Southwest AirlinesWN60% on time
Flights WN2772 06:15 Tu We · WN4237 06:15 Mo Th Fr · WN1785 06:30 Sa · WN3370 11:15 Tu We
live
Direct flights from San Diego (SAN) to Chicago (MDW): 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 4 minutes early. No cancellations were recorded across the 5 tracked flights. The nonstop covers 2,776 km, an estimated 4 hours 4 minutes in the air. Measured by Pro Flight Search from live flight boards at San Diego and Chicago. Updated 19 October 2026 at 08:38 UTC.
Today, SAN → MDW
Mon 19 Oct · local times- 06:15 WN4237Southwest Airlines On scheduleGate 112 MDW 12:10scheduled
- 11:55 WN1252Southwest Airlines On scheduleGate 112 MDW 17:45scheduled
Checked SAN board 01:38 · MDW board 03:09
SAN
San Diego
heavy · +54
MDW
Chicago
busy · +29
2,776 km · ~4h 04m est.
Runs mixed · 1 airline · 7x weekly · nonstop
60% on time
of the last 5 operated SAN → MDW flights arrived within 15 minutes
Median arrival delay is −4 min. 0 of 5 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
Median arrival−4 minacross the last 5 operated legs
Flight time~4h 04mestimated 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 SAN: 54% odds of a 15+ minute delay and around +19 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 San Diego to Chicago route actually runs
Pro Flight Search records official board updates for nonstop SAN 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 — San Diego (SAN) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.
Canonical URL
How we measure this →
https://proflightsearch.com/search-flights/SAN-MDW
SAN to MDW questions
Is SAN–MDW running on time right now?
Significant delay risk. The departure side at SAN is the weaker end, route health score 45/100. The airports section above carries the live status and delay window at both ends.
Morning or evening flight on SAN–MDW?
Operators schedule morning departures around 06:15 and evening departures around 18:45 from SAN. 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 SAN to MDW?
Great-circle distance is 2,776 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 226–268 min gate-to-gate on this route.
How often does SAN–MDW fly?
Southwest Airlines runs the route with about 23 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.
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