2025-12-17
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-24 through 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:15, 1-stop
Boeing 737-700 (73W)

Effective 2025-11-04 through 2025-11-12
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-17 through 2025-11-20
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-02 through 2025-12-11
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-15 through 2025-12-17
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-24 through 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-08-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, 1-stop
Boeing 737-800 (73H)

Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:45, 1-stop
Boeing 737-700 (73W)

Effective 2025-08-07 through 2025-09-29
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:45, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:20, 1-stop
Boeing 737-800 (73H)

Operates only on 2025-07-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 4:00, 1-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:35, 1-stop
Boeing 737-800 (73H)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-08-09 through 2025-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:30, 1-stop
Boeing 737-700 (73W)

Effective 2025-10-04 through 2025-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:15, 1-stop
Boeing 737-800 (73H)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:05, 1-stop
Boeing 737-700 (73W)

Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:45, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:35, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:15, 1-stop
Boeing 737-700 (73W)
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  • A domestic route departing from the Love Field, Dallas airport (DAL) and arriving at Midway, Chicago airport (MDW).
  • 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 2:20.