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

Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
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 2025-09-07 through 2025-09-28
Mon-Wed 19:55 Love Field, Dallas (DAL) 1 23:20 Midway, Chicago (MDW)
Southwest Airlines WN 2227 1-stop Boeing 737-700 (Scimitar Winglets) 3:25 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 19:55 Love Field, Dallas (DAL) 1 23:20 Midway, Chicago (MDW)
Southwest Airlines WN 2227 1-stop Boeing 737-700 (Scimitar Winglets) 3:25 Effective 2025-12-19 through 2026-01-04
Sun 11:25 Love Field, Dallas (DAL) 1 15:45 Midway, Chicago (MDW)
Southwest Airlines WN 2252 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Operates only on 2025-11-30
Sat 16:15 Love Field, Dallas (DAL) 1 20:55 Midway, Chicago (MDW)
Southwest Airlines WN 2285 1-stop Boeing 737-700 (73W) 4:40 Effective 2025-06-07 through 2025-08-02
Sat 08:45 Love Field, Dallas (DAL) 1 12:10 Midway, Chicago (MDW)
Southwest Airlines WN 2323 1-stop Boeing 737-700 (73W) 3:25 Valid until 2025-05-31
Sat 11:55 Love Field, Dallas (DAL) 1 15:20 Midway, Chicago (MDW)
Southwest Airlines WN 2337 1-stop Boeing 737-700 (Scimitar Winglets) 3:25 Effective 2025-11-08 through 2025-11-15
Sat 11:55 Love Field, Dallas (DAL) 1 15:20 Midway, Chicago (MDW)
Southwest Airlines WN 2337 1-stop Boeing 737-700 (Scimitar Winglets) 3:25 Effective 2025-12-06 through 2025-12-13
Sun 10:05 Love Field, Dallas (DAL) 1 13:55 Midway, Chicago (MDW)
Southwest Airlines WN 2623 1-stop Boeing 737-700 (Scimitar Winglets) 3:50 Effective 2025-10-05 through 2025-10-26
Sun 08:50 Love Field, Dallas (DAL) 1 12:15 Midway, Chicago (MDW)
Southwest Airlines WN 2782 1-stop Boeing 737-700 (73W) 3:25 Valid until 2025-05-18
Sun 08:50 Love Field, Dallas (DAL) 1 12:15 Midway, Chicago (MDW)
Southwest Airlines WN 2782 1-stop Boeing 737-700 (73W) 3:25 Operates only on 2025-06-01
Mon,Thu,Fri 13:40 Love Field, Dallas (DAL) 1 17:35 Midway, Chicago (MDW)
Southwest Airlines WN 2800 1-stop Boeing 737 MAX 8 (7M8) 3:55 Valid until 2025-06-02
Sat 12:35 Love Field, Dallas (DAL) 1 16:35 Midway, Chicago (MDW)
Southwest Airlines WN 3076 1-stop Boeing 737-800 (73H) 4:00 Effective 2025-08-09 through 2025-09-27
Mon,Thu,Fri 13:40 Love Field, Dallas (DAL) 1 17:45 Midway, Chicago (MDW)
Southwest Airlines WN 3076 1-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2025-08-07 through 2025-09-29
Sun 10:25 Love Field, Dallas (DAL) 1 14:05 Midway, Chicago (MDW)
Southwest Airlines WN 3267 1-stop Boeing 737-700 (73W) 3:40 Operates only on 2025-08-31
Tue,Wed 15:45 Love Field, Dallas (DAL) 1 19:25 Midway, Chicago (MDW)
Southwest Airlines WN 3321 1-stop Boeing 737-700 (73W) 3:40 Effective 2025-08-05 through 2025-10-01
Sat 15:30 Love Field, Dallas (DAL) 1 19:50 Midway, Chicago (MDW)
Southwest Airlines WN 3384 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-11-22 through 2025-11-29
Sat 15:30 Love Field, Dallas (DAL) 1 19:50 Midway, Chicago (MDW)
Southwest Airlines WN 3384 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-12-20 through 2026-01-03
Sat 12:55 Love Field, Dallas (DAL) 1 16:40 Midway, Chicago (MDW)
Southwest Airlines WN 3389 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-11-08 through 2025-11-15
Sat 12:55 Love Field, Dallas (DAL) 1 16:40 Midway, Chicago (MDW)
Southwest Airlines WN 3389 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2025-12-06 through 2025-12-13
Tue,Wed 13:55 Love Field, Dallas (DAL) 1 18:10 Midway, Chicago (MDW)
Southwest Airlines WN 3570 1-stop Boeing 737-700 (73W) 4:15 Effective 2025-06-10 through 2025-07-30
Fri 13:05 Love Field, Dallas (DAL) 1 18:20 Midway, Chicago (MDW)
Southwest Airlines WN 3827 1-stop Boeing 737 MAX 8 (7M8) 5:15 Operates only on 2025-07-04
Sun 11:00 Love Field, Dallas (DAL) 1 14:50 Midway, Chicago (MDW)
Southwest Airlines WN 3935 1-stop Boeing 737-700 (73W) 3:50 Valid until 2025-05-18
Sun 11:00 Love Field, Dallas (DAL) 1 14:50 Midway, Chicago (MDW)
Southwest Airlines WN 3935 1-stop Boeing 737-700 (73W) 3:50 Operates only on 2025-06-01
Mon,Thu,Fri 07:50 Love Field, Dallas (DAL) 1 11:25 Midway, Chicago (MDW)
Southwest Airlines WN 4131 1-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2025-10-02 through 2025-10-31
Tue,Wed 13:05 Love Field, Dallas (DAL) 1 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 4174 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-10-07 through 2025-10-29
Sun 08:50 Love Field, Dallas (DAL) 1 12:35 Midway, Chicago (MDW)
Southwest Airlines WN 4331 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Operates only on 2025-11-30
Sat 11:30 Love Field, Dallas (DAL) 1 15:00 Midway, Chicago (MDW)
Southwest Airlines WN 4663 1-stop Boeing 737 MAX 8 (7M8) 3:30 Effective 2025-06-07 through 2025-08-02
Sun 09:50 Love Field, Dallas (DAL) 1 16:45 Midway, Chicago (MDW)
Southwest Airlines WN 15 2-stop Boeing 737-700 (73W) 6:55 Effective 2025-08-10 through 2025-08-24
Sun 09:50 Love Field, Dallas (DAL) 1 16:45 Midway, Chicago (MDW)
Southwest Airlines WN 15 2-stop Boeing 737-700 (73W) 6:55 Effective 2025-09-07 through 2025-09-28
Tue,Wed 12:10 Love Field, Dallas (DAL) 1 19:35 Midway, Chicago (MDW)
Southwest Airlines WN 547 2-stop Boeing 737 MAX 8 (7M8) 7:25 Effective 2025-10-07 through 2025-10-29
Sun 11:30 Love Field, Dallas (DAL) 1 18:40 Midway, Chicago (MDW)
Southwest Airlines WN 2476 2-stop Boeing 737-700 (Scimitar Winglets) 7:10 Effective 2025-10-05 through 2025-10-26
Tue,Wed 11:25 Love Field, Dallas (DAL) 1 18:30 Midway, Chicago (MDW)
Southwest Airlines WN 4081 2-stop Boeing 737-700 (Scimitar Winglets) 7:05 Effective 2025-10-07 through 2025-10-29
Mon,Thu,Fri,Sun 08:20 Love Field, Dallas (DAL) 1 19:05 Midway, Chicago (MDW)
Southwest Airlines WN 1419 3-stop Boeing 737-700 (Scimitar Winglets) 10:45 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 08:20 Love Field, Dallas (DAL) 1 19:05 Midway, Chicago (MDW)
Southwest Airlines WN 1419 3-stop Boeing 737-700 (Scimitar Winglets) 10:45 Effective 2025-11-21 through 2025-11-28
Fri,Sun 08:20 Love Field, Dallas (DAL) 1 19:05 Midway, Chicago (MDW)
Southwest Airlines WN 1419 3-stop Boeing 737-700 (Scimitar Winglets) 10:45 Effective 2025-12-07 through 2025-12-14
Thu 08:20 Love Field, Dallas (DAL) 1 19:05 Midway, Chicago (MDW)
Southwest Airlines WN 1419 3-stop Boeing 737-700 (Scimitar Winglets) 10:45 Operates only on 2025-12-18
Mon 08:20 Love Field, Dallas (DAL) 1 19:05 Midway, Chicago (MDW)
Southwest Airlines WN 1419 3-stop Boeing 737-700 (Scimitar Winglets) 10:45 Operates only on 2026-01-05
Sun 11:00 Love Field, Dallas (DAL) 1 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 2062 3-stop Boeing 737-700 (Scimitar Winglets) 8:30 Effective 2025-10-05 through 2025-10-26
Sat 09:10 Love Field, Dallas (DAL) 1 19:35 Midway, Chicago (MDW)
Southwest Airlines WN 2754 3-stop Boeing 737-700 (73W) 10:25 Valid until 2025-05-31
Mon,Thu,Fri 07:35 Love Field, Dallas (DAL) 1 19:05 Midway, Chicago (MDW)
Southwest Airlines WN 3826 4-stop Boeing 737-700 (73W) 11:30 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 07:35 Love Field, Dallas (DAL) 1 19:05 Midway, Chicago (MDW)
Southwest Airlines WN 3826 4-stop Boeing 737-700 (73W) 11:30 Effective 2025-07-07 through 2025-08-04
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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 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:15, 1-stop
Boeing 737-700 (73W)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 3:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-06-07 through 2025-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:40, 1-stop
Boeing 737-700 (73W)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:25, 1-stop
Boeing 737-700 (73W)

Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-05 through 2025-10-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:50, 1-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:25, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:25, 1-stop
Boeing 737-700 (73W)

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-08-09 through 2025-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, 1-stop
Boeing 737-800 (73H)

Effective 2025-08-07 through 2025-09-29
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:05, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-08-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:40, 1-stop
Boeing 737-700 (73W)

Effective 2025-08-05 through 2025-10-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:40, 1-stop
Boeing 737-700 (73W)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-20 through 2026-01-03
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: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:15, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-07-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 5:15, 1-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:50, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:50, 1-stop
Boeing 737-700 (73W)

Effective 2025-10-02 through 2025-10-31
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:35, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-07 through 2025-10-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-06-07 through 2025-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:30, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:55, 2-stop
Boeing 737-700 (73W)

Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:55, 2-stop
Boeing 737-700 (73W)

Effective 2025-10-07 through 2025-10-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 7:25, 2-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-10-05 through 2025-10-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 7:10, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-07 through 2025-10-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 7:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 10:45, 3-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 10:45, 3-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 10:45, 3-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 10:45, 3-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 10:45, 3-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-05 through 2025-10-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 8:30, 3-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 10:25, 3-stop
Boeing 737-700 (73W)

Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 11:30, 4-stop
Boeing 737-700 (73W)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 11:30, 4-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.