Left MDW at 21:36, 21 min after its 21:15 slot.
Track WN2080 →Direct flights from Chicago (MDW) to San Jose (SJC): 7 nonstop departures observed each week across 1 airline. 78% of the last 9 operated flights arrived within 15 minutes of schedule. The median arrival is 9 minutes early. No cancellations were recorded across the 9 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 Chicago and San Jose. Updated 24 October 2026 at 03:05 UTC.
Today, MDW → SJC
Fri 23 Oct · local times- 09:50 WN2990Southwest Left 10:26 +36 Landed 12:32 +7
- 17:30 1I267NetJets Aviation Sched 17:30Departure not confirmed by the board ·
- 18:08 1I867NetJets Aviation Left 17:58 ·
- 21:15 WN2080Southwest Airlines Left 21:36 +21 ·
Checked MDW board 22:05 · SJC board 15:03
of the last 9 operated MDW → SJC flights arrived within 15 minutes
Median arrival delay is −9 min. 0 of 9 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
The week
scheduled departures · origin local timeEach 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 daysFlights WN2990 09:50 Mo Tu We Th Fr · WN1705 10:00 Su · WN2483 12:50 Sa · WN1281 19:10 Sa
History
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 and SJC: 44% odds of a 15+ minute delay and around +9 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 Jose route actually runs
Pro Flight Search records official board updates for nonstop MDW to SJC 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
Journalists, bloggers, and researchers may cite this page with attribution and a link to Pro Flight Search.
Pro Flight Search — Chicago (MDW) to San Jose (SJC) route reliability, measured from operated flights on official airport boards.
https://proflightsearch.com/search-flights/MDW-SJC
MDW to SJC questions
Is MDW–SJC running on time right now?
Smooth skies ahead. The departure side at MDW is the weaker end, route health score 86/100. The airports section above carries the live status and delay window at both ends.
Morning or evening flight on MDW–SJC?
Operators schedule morning departures around 09:50 and evening departures around 19:10 from MDW. Earlier flights typically land before destination-airport delays accumulate later in the day; check the SJC delay card to confirm conditions when you'd arrive.
How long is the flight from MDW to SJC?
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 MDW–SJC 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.