Southwest AirlinesWN92% on time
Flights WN208 09:55 Tu We Sa · WN1286 11:20 Mo Th Fr · WN3607 23:00 daily
live
Direct flights from San Jose (SJC) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 92% of the last 13 operated flights arrived within 15 minutes of schedule. The median arrival is 7 minutes early. No cancellations were recorded across the 13 tracked flights. The nonstop covers 2,950 km, an estimated 4 hours 17 minutes in the air. Measured by Pro Flight Search from live flight boards at San Jose and Chicago. Updated 10 September 2026 at 03:26 UTC.
SJC
San Jose
smooth · +6
MDW
Chicago
smooth · +0
2,950 km · ~4h 17m est.
Runs reliable · 1 airline · 7x weekly · nonstop
92% on time
of the last 13 operated SJC → MDW flights arrived within 15 minutes
Median arrival delay is −7 min. 0 of 13 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
Median arrival−7 minacross the last 13 operated legs
Flight time~4h 17mestimated from route distance
Weekly departures7x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 13
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 SJC and MDW: 44% 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 San Jose to Chicago route actually runs
Pro Flight Search records official board updates for nonstop SJC 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 Jose (SJC) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.
Canonical URL
How we measure this →
https://proflightsearch.com/search-flights/SJC-MDW
SJC to MDW questions
Is SJC–MDW running on time right now?
Smooth skies ahead. The departure side at SJC is the weaker end, route health score 95/100. The airports section above carries the live status and delay window at both ends.
Morning or evening flight on SJC–MDW?
Operators schedule morning departures around 09:55 and evening departures around 23:00 from SJC. 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 SJC to MDW?
Great-circle distance is 2,950 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 238–283 min gate-to-gate on this route.
How often does SJC–MDW fly?
Southwest Airlines runs the route with about 13 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.
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