Southwest AirlinesWN60% on time
Flights WN559 varies Tu We Sa · WN1009 11:05 Mo Th Fr · WN966 12:55 Tu We · WN2819 20:30 Tu We Su
live
Direct flights from Chicago (MDW) to San Antonio (SAT): 7 nonstop departures observed each week across 1 airline. 60% of the last 5 operated flights arrived within 15 minutes of schedule. The median arrival is on schedule. No cancellations were recorded across the 5 tracked flights. The nonstop covers 1,668 km, an estimated 2 hours 38 minutes in the air. Measured by Pro Flight Search from live flight boards at Chicago and San Antonio. Updated 12 September 2026 at 15:52 UTC.
MDW
Chicago
smooth · +3
SAT
San Antonio
smooth · +0
1,668 km · ~2h 38m est.
Runs mixed · 1 airline · 7x weekly · nonstop
60% on time
of the last 5 operated MDW → SAT flights arrived within 15 minutes
Median arrival delay is −1 min. 0 of 5 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
Median arrival−1 minacross the last 5 operated legs
Flight time~2h 38mestimated 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 MDW: 35% odds of a 15+ minute delay and around +11 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 Chicago to San Antonio route actually runs
Pro Flight Search records official board updates for nonstop MDW to SAT 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 — Chicago (MDW) to San Antonio (SAT) route reliability, measured from operated flights on official airport boards.
Canonical URL
How we measure this →
https://proflightsearch.com/search-flights/MDW-SAT
MDW to SAT questions
Is MDW–SAT running on time right now?
Smooth skies ahead. The departure side at MDW is the weaker end, route health score 96/100. The airports section above carries the live status and delay window at both ends.
Morning or evening flight on MDW–SAT?
Operators schedule morning departures around 11:05 and evening departures around 20:30 from MDW. Earlier flights typically land before destination-airport delays accumulate later in the day; check the SAT delay card to confirm conditions when you'd arrive.
How long is the flight from MDW to SAT?
Great-circle distance is 1,668 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 148–173 min gate-to-gate on this route.
How often does MDW–SAT fly?
Southwest Airlines runs the route with about 14 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.
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