Direct flights from Boston (BOS) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 50% of the last 12 operated flights arrived within 15 minutes of schedule. The median arrival is 12 minutes late. 2 of the 12 tracked flights were cancelled. The nonstop covers 1,382 km, an estimated 2 hours 16 minutes in the air. Measured by Pro Flight Search from live flight boards at Boston and Chicago. Updated 16 October 2026 at 23:20 UTC.
Left BOS at 17:40, 50 min after its 16:50 slot.
Landing estimate from 147,217 tracked flights of 2 to 4 hours that left 30 to 59 min late. The MDW board has not posted a landing time yet. How planes make up time
Track WN2799 →Checked BOS board 19:08 · MDW board 18:20
of the last 12 operated BOS → MDW flights arrived within 15 minutes
Median arrival delay is +12 min. 2 of 12 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
Each mark is a scheduled departure at its origin-local time, observed operating in the last 7 days. Today is highlighted.
Actual board outcomes rather than schedules, paired departure and arrival per flight and day.
Current conditions put the pressure at BOS: 50% 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
Pro Flight Search records official board updates for nonstop BOS 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
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Pro Flight Search — Boston (BOS) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.
https://proflightsearch.com/search-flights/BOS-MDW
Some delays possible. The departure side at BOS is the weaker end, route health score 65/100. The airports section above carries the live status and delay window at both ends.
Operators schedule morning departures around 06:10 and evening departures around 17:55 from BOS. 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.
Great-circle distance is 1,382 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 128–148 min gate-to-gate on this route.
Southwest Airlines runs the route with about 37 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.
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