Southwest AirlinesWN88% on time
Flights WN3457 05:30 Mo Th Fr · WN4113 07:50 Mo Tu We Th Fr Su · WN4535 07:50 Mo Tu We Th Fr Su · WN2842 varies daily
live
Direct flights from Chicago (MDW) to Boston (BOS): 41 nonstop departures observed each week across 1 airline. 88% of the last 8 tracked flights arrived within 15 minutes of schedule. The median arrival is 4 minutes early. No cancellations were recorded across the 17 tracked flights. 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 Chicago and Boston. Updated 6 November 2026 at 09:53 UTC.
Today, MDW → BOS
Fri 6 Nov · local times- 07:50 WN4113Southwest On scheduleGate A19 BOS 11:10scheduled
- 13:00 WN2900Southwest Airlines On scheduleGate B25 ·
- 18:45 WN2902Southwest Airlines Sched 18:45Departure not confirmed by the board ·
Checked MDW board 03:53 · BOS board 04:12
MDW
Chicago
heavy · +32
BOS
Boston
smooth · +0
1,382 km · ~2h 16m est.
Runs reliable · 1 airline · 41x weekly · nonstop
88% on time
of the last 8 tracked MDW → BOS flights arrived within 15 minutes
Median arrival delay is −4 min. 0 of 17 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
Median arrival−4 minacross the last 8 arrivals
Flight time~2h 16mestimated from route distance
Weekly departures41x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 17
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 outcomes11-05LXJ612departed+41
11-031I870departed−11
11-011I862departed+27
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
Conditions are tightest at BOS: a 46% chance of a 15+ minute delay. In this weather, the more delayed of the two airports is typically about +13 min. Both figures come from the two airports' delay records in similar weather. See live delays → · Weather risk by airport →
next sweep in 120s
How the Chicago to Boston route actually runs
Pro Flight Search records official board updates for nonstop MDW to BOS 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: Chicago (MDW) to Boston (BOS) route reliability, measured from operated flights on official airport boards.
Canonical URL
How we measure this →
https://proflightsearch.com/search-flights/MDW-BOS
MDW to BOS questions
Is MDW–BOS running on time right now?
Mostly on schedule. The departure side at MDW is the weaker end, route health score 70/100. The airports section above carries the live status and delay window at both ends.
Morning or evening flight on MDW–BOS?
Operators schedule morning departures around 05:30 and evening departures around 18:45 from MDW. Earlier flights typically land before destination-airport delays accumulate later in the day; check the BOS delay card to confirm conditions when you'd arrive.
How long is the flight from MDW to BOS?
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.
How often does MDW–BOS fly?
Southwest Airlines runs the route with about 41 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.
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