Southwest AirlinesWN100% on time
Flights WN2671 05:20 Mo Th Fr · WN4295 varies Su · WN3816 10:35 Tu We · WN2986 23:55 daily
live
Direct flights from Oakland (OAK) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 93% of the last 15 operated flights arrived within 15 minutes of schedule. The median arrival is 10 minutes early. No cancellations were recorded across the 15 tracked flights. The nonstop covers 2,961 km, an estimated 4 hours 18 minutes in the air. Measured by Pro Flight Search from live flight boards at Oakland and Chicago. Updated 9 September 2026 at 19:40 UTC.
OAK
Oakland
busy · +17
MDW
Chicago
smooth · +0
2,961 km · ~4h 18m est.
Runs reliable · 1 airline · 7x weekly · nonstop
93% on time
of the last 15 operated OAK → MDW flights arrived within 15 minutes
Median arrival delay is −10 min. 0 of 15 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
Median arrival−10 minacross the last 15 operated legs
Flight time~4h 18mestimated from route distance
Weekly departures7x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 15
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 outcomes09-03KOW733dep +49 → arr+44
Actual 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 OAK and MDW: 45% 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 Oakland to Chicago route actually runs
Pro Flight Search records official board updates for nonstop OAK 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 — Oakland (OAK) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.
Canonical URL
How we measure this →
https://proflightsearch.com/search-flights/OAK-MDW
OAK to MDW questions
Is OAK–MDW running on time right now?
Smooth skies ahead. The departure side at OAK is the weaker end, route health score 89/100. The airports section above carries the live status and delay window at both ends.
Morning or evening flight on OAK–MDW?
Operators schedule morning departures around 05:20 and evening departures around 23:55 from OAK. 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 OAK to MDW?
Great-circle distance is 2,961 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 239–284 min gate-to-gate on this route.
How often does OAK–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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