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

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FLIGHT SCHEDULE
Direct Flights:
Sun 10:30 Houston Hobby (HOU) 12:55 Midway, Chicago (MDW)
Southwest Airlines WN 7 Non-stop Boeing 737-700 (73W) 2:25 Operates only on 2025-05-25
Mon,Thu,Fri,Sun 11:50 Houston Hobby (HOU) 14:15 Midway, Chicago (MDW)
Southwest Airlines WN 15 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 11:50 Houston Hobby (HOU) 14:15 Midway, Chicago (MDW)
Southwest Airlines WN 15 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-11-21 through 2025-11-28
Fri,Sun 11:50 Houston Hobby (HOU) 14:15 Midway, Chicago (MDW)
Southwest Airlines WN 15 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-12-07 through 2025-12-14
Thu 11:50 Houston Hobby (HOU) 14:15 Midway, Chicago (MDW)
Southwest Airlines WN 15 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2025-12-18
Mon 11:50 Houston Hobby (HOU) 14:15 Midway, Chicago (MDW)
Southwest Airlines WN 15 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-01-05
Sun 21:20 Houston Hobby (HOU) 23:50 Midway, Chicago (MDW)
Southwest Airlines WN 27 Non-stop Boeing 737-700 (73W) 2:30 Effective 2025-06-08 through 2025-08-03
Thu 11:05 Houston Hobby (HOU) 13:30 Midway, Chicago (MDW)
Southwest Airlines WN 352 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2025-11-27
Sat 16:20 Houston Hobby (HOU) 18:45 Midway, Chicago (MDW)
Southwest Airlines WN 419 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-08-09 through 2025-09-27
Tue,Wed 16:45 Houston Hobby (HOU) 19:10 Midway, Chicago (MDW)
Southwest Airlines WN 419 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-08-05 through 2025-10-01
Mon,Thu,Fri 05:35 Houston Hobby (HOU) 08:00 Midway, Chicago (MDW)
Southwest Airlines WN 428 Non-stop Boeing 737-700 (73W) 2:25 Valid until 2025-06-02
Sat 06:05 Houston Hobby (HOU) 08:30 Midway, Chicago (MDW)
Southwest Airlines WN 428 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2025-05-31
Sun 06:55 Houston Hobby (HOU) 09:20 Midway, Chicago (MDW)
Southwest Airlines WN 428 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2025-05-18
Sun 06:55 Houston Hobby (HOU) 09:20 Midway, Chicago (MDW)
Southwest Airlines WN 428 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2025-06-01
Tue,Wed 07:15 Houston Hobby (HOU) 09:40 Midway, Chicago (MDW)
Southwest Airlines WN 428 Non-stop Boeing 737-700 (73W) 2:25 Valid until 2025-06-04
Sun 07:50 Houston Hobby (HOU) 10:15 Midway, Chicago (MDW)
Southwest Airlines WN 428 Non-stop Boeing 737-700 (73W) 2:25 Operates only on 2025-05-25
Mon,Thu,Fri 11:15 Houston Hobby (HOU) 13:40 Midway, Chicago (MDW)
Southwest Airlines WN 463 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-10-02 through 2025-10-31
Sat 17:55 Houston Hobby (HOU) 20:20 Midway, Chicago (MDW)
Southwest Airlines WN 463 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-10-04 through 2025-11-01
Tue,Wed 21:15 Houston Hobby (HOU) 23:35 Midway, Chicago (MDW)
Southwest Airlines WN 463 Non-stop Boeing 737-800 (73H) 2:20 Effective 2025-10-07 through 2025-10-29
Mon-Wed 08:25 Houston Hobby (HOU) 10:55 Midway, Chicago (MDW)
Southwest Airlines WN 569 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 08:25 Houston Hobby (HOU) 10:55 Midway, Chicago (MDW)
Southwest Airlines WN 569 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2025-12-19 through 2026-01-04
Sat 09:20 Houston Hobby (HOU) 11:55 Midway, Chicago (MDW)
Southwest Airlines WN 569 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-11-22 through 2025-11-29
Sat 09:20 Houston Hobby (HOU) 11:55 Midway, Chicago (MDW)
Southwest Airlines WN 569 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2025-12-20 through 2026-01-03
Sat 14:05 Houston Hobby (HOU) 16:30 Midway, Chicago (MDW)
Southwest Airlines WN 644 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-10-04 through 2025-11-01
Mon,Thu,Fri 14:50 Houston Hobby (HOU) 17:15 Midway, Chicago (MDW)
Southwest Airlines WN 644 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-10-02 through 2025-10-31
Sat 08:50 Houston Hobby (HOU) 11:20 Midway, Chicago (MDW)
Southwest Airlines WN 826 Non-stop Boeing 737-800 (73H) 2:30 Effective 2025-06-07 through 2025-06-28
Sat 08:50 Houston Hobby (HOU) 11:20 Midway, Chicago (MDW)
Southwest Airlines WN 826 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2025-07-05 through 2025-08-02
Sun 06:00 Houston Hobby (HOU) 08:25 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2025-11-30
Mon,Thu,Fri,Sun 06:15 Houston Hobby (HOU) 08:40 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-02 through 2025-11-16
Mon-Wed,Fri,Sun 06:15 Houston Hobby (HOU) 08:40 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-21 through 2025-11-28
Mon,Sun 06:15 Houston Hobby (HOU) 08:40 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-01 through 2025-12-07
Thu,Fri,Sun 06:15 Houston Hobby (HOU) 08:40 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-12 through 2025-12-21
Mon,Tue,Fri,Sun 06:15 Houston Hobby (HOU) 08:40 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-22 through 2026-01-05
Sat 06:30 Houston Hobby (HOU) 08:55 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-11-08 through 2025-11-15
Sat 06:30 Houston Hobby (HOU) 08:55 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-12-06 through 2025-12-13
Sat 06:40 Houston Hobby (HOU) 09:05 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-22 through 2025-11-29
Sat 06:40 Houston Hobby (HOU) 09:05 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-20 through 2026-01-03
Tue,Wed 10:20 Houston Hobby (HOU) 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-04 through 2025-11-12
Mon-Thu 10:20 Houston Hobby (HOU) 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-17 through 2025-11-20
Mon-Fri 10:20 Houston Hobby (HOU) 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-02 through 2025-12-11
Mon-Wed 10:20 Houston Hobby (HOU) 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-15 through 2025-12-17
Wed,Thu 10:20 Houston Hobby (HOU) 12:45 Midway, Chicago (MDW)
Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-24 through 2026-01-01
Sat 08:20 Houston Hobby (HOU) 10:45 Midway, Chicago (MDW)
Southwest Airlines WN 897 Non-stop Boeing 737-800 (73H) 2:25 Valid until 2025-05-31
Thu 14:10 Houston Hobby (HOU) 16:35 Midway, Chicago (MDW)
Southwest Airlines WN 1159 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2025-11-27
Sat 10:35 Houston Hobby (HOU) 13:00 Midway, Chicago (MDW)
Southwest Airlines WN 1334 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-11-08 through 2025-11-15
Sat 10:35 Houston Hobby (HOU) 13:00 Midway, Chicago (MDW)
Southwest Airlines WN 1334 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-12-06 through 2025-12-13
Sat 21:00 Houston Hobby (HOU) 23:30 Midway, Chicago (MDW)
Southwest Airlines WN 1375 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Valid until 2025-05-31
Sat 13:15 Houston Hobby (HOU) 15:45 Midway, Chicago (MDW)
Southwest Airlines WN 1592 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Valid until 2025-05-31
Sun 14:30 Houston Hobby (HOU) 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 1592 Non-stop Boeing 737-700 (73W) 2:30 Operates only on 2025-05-25
Sun 14:50 Houston Hobby (HOU) 17:20 Midway, Chicago (MDW)
Southwest Airlines WN 1592 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Valid until 2025-05-18
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All airlines flying from Houston Hobby (HOU) to Midway, Chicago (MDW).
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Select flight date:  Show Calendar
FLIGHT SCHEDULE
Direct Flights:

Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-700 (73W)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737-700 (73W)

Operates only on 2025-11-27
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)

Effective 2025-08-09 through 2025-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)

Effective 2025-08-05 through 2025-10-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (73W)

Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (73W)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (73W)

Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-700 (73W)

Effective 2025-10-02 through 2025-10-31
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)

Effective 2025-10-04 through 2025-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-10-07 through 2025-10-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-800 (73H)

Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-10-04 through 2025-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

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

Effective 2025-06-07 through 2025-06-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:30, non-stop
Boeing 737-800 (73H)

Effective 2025-07-05 through 2025-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-21 through 2025-11-28
Mon
Tue
Wed
Thu
-
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-01 through 2025-12-07
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-12 through 2025-12-21
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-22 through 2026-01-05
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)

Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-04 through 2025-11-12
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-17 through 2025-11-20
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-02 through 2025-12-11
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-15 through 2025-12-17
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-24 through 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)

Operates only on 2025-11-27
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Valid until 2025-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737-700 (73W)

Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)
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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 (plus 1h DST). Current time at both airports is 3:50am.
  • For direct flights, the flight time varies between 2:20 and 2:35.