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

FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 15:10 Houston Hobby (HOU) 17:30 Chicago Midway (MDW) Southwest Airlines WN 3433 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-03-05 through 2026-04-06
Mon,Thu,Fri 05:05 Houston Hobby (HOU) 07:25 Chicago Midway (MDW) Southwest Airlines WN 3490 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-03-05 through 2026-04-06
Sat 15:30 Houston Hobby (HOU) 17:55 Chicago Midway (MDW) Southwest Airlines WN 3653 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-14 through 2026-02-28
Mon,Thu,Fri 05:10 Houston Hobby (HOU) 07:35 Chicago Midway (MDW) Southwest Airlines WN 3755 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-04-09 through 2026-06-01
Sun 05:00 Houston Hobby (HOU) 07:25 Chicago Midway (MDW) Southwest Airlines WN 3907 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-12 through 2026-05-17
Sun 05:00 Houston Hobby (HOU) 07:25 Chicago Midway (MDW) Southwest Airlines WN 3907 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-05-31
Sun 07:25 Houston Hobby (HOU) 09:50 Chicago Midway (MDW) Southwest Airlines WN 3907 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2026-05-24
Sat 21:05 Houston Hobby (HOU) 23:30 Chicago Midway (MDW) Southwest Airlines WN 4189 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-14 through 2026-02-28
Sat 20:20 Houston Hobby (HOU) 22:45 Chicago Midway (MDW) Southwest Airlines WN 4519 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-01-03
Tue,Wed 07:10 Houston Hobby (HOU) 09:35 Chicago Midway (MDW) Southwest Airlines WN 4520 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 19:00 Houston Hobby (HOU) 21:20 Chicago Midway (MDW) Southwest Airlines WN 4621 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-03-09 through 2026-04-06
Sun 12:20 Houston Hobby (HOU) 14:40 Chicago Midway (MDW) Southwest Airlines WN 4642 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 12:25 Houston Hobby (HOU) 14:45 Chicago Midway (MDW) Southwest Airlines WN 4642 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-03-05 through 2026-04-06
Thu,Fri,Sun 05:00 Houston Hobby (HOU) 07:25 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-11 through 2026-01-16
Sun 05:00 Houston Hobby (HOU) 07:25 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2026-02-01
Mon,Sun 05:05 Houston Hobby (HOU) 07:30 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-19 through 2026-01-25
Sat 05:55 Houston Hobby (HOU) 08:20 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-02-14 through 2026-02-28
Mon,Fri 06:20 Houston Hobby (HOU) 08:40 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-13 through 2026-02-20
Thu,Fri,Sun 06:20 Houston Hobby (HOU) 08:40 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-22 through 2026-03-01
Mon,Thu,Fri 06:30 Houston Hobby (HOU) 08:50 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-02-05 through 2026-02-09
Tue,Thu,Sun 06:30 Houston Hobby (HOU) 08:50 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-02-15 through 2026-02-19
Mon 06:30 Houston Hobby (HOU) 08:50 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:20 Operates only on 2026-02-23
Mon 06:30 Houston Hobby (HOU) 08:50 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-03-02
Mon-Fri 06:40 Houston Hobby (HOU) 09:05 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 06:40 Houston Hobby (HOU) 09:05 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-18 through 2026-01-23
Mon-Fri 06:40 Houston Hobby (HOU) 09:05 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 06:40 Houston Hobby (HOU) 09:05 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-08 through 2026-02-11
Wed 06:40 Houston Hobby (HOU) 09:05 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-02-18
Tue,Wed 06:40 Houston Hobby (HOU) 09:05 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-24 through 2026-03-04
Sat 07:00 Houston Hobby (HOU) 09:25 Chicago Midway (MDW) Southwest Airlines WN 4707 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-01-10 through 2026-02-07
Sun 19:10 Houston Hobby (HOU) 21:35 Chicago Midway (MDW) Southwest Airlines WN 4944 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-06-07 through 2026-08-02
Non-Direct Flights:
Sat 08:10 Houston Hobby (HOU) 12:15 Chicago Midway (MDW) Southwest Airlines WN 8 1-stop Boeing 737-800 (73H) 4:05 Effective 2026-06-06 through 2026-08-01
Sat 13:05 Houston Hobby (HOU) 17:10 Chicago Midway (MDW) Southwest Airlines WN 17 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-02-14 through 2026-02-28
Mon,Thu,Fri 13:30 Houston Hobby (HOU) 17:35 Chicago Midway (MDW) Southwest Airlines WN 30 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-04-09 through 2026-06-01
Mon,Thu,Fri 15:00 Houston Hobby (HOU) 19:05 Chicago Midway (MDW) Southwest Airlines WN 36 1-stop Boeing 737-800 (73H) 4:05 Effective 2026-06-04 through 2026-08-03
Sat 20:55 Houston Hobby (HOU) 00:50 Chicago Midway (MDW) Southwest Airlines WN 54 1-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-03-07 through 2026-04-04 The flight arrives 1 day after departure.
Mon,Thu,Fri 16:25 Houston Hobby (HOU) 20:25 Chicago Midway (MDW) Southwest Airlines WN 300 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-04-09 through 2026-06-01
Sun 13:30 Houston Hobby (HOU) 17:40 Chicago Midway (MDW) Southwest Airlines WN 425 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-06-07 through 2026-08-02
Sun 13:50 Houston Hobby (HOU) 18:00 Chicago Midway (MDW) Southwest Airlines WN 478 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-06-07 through 2026-08-02
Sun 13:35 Houston Hobby (HOU) 17:15 Chicago Midway (MDW) Southwest Airlines WN 492 1-stop Boeing 737-700 (Scimitar Winglets) 3:40 Operates only on 2026-05-24
Sat 12:15 Houston Hobby (HOU) 17:45 Chicago Midway (MDW) Southwest Airlines WN 823 1-stop Boeing 737-800 (73H) 5:30 Effective 2026-06-06 through 2026-08-01
Sun 13:00 Houston Hobby (HOU) 17:05 Chicago Midway (MDW) Southwest Airlines WN 864 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-03-08 through 2026-04-05
Mon,Tue,Fri,Sun 09:50 Houston Hobby (HOU) 14:05 Chicago Midway (MDW) Southwest Airlines WN 878 1-stop Boeing 737 MAX 8 (7M8) 4:15 Valid until 2026-01-04
Sat 08:15 Houston Hobby (HOU) 12:15 Chicago Midway (MDW) Southwest Airlines WN 1037 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 16:55 Houston Hobby (HOU) 20:55 Chicago Midway (MDW) Southwest Airlines WN 1096 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 16:55 Houston Hobby (HOU) 20:55 Chicago Midway (MDW) Southwest Airlines WN 1096 1-stop Boeing 737-700 (Scimitar Winglets) 4:00 Effective 2026-02-20 through 2026-03-01
Sat 13:40 Houston Hobby (HOU) 18:05 Chicago Midway (MDW) Southwest Airlines WN 1147 1-stop Boeing 737-700 (Scimitar Winglets) 4:25 Effective 2026-06-06 through 2026-08-01
Sun 14:55 Houston Hobby (HOU) 19:25 Chicago Midway (MDW) Southwest Airlines WN 1204 1-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2026-03-08 through 2026-04-05
Sun 17:15 Houston Hobby (HOU) 21:50 Chicago Midway (MDW) Southwest Airlines WN 1223 1-stop Boeing 737-700 (Scimitar Winglets) 4:35 Effective 2026-06-07 through 2026-08-02
Sat 16:35 Houston Hobby (HOU) 21:50 Chicago Midway (MDW) Southwest Airlines WN 1270 1-stop Boeing 737-700 (Scimitar Winglets) 5:15 Operates only on 2026-01-03

1 2 3 4 5

A domestic route departing from the Houston Hobby airport (HOU) and arriving at Chicago Midway 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.

Return (MDW-HOU) flights

Feedback - Disclaimer - Privacy

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN3433

15:10

Houston Hobby (HOU)

17:30

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3490

05:05

Houston Hobby (HOU)

07:25

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3653

15:30

Houston Hobby (HOU)

17:55

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3755

05:10

Houston Hobby (HOU)

07:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3907

05:00

Houston Hobby (HOU)

07:25

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3907

05:00

Houston Hobby (HOU)

07:25

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3907

07:25

Houston Hobby (HOU)

09:50

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4189

21:05

Houston Hobby (HOU)

23:30

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4519

20:20

Houston Hobby (HOU)

22:45

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4520

07:10

Houston Hobby (HOU)

09:35

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4621

19:00

Houston Hobby (HOU)

21:20

Chicago Midway (MDW)

Effective 2026-03-09 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4642

12:20

Houston Hobby (HOU)

14:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4642

12:25

Houston Hobby (HOU)

14:45

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4707

05:00

Houston Hobby (HOU)

07:25

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

05:00

Houston Hobby (HOU)

07:25

Chicago Midway (MDW)

Operates only on 2026-02-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

05:05

Houston Hobby (HOU)

07:30

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

05:55

Houston Hobby (HOU)

08:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4707

06:20

Houston Hobby (HOU)

08:40

Chicago Midway (MDW)

Effective 2026-02-13 through 2026-02-20

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4707

06:20

Houston Hobby (HOU)

08:40

Chicago Midway (MDW)

Effective 2026-02-22 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4707

06:30

Houston Hobby (HOU)

08:50

Chicago Midway (MDW)

Effective 2026-02-05 through 2026-02-09

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

06:30

Houston Hobby (HOU)

08:50

Chicago Midway (MDW)

Effective 2026-02-15 through 2026-02-19

Mon
-

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

06:30

Houston Hobby (HOU)

08:50

Chicago Midway (MDW)

Operates only on 2026-02-23

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

06:30

Houston Hobby (HOU)

08:50

Chicago Midway (MDW)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4707

06:40

Houston Hobby (HOU)

09:05

Chicago Midway (MDW)

Effective 2026-01-06 through 2026-01-14

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

06:40

Houston Hobby (HOU)

09:05

Chicago Midway (MDW)

Effective 2026-01-18 through 2026-01-23

Mon
-

Tue

Wed

Thu

Fri

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

06:40

Houston Hobby (HOU)

09:05

Chicago Midway (MDW)

Effective 2026-01-26 through 2026-02-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

06:40

Houston Hobby (HOU)

09:05

Chicago Midway (MDW)

Effective 2026-02-08 through 2026-02-11

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

06:40

Houston Hobby (HOU)

09:05

Chicago Midway (MDW)

Operates only on 2026-02-18

Mon
-

Tue
-

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4707

06:40

Houston Hobby (HOU)

09:05

Chicago Midway (MDW)

Effective 2026-02-24 through 2026-03-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4707

07:00

Houston Hobby (HOU)

09:25

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4944

19:10

Houston Hobby (HOU)

21:35

Chicago Midway (MDW)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN8

08:10

Houston Hobby (HOU)

12:15

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:05, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN17

13:05

Houston Hobby (HOU)

17:10

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN30

13:30

Houston Hobby (HOU)

17:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN36

15:00

Houston Hobby (HOU)

19:05

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:05, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN54

20:55

Houston Hobby (HOU)

00:50(+1)

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, 1-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Non-Direct Flights:

Southwest Airlines WN300

16:25

Houston Hobby (HOU)

20:25

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN425

13:30

Houston Hobby (HOU)

17:40

Chicago Midway (MDW)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN478

13:50

Houston Hobby (HOU)

18:00

Chicago Midway (MDW)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN492

13:35

Houston Hobby (HOU)

17:15

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN823

12:15

Houston Hobby (HOU)

17:45

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:30, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN864

13:00

Houston Hobby (HOU)

17:05

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN878

09:50

Houston Hobby (HOU)

14:05

Chicago Midway (MDW)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:15, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1037

08:15

Houston Hobby (HOU)

12:15

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1096

16:55

Houston Hobby (HOU)

20:55

Chicago Midway (MDW)

Effective 2026-02-12 through 2026-02-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1096

16:55

Houston Hobby (HOU)

20:55

Chicago Midway (MDW)

Effective 2026-02-20 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:00, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1147

13:40

Houston Hobby (HOU)

18:05

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:25, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1204

14:55

Houston Hobby (HOU)

19:25

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1223

17:15

Houston Hobby (HOU)

21:50

Chicago Midway (MDW)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1270

16:35

Houston Hobby (HOU)

21:50

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:15, 1-stop
Boeing 737-700 (Scimitar Winglets)

prev Page 4 / 5 next

A domestic route departing from the Houston Hobby airport (HOU) and arriving at Chicago Midway 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.

Return (MDW-HOU) flights

Feedback - Disclaimer - Privacy