All airlines flying from Houston Hobby (HOU) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Sun
20:00
Houston Hobby (HOU)
22:20
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Operates only on 2026-01-25 |
| Mon,Thu,Fri
20:15
Houston Hobby (HOU)
22:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-01-15 through 2026-01-19 |
| Thu,Fri,Sun
20:15
Houston Hobby (HOU)
22:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
20:15
Houston Hobby (HOU)
22:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
20:15
Houston Hobby (HOU)
22:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-17 through 2026-02-23 |
| Mon
20:15
Houston Hobby (HOU)
22:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-03-02 |
| Thu,Fri
20:45
Houston Hobby (HOU)
23:10
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-02-12 through 2026-02-13 |
| Thu,Fri,Sun
20:45
Houston Hobby (HOU)
23:10
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-02-20 through 2026-03-01 |
| Sun
19:10
Houston Hobby (HOU)
21:30
Chicago Midway (MDW) Southwest Airlines WN 1779 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-03-08 through 2026-04-05 |
| Sun
19:05
Houston Hobby (HOU)
21:30
Chicago Midway (MDW) Southwest Airlines WN 1798 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-05-24 |
| Mon-Fri
11:05
Houston Hobby (HOU)
13:30
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
11:05
Houston Hobby (HOU)
13:30
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
11:05
Houston Hobby (HOU)
13:30
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-26 through 2026-02-04 |
| Wed,Sun
11:05
Houston Hobby (HOU)
13:30
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-08 through 2026-02-11 |
| Tue
11:05
Houston Hobby (HOU)
13:30
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-02-10 |
| Tue,Wed
11:05
Houston Hobby (HOU)
13:30
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-18 through 2026-03-04 |
| Sat
11:25
Houston Hobby (HOU)
13:50
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-01-10 through 2026-02-07 |
| Thu,Fri,Sun
11:55
Houston Hobby (HOU)
14:20
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
11:55
Houston Hobby (HOU)
14:20
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
11:55
Houston Hobby (HOU)
14:20
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
11:55
Houston Hobby (HOU)
14:20
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
11:55
Houston Hobby (HOU)
14:20
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-17 through 2026-02-23 |
| Mon
11:55
Houston Hobby (HOU)
14:20
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2026-03-02 |
| Mon,Thu,Fri
12:10
Houston Hobby (HOU)
14:35
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
12:10
Houston Hobby (HOU)
14:35
Chicago Midway (MDW) Southwest Airlines WN 1910 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-02-20 through 2026-03-01 |
| Mon,Thu,Fri
14:20
Houston Hobby (HOU)
16:40
Chicago Midway (MDW) Southwest Airlines WN 1964 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-06 through 2026-09-28 |
| Wed
16:45
Houston Hobby (HOU)
19:10
Chicago Midway (MDW) Southwest Airlines WN 1964 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-08-05 through 2026-09-30 |
| Sun
14:40
Houston Hobby (HOU)
17:05
Chicago Midway (MDW) Southwest Airlines WN 1966 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-08-09 through 2026-09-27 |
| Tue,Wed
14:45
Houston Hobby (HOU)
17:10
Chicago Midway (MDW) Southwest Airlines WN 1966 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-04 through 2026-09-30 |
| Sat
15:15
Houston Hobby (HOU)
17:40
Chicago Midway (MDW) Southwest Airlines WN 1966 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-08-08 through 2026-09-26 |
| Mon,Thu,Fri
17:45
Houston Hobby (HOU)
20:10
Chicago Midway (MDW) Southwest Airlines WN 1966 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-06 through 2026-09-28 |
| Sun
12:00
Houston Hobby (HOU)
14:25
Chicago Midway (MDW) Southwest Airlines WN 1988 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-09 through 2026-09-27 |
| Tue,Wed
09:15
Houston Hobby (HOU)
11:40
Chicago Midway (MDW) Southwest Airlines WN 2002 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-07 through 2026-06-03 |
| Mon,Thu,Fri
12:30
Houston Hobby (HOU)
14:55
Chicago Midway (MDW) Southwest Airlines WN 2002 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-04-09 through 2026-06-01 |
| Sat,Sun
12:40
Houston Hobby (HOU)
15:05
Chicago Midway (MDW) Southwest Airlines WN 2002 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-11 through 2026-05-23 |
| Sat,Sun
12:40
Houston Hobby (HOU)
15:05
Chicago Midway (MDW) Southwest Airlines WN 2002 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-05-30 through 2026-05-31 |
| Sun
14:35
Houston Hobby (HOU)
17:05
Chicago Midway (MDW) Southwest Airlines WN 2002 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Operates only on 2026-05-24 |
| Mon,Thu-Sat
05:00
Houston Hobby (HOU)
07:25
Chicago Midway (MDW) Southwest Airlines WN 2038 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-04 through 2026-08-03 |
| Tue,Wed
05:25
Houston Hobby (HOU)
07:50
Chicago Midway (MDW) Southwest Airlines WN 2038 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-06-09 through 2026-07-29 |
| Mon,Thu,Fri
06:25
Houston Hobby (HOU)
08:50
Chicago Midway (MDW) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-04 through 2026-08-03 |
| Mon,Thu,Fri
13:30
Houston Hobby (HOU)
15:55
Chicago Midway (MDW) Southwest Airlines WN 2041 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-06-04 through 2026-08-03 |
| Sat
14:20
Houston Hobby (HOU)
16:45
Chicago Midway (MDW) Southwest Airlines WN 2041 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-06 through 2026-08-01 |
| Tue,Wed
14:35
Houston Hobby (HOU)
17:00
Chicago Midway (MDW) Southwest Airlines WN 2042 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-06-09 through 2026-07-29 |
| Sun
15:15
Houston Hobby (HOU)
17:40
Chicago Midway (MDW) Southwest Airlines WN 2042 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-07 through 2026-08-02 |
| Mon,Thu,Fri
16:40
Houston Hobby (HOU)
19:05
Chicago Midway (MDW) Southwest Airlines WN 2042 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-04 through 2026-08-03 |
| Mon,Thu,Fri
18:50
Houston Hobby (HOU)
21:15
Chicago Midway (MDW) Southwest Airlines WN 2043 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-06-04 through 2026-08-03 |
| Mon,Thu,Fri
20:35
Houston Hobby (HOU)
23:00
Chicago Midway (MDW) Southwest Airlines WN 2044 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-04 through 2026-08-03 |
| Sat
20:45
Houston Hobby (HOU)
23:10
Chicago Midway (MDW) Southwest Airlines WN 2044 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-06 through 2026-08-01 |
| Sun
21:20
Houston Hobby (HOU)
23:45
Chicago Midway (MDW) Southwest Airlines WN 2044 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-07 through 2026-08-02 |
| Tue,Wed
21:25
Houston Hobby (HOU)
23:50
Chicago Midway (MDW) Southwest Airlines WN 2044 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-09 through 2026-07-29 |
- 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.
