All airlines flying from Houston Hobby (HOU) to Midway, Chicago (MDW).

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Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Sun 14:10 Houston Hobby (HOU) 18:05 Midway, Chicago (MDW)
Southwest Airlines WN 3639 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-10-05 through 2025-10-26
Sun 13:55 Houston Hobby (HOU) 19:20 Midway, Chicago (MDW)
Southwest Airlines WN 3661 1-stop Boeing 737-700 (73W) 5:25 Valid until 2025-05-18
Sun 13:55 Houston Hobby (HOU) 19:20 Midway, Chicago (MDW)
Southwest Airlines WN 3661 1-stop Boeing 737-700 (73W) 5:25 Operates only on 2025-06-01
Tue,Wed 11:30 Houston Hobby (HOU) 15:30 Midway, Chicago (MDW)
Southwest Airlines WN 3787 1-stop Boeing 737-800 (73H) 4:00 Effective 2025-08-05 through 2025-10-01
Sun 16:15 Houston Hobby (HOU) 21:25 Midway, Chicago (MDW)
Southwest Airlines WN 3827 1-stop Boeing 737-700 (73W) 5:10 Effective 2025-06-08 through 2025-08-03
Sat 15:35 Houston Hobby (HOU) 20:45 Midway, Chicago (MDW)
Southwest Airlines WN 4780 1-stop Boeing 737-700 (73W) 5:10 Effective 2025-06-07 through 2025-08-02
Tue,Wed 11:30 Houston Hobby (HOU) 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 22 2-stop Boeing 737-700 (Scimitar Winglets) 5:30 Effective 2025-11-04 through 2025-11-12
Mon-Thu 11:30 Houston Hobby (HOU) 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 22 2-stop Boeing 737-700 (Scimitar Winglets) 5:30 Effective 2025-11-17 through 2025-11-20
Mon-Fri 11:30 Houston Hobby (HOU) 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 22 2-stop Boeing 737-700 (Scimitar Winglets) 5:30 Effective 2025-12-02 through 2025-12-11
Mon-Wed 11:30 Houston Hobby (HOU) 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 22 2-stop Boeing 737-700 (Scimitar Winglets) 5:30 Effective 2025-12-15 through 2025-12-17
Wed,Thu 11:30 Houston Hobby (HOU) 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 22 2-stop Boeing 737-700 (Scimitar Winglets) 5:30 Effective 2025-12-24 through 2026-01-01
Sun 12:55 Houston Hobby (HOU) 22:10 Midway, Chicago (MDW)
Southwest Airlines WN 700 2-stop Boeing 737 MAX 8 (7M8) 9:15 Effective 2025-10-05 through 2025-10-26
Mon,Thu,Fri 16:25 Houston Hobby (HOU) 23:15 Midway, Chicago (MDW)
Southwest Airlines WN 1558 2-stop Boeing 737-700 (Scimitar Winglets) 6:50 Effective 2025-10-02 through 2025-10-31
Sat 07:55 Houston Hobby (HOU) 14:25 Midway, Chicago (MDW)
Southwest Airlines WN 1907 2-stop Boeing 737-700 (Scimitar Winglets) 6:30 Effective 2025-11-22 through 2025-11-29
Sat 07:55 Houston Hobby (HOU) 14:25 Midway, Chicago (MDW)
Southwest Airlines WN 1907 2-stop Boeing 737-700 (Scimitar Winglets) 6:30 Effective 2025-12-20 through 2026-01-03
Mon,Thu,Fri 10:05 Houston Hobby (HOU) 15:30 Midway, Chicago (MDW)
Southwest Airlines WN 1921 2-stop Boeing 737-700 (Scimitar Winglets) 5:25 Effective 2025-10-02 through 2025-10-31
Mon,Thu,Fri 06:05 Houston Hobby (HOU) 13:10 Midway, Chicago (MDW)
Southwest Airlines WN 2133 2-stop Boeing 737-700 (Scimitar Winglets) 7:05 Effective 2025-10-02 through 2025-10-31
Sun 11:15 Houston Hobby (HOU) 18:20 Midway, Chicago (MDW)
Southwest Airlines WN 3067 2-stop Boeing 737-700 (Scimitar Winglets) 7:05 Effective 2025-10-05 through 2025-10-26
Tue,Wed 11:05 Houston Hobby (HOU) 16:50 Midway, Chicago (MDW)
Southwest Airlines WN 3380 2-stop Boeing 737-700 (Scimitar Winglets) 5:45 Effective 2025-11-04 through 2025-11-12
Mon-Thu 11:05 Houston Hobby (HOU) 16:50 Midway, Chicago (MDW)
Southwest Airlines WN 3380 2-stop Boeing 737-700 (Scimitar Winglets) 5:45 Effective 2025-11-17 through 2025-11-20
Mon-Fri 11:05 Houston Hobby (HOU) 16:50 Midway, Chicago (MDW)
Southwest Airlines WN 3380 2-stop Boeing 737-700 (Scimitar Winglets) 5:45 Effective 2025-12-02 through 2025-12-11
Mon-Wed 11:05 Houston Hobby (HOU) 16:50 Midway, Chicago (MDW)
Southwest Airlines WN 3380 2-stop Boeing 737-700 (Scimitar Winglets) 5:45 Effective 2025-12-15 through 2025-12-17
Wed,Thu 11:05 Houston Hobby (HOU) 16:50 Midway, Chicago (MDW)
Southwest Airlines WN 3380 2-stop Boeing 737-700 (Scimitar Winglets) 5:45 Effective 2025-12-24 through 2026-01-01
Mon,Thu,Fri 08:00 Houston Hobby (HOU) 15:15 Midway, Chicago (MDW)
Southwest Airlines WN 3698 2-stop Boeing 737-700 (73W) 7:15 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 08:00 Houston Hobby (HOU) 15:15 Midway, Chicago (MDW)
Southwest Airlines WN 3698 2-stop Boeing 737-700 (73W) 7:15 Effective 2025-07-07 through 2025-08-04
Sun 08:15 Houston Hobby (HOU) 16:30 Midway, Chicago (MDW)
Southwest Airlines WN 154 3-stop Boeing 737-700 (73W) 8:15 Effective 2025-06-08 through 2025-08-03
Tue,Wed 11:25 Houston Hobby (HOU) 19:55 Midway, Chicago (MDW)
Southwest Airlines WN 3041 3-stop Boeing 737-700 (73W) 8:30 Effective 2025-06-10 through 2025-07-30
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All airlines flying from Houston Hobby (HOU) to Midway, Chicago (MDW).
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Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:

Effective 2025-10-05 through 2025-10-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:25, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:25, 1-stop
Boeing 737-700 (73W)

Effective 2025-08-05 through 2025-10-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:00, 1-stop
Boeing 737-800 (73H)

Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Effective 2025-06-07 through 2025-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Effective 2025-11-04 through 2025-11-12
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:30, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-17 through 2025-11-20
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 5:30, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-02 through 2025-12-11
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 5:30, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-15 through 2025-12-17
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:30, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-24 through 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 5:30, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-05 through 2025-10-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 9:15, 2-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-10-02 through 2025-10-31
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 6:50, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:30, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:30, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-02 through 2025-10-31
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:25, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-02 through 2025-10-31
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 7:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

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

Effective 2025-11-04 through 2025-11-12
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-17 through 2025-11-20
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 5:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-02 through 2025-12-11
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 5:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-15 through 2025-12-17
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-24 through 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 5:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 7:15, 2-stop
Boeing 737-700 (73W)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 7:15, 2-stop
Boeing 737-700 (73W)

Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 8:15, 3-stop
Boeing 737-700 (73W)

Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 8:30, 3-stop
Boeing 737-700 (73W)
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  • A domestic route departing from the Houston Hobby airport (HOU) and arriving at Midway, Chicago airport (MDW).
  • The flight distance is 937 miles, or 1509 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 2:20 and 2:35.