Direct flights from Houston Hobby to Chicago
38 nonstop flights a week on 1 airline. Zero layovers — one hop from HOU to MDW.
Flight time: about 2h9m nonstop
Which days does it fly?
When does it fly?
Departure times in Houston Hobby local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| Southwest SWA1444 | 5:04a | 2h | Thu |
| Southwest SWA1156 | 5:11a | 2h5m | Mon, Fri |
| Southwest SWA149 | 5:47a | 2h2m | Sun |
| Southwest SWA149 | 7:10a | 2h | Wed, Sat |
| Southwest SWA265 | 7:29a | 2h10m | Mon, Fri |
| Southwest SWA149 | 7:41a | 2h24m | Tue |
| Southwest SWA256 | 8:27a | 2h13m | Sun |
| Southwest SWA2085 | 9:08a | 1h57m | Thu |
| Southwest SWA256 | 10:00a | 2h21m | Tue |
| Southwest SWA256 | 10:09a | 2h8m | Wed |
| Southwest SWA16 | 10:09a | 2h1m | Thu |
| Southwest SWA398 | 11:02a | 2h13m | Sat |
| Southwest SWA1988 | 12:09p | 2h11m | Sun |
| Southwest SWA234 | 1:59p | 2h5m | Thu |
| Southwest SWA1964 | 2:49p | 2h8m | Thu |
| Southwest SWA1966 | 3:03p | 2h13m | Tue |
| Southwest SWA111 | 3:04p | 2h7m | Sun |
| Southwest SWA1964 | 3:12p | 2h9m | Mon |
| Southwest SWA1966 | 3:21p | 2h1m | Wed, Sat |
| Southwest SWA1964 | 3:38p | 2h5m | Fri |
| Southwest SWA152 | 4:32p | 2h15m | Mon |
| Southwest SWA265 | 4:50p | 2h14m | Tue |
| Southwest SWA265 | 5:01p | 2h11m | Wed |
| Southwest SWA1966 | 5:57p | 2h4m | Mon |
| Southwest SWA1966 | 6:16p | 2h | Fri |
| Southwest SWA265 | 6:27p | 2h13m | Sun |
| Southwest SWA1966 | 6:44p | 2h4m | Thu |
| Southwest SWA2771 | 7:49p | 2h10m | Sat |
| Southwest SWA2771 | 8:03p | 2h1m | Fri |
| Southwest SWA2771 | 8:46p | 2h11m | Thu |
| Southwest SWA2771 | 9:02p | 2h22m | Mon |
| Southwest SWA2278 | 9:02p | 2h10m | Tue–Wed |
| Southwest SWA2278 | 11:13p | 2h21m | Sun |
Southwest
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The route
One hop: HOU → MDWDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from Houston Hobby (HOU) to Chicago (MDW)
William P. Hobby Airport (HOU) has 38 nonstop flights a week to Chicago (MDW), operated by Southwest. No layovers, no connections — one hop out of HOU and you're there.
This route flies every day of the week, so any travel day works. Route data updated October 2026 from observed departures.
Route data updated October 2026 from observed flight departures. Schedules change — always confirm with the airline before booking.
How long is the flight from Houston Hobby to Chicago?
The nonstop flight from Houston Hobby (HOU) to Chicago (MDW) takes about 2h9m in the air, based on recently observed nonstop departures.
How long does it take to drive from Houston Hobby to Chicago?
Driving from Houston Hobby to Chicago takes about 16h 17m behind the wheel — roughly 1,084 miles, or about 2 days of real driving. The nonstop flight takes about 2h9m.