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

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Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Mon,Thu,Fri 08:00 Houston Hobby (HOU) 11:55 Midway, Chicago (MDW)
Southwest Airlines WN 8 1-stop Boeing 737-700 (73W) 3:55 Valid until 2025-06-02
Sat 08:00 Houston Hobby (HOU) 12:00 Midway, Chicago (MDW)
Southwest Airlines WN 8 1-stop Boeing 737 MAX 8 (7M8) 4:00 Valid until 2025-05-31
Sun 11:35 Houston Hobby (HOU) 16:45 Midway, Chicago (MDW)
Southwest Airlines WN 15 1-stop Boeing 737-700 (73W) 5:10 Effective 2025-08-10 through 2025-08-24
Sun 11:35 Houston Hobby (HOU) 16:45 Midway, Chicago (MDW)
Southwest Airlines WN 15 1-stop Boeing 737-700 (73W) 5:10 Effective 2025-09-07 through 2025-09-28
Tue,Wed 10:30 Houston Hobby (HOU) 14:30 Midway, Chicago (MDW)
Southwest Airlines WN 18 1-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-06-10 through 2025-07-30
Sun 14:35 Houston Hobby (HOU) 18:35 Midway, Chicago (MDW)
Southwest Airlines WN 34 1-stop Boeing 737 MAX 8 (7M8) 4:00 Operates only on 2025-05-25
Sat 15:05 Houston Hobby (HOU) 19:05 Midway, Chicago (MDW)
Southwest Airlines WN 36 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2025-11-08 through 2025-11-15
Sat 15:05 Houston Hobby (HOU) 19:05 Midway, Chicago (MDW)
Southwest Airlines WN 36 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2025-12-06 through 2025-12-13
Mon,Thu,Fri 15:55 Houston Hobby (HOU) 19:45 Midway, Chicago (MDW)
Southwest Airlines WN 172 1-stop Boeing 737-800 (73H) 3:50 Effective 2025-08-07 through 2025-09-29
Sun 12:25 Houston Hobby (HOU) 16:55 Midway, Chicago (MDW)
Southwest Airlines WN 483 1-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-06-08 through 2025-08-03
Mon,Thu,Fri 15:00 Houston Hobby (HOU) 19:20 Midway, Chicago (MDW)
Southwest Airlines WN 737 1-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 15:00 Houston Hobby (HOU) 19:20 Midway, Chicago (MDW)
Southwest Airlines WN 737 1-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-07-07 through 2025-08-04
Sun 10:20 Houston Hobby (HOU) 15:20 Midway, Chicago (MDW)
Southwest Airlines WN 813 1-stop Boeing 737-800 (73H) 5:00 Effective 2025-10-05 through 2025-10-26
Sat 15:20 Houston Hobby (HOU) 19:20 Midway, Chicago (MDW)
Southwest Airlines WN 867 1-stop Boeing 737-700 (73W) 4:00 Effective 2025-05-03 through 2025-05-10
Sat 15:20 Houston Hobby (HOU) 19:20 Midway, Chicago (MDW)
Southwest Airlines WN 867 1-stop Boeing 737-700 (73W) 4:00 Effective 2025-05-24 through 2025-05-31
Sun 09:05 Houston Hobby (HOU) 13:15 Midway, Chicago (MDW)
Southwest Airlines WN 875 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2025-10-05 through 2025-10-26
Mon-Wed 09:50 Houston Hobby (HOU) 14:05 Midway, Chicago (MDW)
Southwest Airlines WN 878 1-stop Boeing 737-800 (73H) 4:15 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 09:50 Houston Hobby (HOU) 14:05 Midway, Chicago (MDW)
Southwest Airlines WN 878 1-stop Boeing 737-800 (73H) 4:15 Effective 2025-12-19 through 2026-01-04
Sat 16:35 Houston Hobby (HOU) 21:50 Midway, Chicago (MDW)
Southwest Airlines WN 1270 1-stop Boeing 737-700 (Scimitar Winglets) 5:15 Effective 2025-11-22 through 2025-11-29
Sat 16:35 Houston Hobby (HOU) 21:50 Midway, Chicago (MDW)
Southwest Airlines WN 1270 1-stop Boeing 737-700 (Scimitar Winglets) 5:15 Effective 2025-12-20 through 2026-01-03
Mon,Thu,Fri 14:20 Houston Hobby (HOU) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 1500 1-stop Boeing 737-700 (73W) 5:10 Effective 2025-08-07 through 2025-09-29
Sat 13:35 Houston Hobby (HOU) 18:25 Midway, Chicago (MDW)
Southwest Airlines WN 1580 1-stop Boeing 737-700 (73W) 4:50 Valid until 2025-05-31
Thu 08:20 Houston Hobby (HOU) 12:40 Midway, Chicago (MDW)
Southwest Airlines WN 1721 1-stop Boeing 737-800 (73H) 4:20 Operates only on 2025-11-27
Tue,Wed 15:35 Houston Hobby (HOU) 19:35 Midway, Chicago (MDW)
Southwest Airlines WN 1763 1-stop Boeing 737-700 (73W) 4:00 Valid until 2025-06-04
Sat 12:25 Houston Hobby (HOU) 16:25 Midway, Chicago (MDW)
Southwest Airlines WN 1838 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2025-11-22 through 2025-11-29
Sat 12:25 Houston Hobby (HOU) 16:25 Midway, Chicago (MDW)
Southwest Airlines WN 1838 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2025-12-20 through 2026-01-03
Mon,Thu,Fri,Sun 13:30 Houston Hobby (HOU) 17:45 Midway, Chicago (MDW)
Southwest Airlines WN 2034 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 13:30 Houston Hobby (HOU) 17:45 Midway, Chicago (MDW)
Southwest Airlines WN 2034 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Effective 2025-11-21 through 2025-11-28
Fri,Sun 13:30 Houston Hobby (HOU) 17:45 Midway, Chicago (MDW)
Southwest Airlines WN 2034 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Effective 2025-12-07 through 2025-12-14
Thu 13:30 Houston Hobby (HOU) 17:45 Midway, Chicago (MDW)
Southwest Airlines WN 2034 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Operates only on 2025-12-18
Mon 13:30 Houston Hobby (HOU) 17:45 Midway, Chicago (MDW)
Southwest Airlines WN 2034 1-stop Boeing 737-700 (Scimitar Winglets) 4:15 Operates only on 2026-01-05
Sun 14:30 Houston Hobby (HOU) 19:45 Midway, Chicago (MDW)
Southwest Airlines WN 2082 1-stop Boeing 737-700 (Scimitar Winglets) 5:15 Operates only on 2025-11-30
Sun 16:45 Houston Hobby (HOU) 21:55 Midway, Chicago (MDW)
Southwest Airlines WN 2144 1-stop Boeing 737-700 (73W) 5:10 Valid until 2025-05-18
Sun 16:45 Houston Hobby (HOU) 21:55 Midway, Chicago (MDW)
Southwest Airlines WN 2144 1-stop Boeing 737-700 (73W) 5:10 Operates only on 2025-06-01
Tue,Wed 13:00 Houston Hobby (HOU) 17:15 Midway, Chicago (MDW)
Southwest Airlines WN 2170 1-stop Boeing 737-700 (73W) 4:15 Effective 2025-08-05 through 2025-10-01
Sun 17:25 Houston Hobby (HOU) 21:55 Midway, Chicago (MDW)
Southwest Airlines WN 2200 1-stop Boeing 737-700 (73W) 4:30 Valid until 2025-05-18
Sun 17:25 Houston Hobby (HOU) 21:55 Midway, Chicago (MDW)
Southwest Airlines WN 2200 1-stop Boeing 737-700 (73W) 4:30 Operates only on 2025-06-01
Sun 12:35 Houston Hobby (HOU) 17:05 Midway, Chicago (MDW)
Southwest Airlines WN 2317 1-stop Boeing 737 MAX 8 (7M8) 4:30 Valid until 2025-05-18
Sun 12:35 Houston Hobby (HOU) 17:05 Midway, Chicago (MDW)
Southwest Airlines WN 2317 1-stop Boeing 737 MAX 8 (7M8) 4:30 Operates only on 2025-06-01
Sat 10:55 Houston Hobby (HOU) 15:15 Midway, Chicago (MDW)
Southwest Airlines WN 2549 1-stop Boeing 737 MAX 8 (7M8) 4:20 Valid until 2025-05-31
Sat 15:20 Houston Hobby (HOU) 19:20 Midway, Chicago (MDW)
Southwest Airlines WN 2607 1-stop Boeing 737-800 (73H) 4:00 Effective 2025-11-22 through 2025-11-29
Sat 15:20 Houston Hobby (HOU) 19:20 Midway, Chicago (MDW)
Southwest Airlines WN 2607 1-stop Boeing 737-800 (73H) 4:00 Effective 2025-12-20 through 2026-01-03
Mon-Wed 17:25 Houston Hobby (HOU) 21:20 Midway, Chicago (MDW)
Southwest Airlines WN 2607 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 17:25 Houston Hobby (HOU) 21:20 Midway, Chicago (MDW)
Southwest Airlines WN 2607 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-12-19 through 2026-01-04
Sat 07:50 Houston Hobby (HOU) 11:45 Midway, Chicago (MDW)
Southwest Airlines WN 2923 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-11-22 through 2025-11-29
Sat 07:50 Houston Hobby (HOU) 11:45 Midway, Chicago (MDW)
Southwest Airlines WN 2923 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-12-20 through 2026-01-03
Sat 14:20 Houston Hobby (HOU) 19:30 Midway, Chicago (MDW)
Southwest Airlines WN 3053 1-stop Boeing 737 MAX 8 (7M8) 5:10 Valid until 2025-05-31
Tue,Wed 12:40 Houston Hobby (HOU) 17:15 Midway, Chicago (MDW)
Southwest Airlines WN 3146 1-stop Boeing 737-700 (73W) 4:35 Valid until 2025-06-04
Sat 13:05 Houston Hobby (HOU) 17:50 Midway, Chicago (MDW)
Southwest Airlines WN 3146 1-stop Boeing 737 MAX 8 (7M8) 4:45 Valid until 2025-05-31
Sat 08:35 Houston Hobby (HOU) 12:55 Midway, Chicago (MDW)
Southwest Airlines WN 3417 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-10-04 through 2025-11-01
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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:

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (73W)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Effective 2025-06-10 through 2025-07-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:00, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:00, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-08-07 through 2025-09-29
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:50, 1-stop
Boeing 737-800 (73H)

Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:30, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-06-05 through 2025-07-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:20, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-07-07 through 2025-08-04
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:20, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-10-05 through 2025-10-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:00, 1-stop
Boeing 737-800 (73H)

Effective 2025-05-03 through 2025-05-10
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, 1-stop
Boeing 737-700 (73W)

Effective 2025-05-24 through 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, 1-stop
Boeing 737-700 (73W)

Effective 2025-10-05 through 2025-10-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:15, 1-stop
Boeing 737-800 (73H)

Effective 2025-12-19 through 2026-01-04
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: 5:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-08-07 through 2025-09-29
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:50, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-11-27
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 4:20, 1-stop
Boeing 737-800 (73H)

Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:00, 1-stop
Boeing 737-700 (73W)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 4:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

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)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:10, 1-stop
Boeing 737-700 (73W)

Effective 2025-08-05 through 2025-10-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:15, 1-stop
Boeing 737-700 (73W)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:30, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:30, 1-stop
Boeing 737-700 (73W)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:30, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:30, 1-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, 1-stop
Boeing 737-800 (73H)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, 1-stop
Boeing 737-800 (73H)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:10, 1-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:35, 1-stop
Boeing 737-700 (73W)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:45, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-10-04 through 2025-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)
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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.