All airlines flying from Detroit (DTW) to Chicago Midway (MDW).

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 13:25 Detroit (DTW) E 13:35 Chicago Midway (MDW)
Southwest Airlines WN 459 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-03-05 through 2026-04-06
Tue,Wed 14:15 Detroit (DTW) E 14:30 Chicago Midway (MDW)
Southwest Airlines WN 459 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-03-10 through 2026-04-01
Mon-Fri 13:25 Detroit (DTW) E 13:35 Chicago Midway (MDW)
Southwest Airlines WN 507 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-06-04 through 2026-08-03
Sun 12:55 Detroit (DTW) E 13:05 Chicago Midway (MDW)
Southwest Airlines WN 577 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 12:55 Detroit (DTW) E 13:05 Chicago Midway (MDW)
Southwest Airlines WN 878 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-04-09 through 2026-06-01
Tue,Wed 13:40 Detroit (DTW) E 13:50 Chicago Midway (MDW)
Southwest Airlines WN 878 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-04-07 through 2026-06-03
Thu,Fri,Sun 19:35 Detroit (DTW) E 19:45 Chicago Midway (MDW)
Southwest Airlines WN 1118 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-01-11 through 2026-01-16
Mon,Sun 19:35 Detroit (DTW) E 19:45 Chicago Midway (MDW)
Southwest Airlines WN 1118 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 19:35 Detroit (DTW) E 19:45 Chicago Midway (MDW)
Southwest Airlines WN 1118 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-02-01 through 2026-02-06
Mon,Sun 19:35 Detroit (DTW) E 19:45 Chicago Midway (MDW)
Southwest Airlines WN 1118 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 19:35 Detroit (DTW) E 19:45 Chicago Midway (MDW)
Southwest Airlines WN 1118 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-02-17 through 2026-02-23
Mon 19:35 Detroit (DTW) E 19:45 Chicago Midway (MDW)
Southwest Airlines WN 1118 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Operates only on 2026-03-02
Sun 20:15 Detroit (DTW) E 20:30 Chicago Midway (MDW)
Southwest Airlines WN 1422 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 20:25 Detroit (DTW) E 20:40 Chicago Midway (MDW)
Southwest Airlines WN 1422 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-03-05 through 2026-04-06
Fri,Sun 12:45 Detroit (DTW) E 12:55 Chicago Midway (MDW)
Southwest Airlines WN 1668 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-01-02 through 2026-01-04
Sun 08:10 Detroit (DTW) E 08:20 Chicago Midway (MDW)
Southwest Airlines WN 1725 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-08-09 through 2026-09-27
Tue,Wed 08:45 Detroit (DTW) E 09:00 Chicago Midway (MDW)
Southwest Airlines WN 1725 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 08:55 Detroit (DTW) E 09:15 Chicago Midway (MDW)
Southwest Airlines WN 1725 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-08-06 through 2026-09-28
Tue,Wed 12:55 Detroit (DTW) E 13:05 Chicago Midway (MDW)
Southwest Airlines WN 1726 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-08-04 through 2026-09-30
Sun 08:10 Detroit (DTW) E 08:20 Chicago Midway (MDW)
Southwest Airlines WN 1781 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 08:40 Detroit (DTW) E 08:55 Chicago Midway (MDW)
Southwest Airlines WN 1781 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-06-04 through 2026-08-03
Tue,Wed 08:55 Detroit (DTW) E 09:10 Chicago Midway (MDW)
Southwest Airlines WN 1781 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-06-09 through 2026-07-29
Sat 19:20 Detroit (DTW) E 19:30 Chicago Midway (MDW)
Southwest Airlines WN 1782 Non-stop Boeing 737-800 (73H) 1:10 Effective 2026-06-06 through 2026-08-01
Tue,Wed 19:50 Detroit (DTW) E 20:05 Chicago Midway (MDW)
Southwest Airlines WN 1782 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-06-09 through 2026-07-29
Sun 20:25 Detroit (DTW) E 20:35 Chicago Midway (MDW)
Southwest Airlines WN 1782 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 20:30 Detroit (DTW) E 20:40 Chicago Midway (MDW)
Southwest Airlines WN 1782 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-06-04 through 2026-08-03
Sat 17:05 Detroit (DTW) E 17:15 Chicago Midway (MDW)
Southwest Airlines WN 1853 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-04-11 through 2026-05-30
Sun 15:15 Detroit (DTW) E 15:25 Chicago Midway (MDW)
Southwest Airlines WN 1875 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-08-09 through 2026-09-27
Mon,Thu,Fri 13:20 Detroit (DTW) E 13:30 Chicago Midway (MDW)
Southwest Airlines WN 2135 Non-stop Boeing 737-800 (73H) 1:10 Effective 2026-08-06 through 2026-09-28
Sun 19:30 Detroit (DTW) E 19:40 Chicago Midway (MDW)
Southwest Airlines WN 2141 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Operates only on 2026-05-24
Tue,Wed 19:40 Detroit (DTW) E 19:50 Chicago Midway (MDW)
Southwest Airlines WN 2141 Non-stop Boeing 737-800 (73H) 1:10 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 20:30 Detroit (DTW) E 20:45 Chicago Midway (MDW)
Southwest Airlines WN 2141 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-04-09 through 2026-06-01
Fri,Sun 21:15 Detroit (DTW) E 21:25 Chicago Midway (MDW)
Southwest Airlines WN 2373 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-01-02 through 2026-01-04
Tue,Wed 08:15 Detroit (DTW) E 08:30 Chicago Midway (MDW)
Southwest Airlines WN 2587 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-04-07 through 2026-06-03
Sun 08:25 Detroit (DTW) E 08:40 Chicago Midway (MDW)
Southwest Airlines WN 2587 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-04-12 through 2026-05-17
Sun 08:25 Detroit (DTW) E 08:40 Chicago Midway (MDW)
Southwest Airlines WN 2587 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Operates only on 2026-05-31
Sat 08:35 Detroit (DTW) E 08:55 Chicago Midway (MDW)
Southwest Airlines WN 2587 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-04-11 through 2026-05-30
Mon,Thu,Fri 08:45 Detroit (DTW) E 09:05 Chicago Midway (MDW)
Southwest Airlines WN 2587 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-04-09 through 2026-06-01
Sun 09:35 Detroit (DTW) E 09:45 Chicago Midway (MDW)
Southwest Airlines WN 2587 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Operates only on 2026-05-24
Mon 12:25 Detroit (DTW) E 12:35 Chicago Midway (MDW)
Southwest Airlines WN 2712 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Operates only on 2026-01-05
Wed,Thu 12:55 Detroit (DTW) E 13:05 Chicago Midway (MDW)
Southwest Airlines WN 2712 Non-stop Boeing 737-700 (73W) 1:10 Valid until 2026-01-01
Sun 15:45 Detroit (DTW) E 16:00 Chicago Midway (MDW)
Southwest Airlines WN 2851 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-04-12 through 2026-04-26
Sun 15:45 Detroit (DTW) E 16:00 Chicago Midway (MDW)
Southwest Airlines WN 2851 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-05-10 through 2026-05-17
Sun 15:45 Detroit (DTW) E 16:00 Chicago Midway (MDW)
Southwest Airlines WN 2851 Non-stop Boeing 737-800 (73H) 1:15 Operates only on 2026-05-31
Sun 15:50 Detroit (DTW) E 16:05 Chicago Midway (MDW)
Southwest Airlines WN 2851 Non-stop Boeing 737-800 (73H) 1:15 Operates only on 2026-05-03
Sat 08:10 Detroit (DTW) E 08:25 Chicago Midway (MDW)
Southwest Airlines WN 2861 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 08:25 Detroit (DTW) E 08:45 Chicago Midway (MDW)
Southwest Airlines WN 2861 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-03-05 through 2026-04-06
Sun 08:40 Detroit (DTW) E 09:00 Chicago Midway (MDW)
Southwest Airlines WN 2861 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-03-08 through 2026-04-05
Tue,Wed 08:45 Detroit (DTW) E 09:05 Chicago Midway (MDW)
Southwest Airlines WN 2861 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-03-10 through 2026-04-01
Mon,Tue,Fri,Sun 06:35 Detroit (DTW) E 06:55 Chicago Midway (MDW)
Southwest Airlines WN 2872 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Valid until 2026-01-04
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All airlines flying from Detroit (DTW) to Chicago Midway (MDW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2026-03-05 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-03-10 through 2026-04-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-04 through 2026-08-03
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-09 through 2026-06-01
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-07 through 2026-06-03
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-11 through 2026-01-16
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-19 through 2026-01-25
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-01 through 2026-02-06
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-09 through 2026-02-15
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-17 through 2026-02-23
Mon
Tue
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Operates only on 2026-03-02
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-03-08 through 2026-04-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-03-05 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-02 through 2026-01-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-06-04 through 2026-08-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-06-06 through 2026-08-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 1:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-04 through 2026-08-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-11 through 2026-05-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 1:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Operates only on 2026-05-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-07 through 2026-06-03
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-04-09 through 2026-06-01
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 1:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-01-02 through 2026-01-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-04-07 through 2026-06-03
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-04-12 through 2026-05-17
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Operates only on 2026-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-04-11 through 2026-05-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-04-09 through 2026-06-01
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Operates only on 2026-05-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Valid until 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 1:10, non-stop
Boeing 737-700 (73W)

Direct Flights:

Effective 2026-04-12 through 2026-04-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-05-10 through 2026-05-17
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Operates only on 2026-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Operates only on 2026-05-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-03-07 through 2026-04-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 1:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-03-05 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-03-08 through 2026-04-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-03-10 through 2026-04-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Valid until 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)
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  • A domestic route departing from the Detroit airport (DTW) and arriving at Chicago Midway airport (MDW).
  • The flight distance is 228 miles, or 367 km.
  • The timezone of the departure airport is UTC-5 , and the timezone of the arrival airport is UTC-6 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
  • For direct flights, the flight time varies between 1:10 and 1:40.