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

FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 11:10 Chicago Midway (MDW) 13:55 Houston Hobby (HOU) Southwest Airlines WN 2818 Non-stop Boeing 737-700 (Scimitar Winglets) 2:45 Effective 2026-03-05 through 2026-04-06
Sat 12:30 Chicago Midway (MDW) 15:20 Houston Hobby (HOU) Southwest Airlines WN 2859 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-02-14 through 2026-02-28
Sat 13:45 Chicago Midway (MDW) 16:30 Houston Hobby (HOU) Southwest Airlines WN 2885 Non-stop Boeing 737-700 (Scimitar Winglets) 2:45 Operates only on 2026-01-03
Mon,Tue,Fri,Sun 14:50 Chicago Midway (MDW) 17:35 Houston Hobby (HOU) Southwest Airlines WN 2885 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Valid until 2026-01-04
Thu 06:55 Chicago Midway (MDW) 09:35 Houston Hobby (HOU) Southwest Airlines WN 2922 Non-stop Boeing 737-800 (73H) 2:40 Valid until 2026-01-01
Sat 11:50 Chicago Midway (MDW) 14:35 Houston Hobby (HOU) Southwest Airlines WN 2922 Non-stop Boeing 737-800 (73H) 2:45 Valid until 2026-01-03
Mon 19:00 Chicago Midway (MDW) 21:45 Houston Hobby (HOU) Southwest Airlines WN 2922 Non-stop Boeing 737-800 (73H) 2:45 Operates only on 2026-01-05
Mon,Tue,Fri,Sun 19:25 Chicago Midway (MDW) 22:10 Houston Hobby (HOU) Southwest Airlines WN 2922 Non-stop Boeing 737-800 (73H) 2:45 Valid until 2026-01-04
Sat 05:00 Chicago Midway (MDW) 07:40 Houston Hobby (HOU) Southwest Airlines WN 3102 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2026-04-11 through 2026-05-30
Tue,Wed 20:40 Chicago Midway (MDW) 23:20 Houston Hobby (HOU) Southwest Airlines WN 3151 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-04-07 through 2026-06-03
Sun 20:40 Chicago Midway (MDW) 23:20 Houston Hobby (HOU) Southwest Airlines WN 3151 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Operates only on 2026-05-24
Mon,Thu,Fri,Sun 21:40 Chicago Midway (MDW) 00:20 Houston Hobby (HOU) Southwest Airlines WN 3151 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-04-09 through 2026-05-22 The flight arrives 1 day after departure.
Mon,Thu,Fri,Sun 21:40 Chicago Midway (MDW) 00:20 Houston Hobby (HOU) Southwest Airlines WN 3151 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-05-25 through 2026-06-01 The flight arrives 1 day after departure.
Tue,Wed 14:10 Chicago Midway (MDW) 16:55 Houston Hobby (HOU) Southwest Airlines WN 3253 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 14:20 Chicago Midway (MDW) 17:05 Houston Hobby (HOU) Southwest Airlines WN 3253 Non-stop Boeing 737-800 (73H) 2:45 Effective 2026-03-05 through 2026-04-06
Sun 14:50 Chicago Midway (MDW) 17:40 Houston Hobby (HOU) Southwest Airlines WN 3253 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-03-08 through 2026-04-05
Sat 15:00 Chicago Midway (MDW) 17:50 Houston Hobby (HOU) Southwest Airlines WN 3253 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-03-07 through 2026-04-04
Sat 07:20 Chicago Midway (MDW) 09:50 Houston Hobby (HOU) Southwest Airlines WN 3295 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-08-08 through 2026-09-26
Sun 09:10 Chicago Midway (MDW) 11:40 Houston Hobby (HOU) Southwest Airlines WN 3295 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-08-09 through 2026-09-27
Sun 09:20 Chicago Midway (MDW) 12:00 Houston Hobby (HOU) Southwest Airlines WN 3414 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Operates only on 2026-05-24
Sun 10:10 Chicago Midway (MDW) 12:50 Houston Hobby (HOU) Southwest Airlines WN 3414 Non-stop Boeing 737-800 (73H) 2:40 Effective 2026-04-12 through 2026-05-17
Sun 10:10 Chicago Midway (MDW) 12:50 Houston Hobby (HOU) Southwest Airlines WN 3414 Non-stop Boeing 737-800 (73H) 2:40 Operates only on 2026-05-31
Mon-Fri 10:15 Chicago Midway (MDW) 13:00 Houston Hobby (HOU) Southwest Airlines WN 3414 Non-stop Boeing 737-700 (Scimitar Winglets) 2:45 Effective 2026-04-07 through 2026-06-03
Sun 07:20 Chicago Midway (MDW) 09:50 Houston Hobby (HOU) Southwest Airlines WN 3506 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-08-09 through 2026-09-27
Mon 08:00 Chicago Midway (MDW) 10:50 Houston Hobby (HOU) Southwest Airlines WN 3709 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2026-01-05
Mon,Tue,Fri,Sun 08:05 Chicago Midway (MDW) 10:55 Houston Hobby (HOU) Southwest Airlines WN 3709 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-04
Sat 08:10 Chicago Midway (MDW) 11:00 Houston Hobby (HOU) Southwest Airlines WN 3709 Non-stop Boeing 737-800 (73H) 2:50 Valid until 2026-01-03
Thu 20:35 Chicago Midway (MDW) 23:20 Houston Hobby (HOU) Southwest Airlines WN 3709 Non-stop Boeing 737-700 (73W) 2:45 Operates only on 2026-01-01
Sat 18:05 Chicago Midway (MDW) 20:50 Houston Hobby (HOU) Southwest Airlines WN 3946 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-04-11 through 2026-05-30
Mon,Thu,Fri 18:15 Chicago Midway (MDW) 20:55 Houston Hobby (HOU) Southwest Airlines WN 3946 Non-stop Boeing 737-800 (73H) 2:40 Effective 2026-04-09 through 2026-06-01
Sun 18:15 Chicago Midway (MDW) 20:55 Houston Hobby (HOU) Southwest Airlines WN 3946 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Effective 2026-04-12 through 2026-05-17
Sun 18:15 Chicago Midway (MDW) 20:55 Houston Hobby (HOU) Southwest Airlines WN 3946 Non-stop Boeing 737-700 (Scimitar Winglets) 2:40 Operates only on 2026-05-31
Tue 07:50 Chicago Midway (MDW) 10:25 Houston Hobby (HOU) Southwest Airlines WN 3950 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-08-04 through 2026-09-29
Sun 06:50 Chicago Midway (MDW) 09:30 Houston Hobby (HOU) Southwest Airlines WN 3964 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-04-12 through 2026-05-17
Sun 06:50 Chicago Midway (MDW) 09:30 Houston Hobby (HOU) Southwest Airlines WN 3964 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Operates only on 2026-05-31
Sun 07:30 Chicago Midway (MDW) 10:10 Houston Hobby (HOU) Southwest Airlines WN 3964 Non-stop Boeing 737-800 (73H) 2:40 Operates only on 2026-05-24
Sat 10:00 Chicago Midway (MDW) 12:40 Houston Hobby (HOU) Southwest Airlines WN 3964 Non-stop Boeing 737-800 (73H) 2:40 Effective 2026-04-11 through 2026-05-30
Mon,Thu,Fri 12:10 Chicago Midway (MDW) 14:50 Houston Hobby (HOU) Southwest Airlines WN 3964 Non-stop Boeing 737-800 (73H) 2:40 Effective 2026-04-09 through 2026-06-01
Tue,Wed 12:15 Chicago Midway (MDW) 14:55 Houston Hobby (HOU) Southwest Airlines WN 3964 Non-stop Boeing 737-800 (73H) 2:40 Effective 2026-04-07 through 2026-06-03
Wed 07:50 Chicago Midway (MDW) 10:25 Houston Hobby (HOU) Southwest Airlines WN 4047 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-08-05 through 2026-09-30
Thu,Fri,Sun 10:30 Chicago Midway (MDW) 13:20 Houston Hobby (HOU) Southwest Airlines WN 4050 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-01-11 through 2026-01-16
Mon,Sun 10:30 Chicago Midway (MDW) 13:20 Houston Hobby (HOU) Southwest Airlines WN 4050 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 10:30 Chicago Midway (MDW) 13:20 Houston Hobby (HOU) Southwest Airlines WN 4050 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-02-01 through 2026-02-06
Mon,Sun 10:30 Chicago Midway (MDW) 13:20 Houston Hobby (HOU) Southwest Airlines WN 4050 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 10:30 Chicago Midway (MDW) 13:20 Houston Hobby (HOU) Southwest Airlines WN 4050 Non-stop Boeing 737-800 (73H) 2:50 Effective 2026-02-17 through 2026-02-23
Mon 10:30 Chicago Midway (MDW) 13:20 Houston Hobby (HOU) Southwest Airlines WN 4050 Non-stop Boeing 737-800 (73H) 2:50 Operates only on 2026-03-02
Sat 11:15 Chicago Midway (MDW) 14:05 Houston Hobby (HOU) Southwest Airlines WN 4050 Non-stop Boeing 737-700 (Scimitar Winglets) 2:50 Effective 2026-01-10 through 2026-02-07
Mon,Thu,Fri 06:40 Chicago Midway (MDW) 09:15 Houston Hobby (HOU) Southwest Airlines WN 4497 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-06-04 through 2026-08-03
Tue,Wed 07:10 Chicago Midway (MDW) 09:45 Houston Hobby (HOU) Southwest Airlines WN 4497 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-06-09 through 2026-07-29
Sat 05:00 Chicago Midway (MDW) 08:00 Houston Hobby (HOU) Southwest Airlines WN 4547 Non-stop Boeing 737-800 (73H) 3:00 Effective 2026-02-14 through 2026-02-28

1 2 3 4 5

A domestic route departing from the Chicago Midway airport (MDW) and arriving at Houston Hobby airport (HOU).
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 2:25 and 3:00.

Return (HOU-MDW) flights

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN2818

11:10

Chicago Midway (MDW)

13:55

Houston Hobby (HOU)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2859

12:30

Chicago Midway (MDW)

15:20

Houston Hobby (HOU)

Effective 2026-02-14 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2885

13:45

Chicago Midway (MDW)

16:30

Houston Hobby (HOU)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2885

14:50

Chicago Midway (MDW)

17:35

Houston Hobby (HOU)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:45, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2922

06:55

Chicago Midway (MDW)

09:35

Houston Hobby (HOU)

Valid until 2026-01-01

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2922

11:50

Chicago Midway (MDW)

14:35

Houston Hobby (HOU)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:45, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2922

19:00

Chicago Midway (MDW)

21:45

Houston Hobby (HOU)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2922

19:25

Chicago Midway (MDW)

22:10

Houston Hobby (HOU)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:45, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3102

05:00

Chicago Midway (MDW)

07:40

Houston Hobby (HOU)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3151

20:40

Chicago Midway (MDW)

23:20

Houston Hobby (HOU)

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3151

20:40

Chicago Midway (MDW)

23:20

Houston Hobby (HOU)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3151

21:40

Chicago Midway (MDW)

00:20(+1)

Houston Hobby (HOU)

Effective 2026-04-09 through 2026-05-22

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3151

21:40

Chicago Midway (MDW)

00:20(+1)

Houston Hobby (HOU)

Effective 2026-05-25 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3253

14:10

Chicago Midway (MDW)

16:55

Houston Hobby (HOU)

Effective 2026-03-10 through 2026-04-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3253

14:20

Chicago Midway (MDW)

17:05

Houston Hobby (HOU)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3253

14:50

Chicago Midway (MDW)

17:40

Houston Hobby (HOU)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3253

15:00

Chicago Midway (MDW)

17:50

Houston Hobby (HOU)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3295

07:20

Chicago Midway (MDW)

09:50

Houston Hobby (HOU)

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3295

09:10

Chicago Midway (MDW)

11:40

Houston Hobby (HOU)

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3414

09:20

Chicago Midway (MDW)

12:00

Houston Hobby (HOU)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3414

10:10

Chicago Midway (MDW)

12:50

Houston Hobby (HOU)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3414

10:10

Chicago Midway (MDW)

12:50

Houston Hobby (HOU)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3414

10:15

Chicago Midway (MDW)

13:00

Houston Hobby (HOU)

Effective 2026-04-07 through 2026-06-03

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3506

07:20

Chicago Midway (MDW)

09:50

Houston Hobby (HOU)

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3709

08:00

Chicago Midway (MDW)

10:50

Houston Hobby (HOU)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3709

08:05

Chicago Midway (MDW)

10:55

Houston Hobby (HOU)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3709

08:10

Chicago Midway (MDW)

11:00

Houston Hobby (HOU)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3709

20:35

Chicago Midway (MDW)

23:20

Houston Hobby (HOU)

Operates only on 2026-01-01

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737-700 (73W)

Direct Flights:

Southwest Airlines WN3946

18:05

Chicago Midway (MDW)

20:50

Houston Hobby (HOU)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:45, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3946

18:15

Chicago Midway (MDW)

20:55

Houston Hobby (HOU)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3946

18:15

Chicago Midway (MDW)

20:55

Houston Hobby (HOU)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3946

18:15

Chicago Midway (MDW)

20:55

Houston Hobby (HOU)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3950

07:50

Chicago Midway (MDW)

10:25

Houston Hobby (HOU)

Effective 2026-08-04 through 2026-09-29

Mon
-

Tue

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3964

06:50

Chicago Midway (MDW)

09:30

Houston Hobby (HOU)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3964

06:50

Chicago Midway (MDW)

09:30

Houston Hobby (HOU)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3964

07:30

Chicago Midway (MDW)

10:10

Houston Hobby (HOU)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3964

10:00

Chicago Midway (MDW)

12:40

Houston Hobby (HOU)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3964

12:10

Chicago Midway (MDW)

14:50

Houston Hobby (HOU)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3964

12:15

Chicago Midway (MDW)

14:55

Houston Hobby (HOU)

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4047

07:50

Chicago Midway (MDW)

10:25

Houston Hobby (HOU)

Effective 2026-08-05 through 2026-09-30

Mon
-

Tue
-

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4050

10:30

Chicago Midway (MDW)

13:20

Houston Hobby (HOU)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4050

10:30

Chicago Midway (MDW)

13:20

Houston Hobby (HOU)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4050

10:30

Chicago Midway (MDW)

13:20

Houston Hobby (HOU)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4050

10:30

Chicago Midway (MDW)

13:20

Houston Hobby (HOU)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4050

10:30

Chicago Midway (MDW)

13:20

Houston Hobby (HOU)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4050

10:30

Chicago Midway (MDW)

13:20

Houston Hobby (HOU)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4050

11:15

Chicago Midway (MDW)

14:05

Houston Hobby (HOU)

Effective 2026-01-10 through 2026-02-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4497

06:40

Chicago Midway (MDW)

09:15

Houston Hobby (HOU)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4497

07:10

Chicago Midway (MDW)

09:45

Houston Hobby (HOU)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4547

05:00

Chicago Midway (MDW)

08:00

Houston Hobby (HOU)

Effective 2026-02-14 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:00, non-stop
Boeing 737-800 (73H)

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A domestic route departing from the Chicago Midway airport (MDW) and arriving at Houston Hobby airport (HOU).
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 2:25 and 3:00.

Return (HOU-MDW) flights

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