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

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Select flight date:  Show Calendar
FLIGHT SCHEDULE
Direct Flights:
Sun 05:35 Houston Hobby (HOU) 08:00 Midway, Chicago (MDW)
Southwest Airlines WN 2420 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-06-08 through 2025-08-03
Tue,Wed 15:00 Houston Hobby (HOU) 17:30 Midway, Chicago (MDW)
Southwest Airlines WN 2453 Non-stop Boeing 737-800 (73H) 2:30 Valid until 2025-06-04
Sun 17:45 Houston Hobby (HOU) 20:15 Midway, Chicago (MDW)
Southwest Airlines WN 2453 Non-stop Boeing 737-700 (73W) 2:30 Operates only on 2025-05-25
Mon,Thu,Fri 18:20 Houston Hobby (HOU) 20:45 Midway, Chicago (MDW)
Southwest Airlines WN 2453 Non-stop Boeing 737-700 (73W) 2:25 Valid until 2025-06-02
Sun 18:20 Houston Hobby (HOU) 20:45 Midway, Chicago (MDW)
Southwest Airlines WN 2453 Non-stop Boeing 737-800 (73H) 2:25 Valid until 2025-05-18
Sun 18:20 Houston Hobby (HOU) 20:45 Midway, Chicago (MDW)
Southwest Airlines WN 2453 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2025-06-01
Tue,Wed 06:35 Houston Hobby (HOU) 09:00 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-04 through 2025-11-12
Mon-Thu 06:35 Houston Hobby (HOU) 09:00 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-17 through 2025-11-20
Mon-Fri 06:35 Houston Hobby (HOU) 09:00 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-02 through 2025-12-11
Mon-Wed 06:35 Houston Hobby (HOU) 09:00 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-15 through 2025-12-17
Wed,Thu 06:35 Houston Hobby (HOU) 09:00 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-24 through 2026-01-01
Sat 17:55 Houston Hobby (HOU) 20:20 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-22 through 2025-11-29
Sat 17:55 Houston Hobby (HOU) 20:20 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-20 through 2026-01-03
Sat 18:10 Houston Hobby (HOU) 20:35 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-11-08 through 2025-11-15
Sat 18:10 Houston Hobby (HOU) 20:35 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-12-06 through 2025-12-13
Mon-Wed 18:50 Houston Hobby (HOU) 21:15 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 18:50 Houston Hobby (HOU) 21:15 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-19 through 2026-01-04
Mon,Thu,Fri,Sun 19:25 Houston Hobby (HOU) 21:50 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 19:25 Houston Hobby (HOU) 21:50 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-11-21 through 2025-11-28
Fri,Sun 19:25 Houston Hobby (HOU) 21:50 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-12-07 through 2025-12-14
Thu 19:25 Houston Hobby (HOU) 21:50 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2025-12-18
Mon 19:25 Houston Hobby (HOU) 21:50 Midway, Chicago (MDW)
Southwest Airlines WN 2941 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2026-01-05
Sat 14:00 Houston Hobby (HOU) 16:25 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-11-08 through 2025-11-15
Sat 14:00 Houston Hobby (HOU) 16:25 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-12-06 through 2025-12-13
Tue,Wed 19:45 Houston Hobby (HOU) 22:10 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-04 through 2025-11-12
Mon-Thu 19:45 Houston Hobby (HOU) 22:10 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-17 through 2025-11-20
Mon-Fri 19:45 Houston Hobby (HOU) 22:10 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-02 through 2025-12-11
Mon-Wed 19:45 Houston Hobby (HOU) 22:10 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-15 through 2025-12-17
Wed,Thu 19:45 Houston Hobby (HOU) 22:10 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-24 through 2026-01-01
Mon,Thu,Fri,Sun 21:50 Houston Hobby (HOU) 00:10 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2025-11-02 through 2025-11-16
The flight arrives 1 day after departure.
Mon,Fri,Sun 21:50 Houston Hobby (HOU) 00:10 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2025-11-21 through 2025-11-28
The flight arrives 1 day after departure.
Fri,Sun 21:50 Houston Hobby (HOU) 00:10 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2025-12-07 through 2025-12-14
The flight arrives 1 day after departure.
Thu 21:50 Houston Hobby (HOU) 00:10 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2025-12-18
The flight arrives 1 day after departure.
Mon 21:50 Houston Hobby (HOU) 00:10 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-01-05
The flight arrives 1 day after departure.
Sat 21:55 Houston Hobby (HOU) 00:15 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2025-11-22 through 2025-11-29
The flight arrives 1 day after departure.
Sat 21:55 Houston Hobby (HOU) 00:15 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2025-12-20 through 2026-01-03
The flight arrives 1 day after departure.
Sun 22:00 Houston Hobby (HOU) 00:20 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Operates only on 2025-11-30
The flight arrives 1 day after departure.
Mon-Wed 22:05 Houston Hobby (HOU) 00:25 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2025-11-25 through 2025-12-01
The flight arrives 1 day after departure.
Mon,Tue,Fri,Sun 22:05 Houston Hobby (HOU) 00:25 Midway, Chicago (MDW)
Southwest Airlines WN 2942 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2025-12-19 through 2026-01-04
The flight arrives 1 day after departure.
Sun 07:30 Houston Hobby (HOU) 10:00 Midway, Chicago (MDW)
Southwest Airlines WN 2952 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Operates only on 2025-08-31
Mon,Thu,Fri 07:35 Houston Hobby (HOU) 10:05 Midway, Chicago (MDW)
Southwest Airlines WN 2952 Non-stop Boeing 737-800 (73H) 2:30 Effective 2025-08-07 through 2025-09-29
Sun 08:35 Houston Hobby (HOU) 11:05 Midway, Chicago (MDW)
Southwest Airlines WN 2952 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2025-08-10 through 2025-08-24
Sun 08:35 Houston Hobby (HOU) 11:05 Midway, Chicago (MDW)
Southwest Airlines WN 2952 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2025-09-07 through 2025-09-28
Mon,Thu,Fri 12:10 Houston Hobby (HOU) 14:35 Midway, Chicago (MDW)
Southwest Airlines WN 2954 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-08-07 through 2025-09-29
Tue,Wed 13:25 Houston Hobby (HOU) 15:50 Midway, Chicago (MDW)
Southwest Airlines WN 2954 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-08-05 through 2025-10-01
Sat 13:35 Houston Hobby (HOU) 16:00 Midway, Chicago (MDW)
Southwest Airlines WN 2954 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-08-09 through 2025-09-27
Sun 14:20 Houston Hobby (HOU) 16:45 Midway, Chicago (MDW)
Southwest Airlines WN 2954 Non-stop Boeing 737-700 (73W) 2:25 Operates only on 2025-08-31
Sun 14:55 Houston Hobby (HOU) 17:20 Midway, Chicago (MDW)
Southwest Airlines WN 2954 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-08-10 through 2025-08-24
Sun 14:55 Houston Hobby (HOU) 17:20 Midway, Chicago (MDW)
Southwest Airlines WN 2954 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-09-07 through 2025-09-28
Sun 09:05 Houston Hobby (HOU) 11:30 Midway, Chicago (MDW)
Southwest Airlines WN 2962 Non-stop Boeing 737 MAX 8 (7M8) 2:25 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:
Southwest Airlines WN2420
05:35
Houston Hobby (HOU)

08:00
Midway, Chicago (MDW)
Effective 2025-06-08 through 2025-08-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN2453
15:00
Houston Hobby (HOU)

17:30
Midway, Chicago (MDW)
Valid until 2025-06-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:30, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2453
17:45
Houston Hobby (HOU)

20:15
Midway, Chicago (MDW)
Operates only on 2025-05-25
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737-700 (73W)
Southwest Airlines WN2453
18:20
Houston Hobby (HOU)

20:45
Midway, Chicago (MDW)
Valid until 2025-06-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (73W)
Southwest Airlines WN2453
18:20
Houston Hobby (HOU)

20:45
Midway, Chicago (MDW)
Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2453
18:20
Houston Hobby (HOU)

20:45
Midway, Chicago (MDW)
Operates only on 2025-06-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2941
06:35
Houston Hobby (HOU)

09:00
Midway, Chicago (MDW)
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)
Southwest Airlines WN2941
06:35
Houston Hobby (HOU)

09:00
Midway, Chicago (MDW)
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)
Southwest Airlines WN2941
06:35
Houston Hobby (HOU)

09:00
Midway, Chicago (MDW)
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)
Southwest Airlines WN2941
06:35
Houston Hobby (HOU)

09:00
Midway, Chicago (MDW)
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)
Southwest Airlines WN2941
06:35
Houston Hobby (HOU)

09:00
Midway, Chicago (MDW)
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)
Southwest Airlines WN2941
17:55
Houston Hobby (HOU)

20:20
Midway, Chicago (MDW)
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)
Southwest Airlines WN2941
17:55
Houston Hobby (HOU)

20:20
Midway, Chicago (MDW)
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)
Southwest Airlines WN2941
18:10
Houston Hobby (HOU)

20:35
Midway, Chicago (MDW)
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)
Southwest Airlines WN2941
18:10
Houston Hobby (HOU)

20:35
Midway, Chicago (MDW)
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)
Southwest Airlines WN2941
18:50
Houston Hobby (HOU)

21:15
Midway, Chicago (MDW)
Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN2941
18:50
Houston Hobby (HOU)

21:15
Midway, Chicago (MDW)
Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN2941
19:25
Houston Hobby (HOU)

21:50
Midway, Chicago (MDW)
Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2941
19:25
Houston Hobby (HOU)

21:50
Midway, Chicago (MDW)
Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2941
19:25
Houston Hobby (HOU)

21:50
Midway, Chicago (MDW)
Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2941
19:25
Houston Hobby (HOU)

21:50
Midway, Chicago (MDW)
Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2941
19:25
Houston Hobby (HOU)

21:50
Midway, Chicago (MDW)
Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2942
14:00
Houston Hobby (HOU)

16:25
Midway, Chicago (MDW)
Effective 2025-11-08 through 2025-11-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2942
14:00
Houston Hobby (HOU)

16:25
Midway, Chicago (MDW)
Effective 2025-12-06 through 2025-12-13
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2942
19:45
Houston Hobby (HOU)

22:10
Midway, Chicago (MDW)
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)
Southwest Airlines WN2942
19:45
Houston Hobby (HOU)

22:10
Midway, Chicago (MDW)
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)
Southwest Airlines WN2942
19:45
Houston Hobby (HOU)

22:10
Midway, Chicago (MDW)
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)
Southwest Airlines WN2942
19:45
Houston Hobby (HOU)

22:10
Midway, Chicago (MDW)
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)
Southwest Airlines WN2942
19:45
Houston Hobby (HOU)

22:10
Midway, Chicago (MDW)
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)
Southwest Airlines WN2942
21:50
Houston Hobby (HOU)

00:10(+1)
Midway, Chicago (MDW)
Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.
Southwest Airlines WN2942
21:50
Houston Hobby (HOU)

00:10(+1)
Midway, Chicago (MDW)
Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.
Southwest Airlines WN2942
21:50
Houston Hobby (HOU)

00:10(+1)
Midway, Chicago (MDW)
Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.
Southwest Airlines WN2942
21:50
Houston Hobby (HOU)

00:10(+1)
Midway, Chicago (MDW)
Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.
Southwest Airlines WN2942
21:50
Houston Hobby (HOU)

00:10(+1)
Midway, Chicago (MDW)
Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.
Southwest Airlines WN2942
21:55
Houston Hobby (HOU)

00:15(+1)
Midway, Chicago (MDW)
Effective 2025-11-22 through 2025-11-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.
Southwest Airlines WN2942
21:55
Houston Hobby (HOU)

00:15(+1)
Midway, Chicago (MDW)
Effective 2025-12-20 through 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.
Southwest Airlines WN2942
22:00
Houston Hobby (HOU)

00:20(+1)
Midway, Chicago (MDW)
Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.
Southwest Airlines WN2942
22:05
Houston Hobby (HOU)

00:25(+1)
Midway, Chicago (MDW)
Effective 2025-11-25 through 2025-12-01
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.
Southwest Airlines WN2942
22:05
Houston Hobby (HOU)

00:25(+1)
Midway, Chicago (MDW)
Effective 2025-12-19 through 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.
Southwest Airlines WN2952
07:30
Houston Hobby (HOU)

10:00
Midway, Chicago (MDW)
Operates only on 2025-08-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN2952
07:35
Houston Hobby (HOU)

10:05
Midway, Chicago (MDW)
Effective 2025-08-07 through 2025-09-29
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:30, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2952
08:35
Houston Hobby (HOU)

11:05
Midway, Chicago (MDW)
Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN2952
08:35
Houston Hobby (HOU)

11:05
Midway, Chicago (MDW)
Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN2954
12:10
Houston Hobby (HOU)

14:35
Midway, Chicago (MDW)
Effective 2025-08-07 through 2025-09-29
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN2954
13:25
Houston Hobby (HOU)

15:50
Midway, Chicago (MDW)
Effective 2025-08-05 through 2025-10-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)
Southwest Airlines WN2954
13:35
Houston Hobby (HOU)

16:00
Midway, Chicago (MDW)
Effective 2025-08-09 through 2025-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (73W)
Southwest Airlines WN2954
14:20
Houston Hobby (HOU)

16:45
Midway, Chicago (MDW)
Operates only on 2025-08-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-700 (73W)
Southwest Airlines WN2954
14:55
Houston Hobby (HOU)

17:20
Midway, Chicago (MDW)
Effective 2025-08-10 through 2025-08-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN2954
14:55
Houston Hobby (HOU)

17:20
Midway, Chicago (MDW)
Effective 2025-09-07 through 2025-09-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)
Southwest Airlines WN2962
09:05
Houston Hobby (HOU)

11:30
Midway, Chicago (MDW)
Valid until 2025-05-18
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, 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 11:42am.
  • For direct flights, the flight time varies between 2:20 and 2:35.
Return (MDW-HOU) flights
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