All airlines flying from Houston Hobby (HOU) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Mon
11:50
Houston Hobby (HOU)
14:15
Chicago Midway (MDW) Southwest Airlines WN 15 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-01-05 |
| Mon,Thu,Fri
18:00
Houston Hobby (HOU)
20:25
Chicago Midway (MDW) Southwest Airlines WN 39 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
18:00
Houston Hobby (HOU)
20:25
Chicago Midway (MDW) Southwest Airlines WN 39 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-20 through 2026-03-01 |
| Tue,Wed
18:20
Houston Hobby (HOU)
20:45
Chicago Midway (MDW) Southwest Airlines WN 41 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-06-09 through 2026-07-29 |
| Sat
18:45
Houston Hobby (HOU)
21:10
Chicago Midway (MDW) Southwest Airlines WN 41 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-06-06 through 2026-08-01 |
| Mon,Thu,Fri
15:20
Houston Hobby (HOU)
17:45
Chicago Midway (MDW) Southwest Airlines WN 123 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-04-09 through 2026-06-01 |
| Tue,Wed
18:10
Houston Hobby (HOU)
20:35
Chicago Midway (MDW) Southwest Airlines WN 123 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-07 through 2026-06-03 |
| Sun
05:45
Houston Hobby (HOU)
08:10
Chicago Midway (MDW) Southwest Airlines WN 149 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-08-09 through 2026-09-27 |
| Tue,Wed
06:50
Houston Hobby (HOU)
09:15
Chicago Midway (MDW) Southwest Airlines WN 149 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-04 through 2026-09-30 |
| Sat
07:15
Houston Hobby (HOU)
09:45
Chicago Midway (MDW) Southwest Airlines WN 149 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-08-08 through 2026-09-26 |
| Sun
18:50
Houston Hobby (HOU)
21:15
Chicago Midway (MDW) Southwest Airlines WN 222 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-04-12 through 2026-05-17 |
| Sun
18:50
Houston Hobby (HOU)
21:15
Chicago Midway (MDW) Southwest Airlines WN 222 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2026-05-31 |
| Mon,Thu,Fri
06:10
Houston Hobby (HOU)
08:35
Chicago Midway (MDW) Southwest Airlines WN 256 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-08-06 through 2026-09-28 |
| Sun
08:25
Houston Hobby (HOU)
10:55
Chicago Midway (MDW) Southwest Airlines WN 256 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-08-09 through 2026-09-27 |
| Tue,Wed
09:40
Houston Hobby (HOU)
12:15
Chicago Midway (MDW) Southwest Airlines WN 256 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-08-04 through 2026-09-30 |
| Sat
10:30
Houston Hobby (HOU)
13:00
Chicago Midway (MDW) Southwest Airlines WN 256 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-08-08 through 2026-09-26 |
| Mon,Thu,Fri
07:25
Houston Hobby (HOU)
09:50
Chicago Midway (MDW) Southwest Airlines WN 265 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-08-06 through 2026-09-28 |
| Tue
16:45
Houston Hobby (HOU)
19:10
Chicago Midway (MDW) Southwest Airlines WN 265 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-08-04 through 2026-09-29 |
| Sun
18:15
Houston Hobby (HOU)
20:40
Chicago Midway (MDW) Southwest Airlines WN 265 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-09 through 2026-09-27 |
| Sat
18:25
Houston Hobby (HOU)
20:45
Chicago Midway (MDW) Southwest Airlines WN 359 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-03-07 through 2026-04-04 |
| Tue,Wed
21:30
Houston Hobby (HOU)
23:55
Chicago Midway (MDW) Southwest Airlines WN 359 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-03-10 through 2026-04-01 |
| Sat
05:15
Houston Hobby (HOU)
07:35
Chicago Midway (MDW) Southwest Airlines WN 473 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-03-07 through 2026-04-04 |
| Mon,Tue,Fri,Sun
08:25
Houston Hobby (HOU)
10:55
Chicago Midway (MDW) Southwest Airlines WN 569 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Valid until 2026-01-04 |
| Sat
09:20
Houston Hobby (HOU)
11:55
Chicago Midway (MDW) Southwest Airlines WN 569 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Valid until 2026-01-03 |
| Sat
08:30
Houston Hobby (HOU)
10:55
Chicago Midway (MDW) Southwest Airlines WN 670 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-06-06 through 2026-08-01 |
| Mon,Tue,Fri,Sun
06:15
Houston Hobby (HOU)
08:40
Chicago Midway (MDW) Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2026-01-05 |
| Sat
06:40
Houston Hobby (HOU)
09:05
Chicago Midway (MDW) Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2026-01-03 |
| Wed,Thu
10:20
Houston Hobby (HOU)
12:45
Chicago Midway (MDW) Southwest Airlines WN 851 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2026-01-01 |
| Sun
07:20
Houston Hobby (HOU)
09:45
Chicago Midway (MDW) Southwest Airlines WN 993 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-07 through 2026-08-02 |
| Mon,Thu,Fri
08:10
Houston Hobby (HOU)
10:40
Chicago Midway (MDW) Southwest Airlines WN 1294 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-06-04 through 2026-08-03 |
| Mon-Fri
20:30
Houston Hobby (HOU)
22:55
Chicago Midway (MDW) Southwest Airlines WN 1325 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-06 through 2026-01-14 |
| Sun
20:30
Houston Hobby (HOU)
22:55
Chicago Midway (MDW) Southwest Airlines WN 1325 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-01-18 |
| Mon-Fri
20:30
Houston Hobby (HOU)
22:55
Chicago Midway (MDW) Southwest Airlines WN 1325 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-20 through 2026-02-04 |
| Tue,Wed,Sun
20:30
Houston Hobby (HOU)
22:55
Chicago Midway (MDW) Southwest Airlines WN 1325 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
20:30
Houston Hobby (HOU)
22:55
Chicago Midway (MDW) Southwest Airlines WN 1325 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-18 through 2026-03-04 |
| Mon,Thu,Fri
05:00
Houston Hobby (HOU)
07:25
Chicago Midway (MDW) Southwest Airlines WN 1372 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-06 through 2026-09-28 |
| Sun
05:10
Houston Hobby (HOU)
07:35
Chicago Midway (MDW) Southwest Airlines WN 1573 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-06-07 through 2026-08-02 |
| Tue,Wed
18:00
Houston Hobby (HOU)
20:25
Chicago Midway (MDW) Southwest Airlines WN 1575 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-03-10 through 2026-04-01 |
| Mon,Thu,Fri
20:25
Houston Hobby (HOU)
22:50
Chicago Midway (MDW) Southwest Airlines WN 1575 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-03-05 through 2026-04-06 |
| Sat
21:15
Houston Hobby (HOU)
23:40
Chicago Midway (MDW) Southwest Airlines WN 1575 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-03-07 through 2026-04-04 |
| Mon-Fri
14:15
Houston Hobby (HOU)
16:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
14:15
Houston Hobby (HOU)
16:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
14:15
Houston Hobby (HOU)
16:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-01-26 through 2026-02-04 |
| Sun
14:15
Houston Hobby (HOU)
16:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-02-08 |
| Tue,Wed
14:15
Houston Hobby (HOU)
16:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-10 through 2026-02-11 |
| Tue,Wed
14:15
Houston Hobby (HOU)
16:40
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-18 through 2026-03-04 |
| Sat
18:00
Houston Hobby (HOU)
20:25
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-10 through 2026-01-31 |
| Sat
18:00
Houston Hobby (HOU)
20:25
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-02-07 |
| Mon
19:40
Houston Hobby (HOU)
22:05
Chicago Midway (MDW) Southwest Airlines WN 1676 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-02-16 |
| 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 2026-01-11 |
- 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.
