Southwest AirlinesWN100% on time
Flights WN1444 05:00 Mo Th Fr · WN4638 varies Tu We Sa Su · WN2085 varies Mo Tu We Th Fr · WN2828 11:50 Su
live
Direct flights from Houston (HOU) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 100% of the last 7 operated flights arrived within 15 minutes of schedule. The median arrival is 21 minutes early. No cancellations were recorded across the 7 tracked flights. The nonstop covers 1,510 km, an estimated 2 hours 26 minutes in the air. Measured by Pro Flight Search from live flight boards at Houston and Chicago. Updated 28 October 2026 at 14:55 UTC.
Today, HOU → MDW
Wed 28 Oct · local times- 07:05 WN4638Southwest Airlines Left 07:03 Landed 09:24 −6
- 09:00 WN2085Southwest Airlines Left 08:56 MDW 11:25In the air · scheduled landing
- 11:50 WN5016Southwest Airlines Est. 12:00 +10Gate 50 MDW 14:15scheduled
- 14:20 WN2087Southwest Airlines On scheduleGate 25 MDW 16:45scheduled
- 18:35 WN4322Southwest Airlines On scheduleGate 23 MDW 21:05scheduled
- 20:45 WN4789Southwest Airlines On scheduleGate 4 MDW 23:15scheduled
Checked HOU board 09:54 · MDW board 09:55
HOU
Houston
smooth · +0
MDW
Chicago
smooth · +0
1,510 km · ~2h 26m est.
Runs reliable · 1 airline · 7x weekly · nonstop
100% on time
of the last 7 operated HOU → MDW flights arrived within 15 minutes
Median arrival delay is −21 min. 0 of 7 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
Median arrival−21 minacross the last 7 operated legs
Flight time~2h 26mestimated from route distance
Weekly departures7x1 direct airline on the leg
The week
scheduled departures · origin local time06121824
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Southwest Airlines
Each mark is a scheduled departure at its origin-local time, observed operating in the last 7 days. Today is highlighted.
Who flies it
observed on the boards · 7 daysHistory
operated legs · board outcomesActual board outcomes rather than schedules, paired departure and arrival per flight and day.
Full board history, day by day →
Airports right now
live boardsWeather lens
Current conditions put the pressure at HOU and MDW: 41% odds of a 15+ minute delay and around +8 min expected when it bites, measured from this route's own weather-matched delay history. See live delays → · Weather risk by airport →
next sweep in 120s
How the Houston to Chicago route actually runs
Pro Flight Search records official board updates for nonstop HOU to MDW flights through the day: schedules, estimates, gate pushes and actual departures. The verdict above comes from operated flights, so it reflects what this route does rather than what the timetable promises.
Planning around a delay? Live airport delays · Weather delay risk map · Will a delayed flight be cancelled? · Do planes make up time in the air? · How we measure
Cite this data
Journalists, bloggers, and researchers may cite this page with attribution and a link to Pro Flight Search.
Suggested citation
Pro Flight Search — Houston (HOU) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.
Canonical URL
How we measure this →
https://proflightsearch.com/search-flights/HOU-MDW
HOU to MDW questions
Is HOU–MDW running on time right now?
Smooth skies ahead. Both endpoints currently score the same, route health score 100/100. The airports section above carries the live status and delay window at both ends.
Morning or evening flight on HOU–MDW?
Operators schedule morning departures around 05:00 and evening departures around 17:30 from HOU. Earlier flights typically land before destination-airport delays accumulate later in the day; check the MDW delay card to confirm conditions when you'd arrive.
How long is the flight from HOU to MDW?
Great-circle distance is 1,510 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 137–159 min gate-to-gate on this route.
How often does HOU–MDW fly?
Southwest Airlines runs the route with about 37 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.
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