All airlines flying from Houston Hobby (HOU) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Wed,Thu
14:35
Houston Hobby (HOU)
17:00
Chicago Midway (MDW) Southwest Airlines WN 2275 Non-stop Boeing 737-700 (73W) 2:25 Valid until 2026-01-01 |
| Mon
16:50
Houston Hobby (HOU)
19:15
Chicago Midway (MDW) Southwest Airlines WN 2275 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-01-05 |
| Sat
19:40
Houston Hobby (HOU)
22:00
Chicago Midway (MDW) Southwest Airlines WN 2278 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-08 through 2026-09-26 |
| Tue,Wed
20:50
Houston Hobby (HOU)
23:10
Chicago Midway (MDW) Southwest Airlines WN 2278 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-04 through 2026-09-30 |
| Sun
21:50
Houston Hobby (HOU)
00:10
Chicago Midway (MDW) Southwest Airlines WN 2278 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-09 through 2026-09-27 The flight arrives 1 day after departure. |
| Sat
13:20
Houston Hobby (HOU)
15:45
Chicago Midway (MDW) Southwest Airlines WN 2348 Non-stop Boeing 737-800 (73H) 2:25 Valid until 2026-01-03 |
| Mon,Tue,Fri,Sun
14:35
Houston Hobby (HOU)
17:00
Chicago Midway (MDW) Southwest Airlines WN 2348 Non-stop Boeing 737-800 (73H) 2:25 Valid until 2026-01-04 |
| Tue,Wed
14:25
Houston Hobby (HOU)
16:50
Chicago Midway (MDW) Southwest Airlines WN 2373 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-04-07 through 2026-06-03 |
| Mon,Thu,Fri
19:30
Houston Hobby (HOU)
21:55
Chicago Midway (MDW) Southwest Airlines WN 2373 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-04-09 through 2026-06-01 |
| Sat
20:20
Houston Hobby (HOU)
22:45
Chicago Midway (MDW) Southwest Airlines WN 2373 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-04-11 through 2026-05-30 |
| Sat
14:00
Houston Hobby (HOU)
16:20
Chicago Midway (MDW) Southwest Airlines WN 2463 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-01-10 through 2026-02-07 |
| Thu,Fri,Sun
14:45
Houston Hobby (HOU)
17:10
Chicago Midway (MDW) Southwest Airlines WN 2463 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
14:45
Houston Hobby (HOU)
17:10
Chicago Midway (MDW) Southwest Airlines WN 2463 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
14:45
Houston Hobby (HOU)
17:10
Chicago Midway (MDW) Southwest Airlines WN 2463 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
14:45
Houston Hobby (HOU)
17:10
Chicago Midway (MDW) Southwest Airlines WN 2463 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
14:45
Houston Hobby (HOU)
17:10
Chicago Midway (MDW) Southwest Airlines WN 2463 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-17 through 2026-02-23 |
| Mon
14:45
Houston Hobby (HOU)
17:10
Chicago Midway (MDW) Southwest Airlines WN 2463 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2026-03-02 |
| Mon,Thu,Fri
08:10
Houston Hobby (HOU)
10:35
Chicago Midway (MDW) Southwest Airlines WN 2649 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-03-05 through 2026-04-06 |
| Sun
08:15
Houston Hobby (HOU)
10:40
Chicago Midway (MDW) Southwest Airlines WN 2649 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-03-08 through 2026-04-05 |
| Tue,Wed
08:20
Houston Hobby (HOU)
10:45
Chicago Midway (MDW) Southwest Airlines WN 2649 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-03-10 through 2026-04-01 |
| Sat
09:35
Houston Hobby (HOU)
12:00
Chicago Midway (MDW) Southwest Airlines WN 2649 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-03-07 through 2026-04-04 |
| Sat
10:45
Houston Hobby (HOU)
13:10
Chicago Midway (MDW) Southwest Airlines WN 2733 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-14 through 2026-02-21 |
| Sat
10:50
Houston Hobby (HOU)
13:15
Chicago Midway (MDW) Southwest Airlines WN 2733 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-02-28 |
| Tue,Wed
11:10
Houston Hobby (HOU)
13:35
Chicago Midway (MDW) Southwest Airlines WN 2763 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-09 through 2026-07-29 |
| Mon,Thu,Fri
19:40
Houston Hobby (HOU)
22:00
Chicago Midway (MDW) Southwest Airlines WN 2771 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-06 through 2026-09-28 |
| Tue,Wed
08:15
Houston Hobby (HOU)
10:45
Chicago Midway (MDW) Southwest Airlines WN 2902 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-06-09 through 2026-07-29 |
| Sat
18:55
Houston Hobby (HOU)
21:20
Chicago Midway (MDW) Southwest Airlines WN 2916 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-14 through 2026-02-28 |
| Wed,Thu
06:35
Houston Hobby (HOU)
09:00
Chicago Midway (MDW) Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2026-01-01 |
| Sat
17:55
Houston Hobby (HOU)
20:20
Chicago Midway (MDW) Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2026-01-03 |
| Mon,Tue,Fri,Sun
18:50
Houston Hobby (HOU)
21:15
Chicago Midway (MDW) Southwest Airlines WN 2941 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2026-01-04 |
| Mon
19:25
Houston Hobby (HOU)
21:50
Chicago Midway (MDW) Southwest Airlines WN 2941 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2026-01-05 |
| Wed,Thu
19:45
Houston Hobby (HOU)
22:10
Chicago Midway (MDW) Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2026-01-01 |
| Mon
21:50
Houston Hobby (HOU)
00:10
Chicago Midway (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
Chicago Midway (MDW) Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Valid until 2026-01-03 The flight arrives 1 day after departure. |
| Mon,Tue,Fri,Sun
22:45
Houston Hobby (HOU)
01:10
Chicago Midway (MDW) Southwest Airlines WN 2942 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2026-01-04 The flight arrives 1 day after departure. |
| Sat
07:00
Houston Hobby (HOU)
09:25
Chicago Midway (MDW) Southwest Airlines WN 2963 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-11 through 2026-05-30 |
| Mon,Thu,Fri
08:10
Houston Hobby (HOU)
10:35
Chicago Midway (MDW) Southwest Airlines WN 2963 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-09 through 2026-06-01 |
| Sun
08:10
Houston Hobby (HOU)
10:35
Chicago Midway (MDW) Southwest Airlines WN 2963 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-04-12 through 2026-05-17 |
| Sun
08:10
Houston Hobby (HOU)
10:35
Chicago Midway (MDW) Southwest Airlines WN 2963 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-05-31 |
| Sun
09:35
Houston Hobby (HOU)
12:00
Chicago Midway (MDW) Southwest Airlines WN 2963 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-05-24 |
| Tue,Wed
20:40
Houston Hobby (HOU)
23:05
Chicago Midway (MDW) Southwest Airlines WN 2963 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-04-07 through 2026-06-03 |
| Sun
05:00
Houston Hobby (HOU)
07:20
Chicago Midway (MDW) Southwest Airlines WN 2968 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-03-08 through 2026-04-05 |
| Tue,Wed
06:15
Houston Hobby (HOU)
08:35
Chicago Midway (MDW) Southwest Airlines WN 2968 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-03-10 through 2026-04-01 |
| Sat
15:25
Houston Hobby (HOU)
17:50
Chicago Midway (MDW) Southwest Airlines WN 3395 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-04-11 through 2026-05-30 |
| Sun
15:25
Houston Hobby (HOU)
17:50
Chicago Midway (MDW) Southwest Airlines WN 3395 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-04-12 through 2026-05-17 |
| Sun
15:25
Houston Hobby (HOU)
17:50
Chicago Midway (MDW) Southwest Airlines WN 3395 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-05-31 |
| Sun
17:25
Houston Hobby (HOU)
19:50
Chicago Midway (MDW) Southwest Airlines WN 3395 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-05-24 |
| Tue,Wed
14:25
Houston Hobby (HOU)
16:45
Chicago Midway (MDW) Southwest Airlines WN 3433 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-03-10 through 2026-04-01 |
| Sun
14:50
Houston Hobby (HOU)
17:10
Chicago Midway (MDW) Southwest Airlines WN 3433 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-03-08 through 2026-04-05 |
| Sat
15:00
Houston Hobby (HOU)
17:20
Chicago Midway (MDW) Southwest Airlines WN 3433 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-03-07 through 2026-04-04 |
- 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.
