BOS → MDWBoston to Chicago

live

Direct flights from Boston (BOS) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 31% of the last 13 operated flights arrived within 15 minutes of schedule. The median arrival is 29 minutes late. No cancellations were recorded across the 13 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 Boston and Chicago. Updated 10 October 2026 at 02:55 UTC.

BOS Boston disrupted · +88
MDW Chicago busy · +20
1,382 km · ~2h 16m est.
dep bank 05:50–22:007x weekly
Runs rough · 1 airline · 7x weekly · nonstop
31% on time

of the last 13 operated BOS → MDW flights arrived within 15 minutes

Median arrival delay is +29 min. 0 of 13 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival+29 minacross the last 13 operated legs
Flight time~2h 16mestimated from route distance
Weekly departures7x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 13

The week

scheduled departures · origin local time
06121824
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 days
Southwest AirlinesWN25% on time

Flights WN805 varies Mo Tu We Th Fr Sa · WN1955 07:05 Mo Th Fr · WN2046 10:55 Tu We · WN807 varies daily

History

operated legs · board outcomes
10-09WN1955dep +0 → arr+26
10-09WN2799dep +48 → arr+50
10-09WN4233departed+161
10-09WN805dep +0 → arr+6
10-09WN807dep +36 → arr+41
10-09WN909departed+29
10-081I761arrived−14
10-08WN1955arrived+24
10-08WN2799arrived+85
10-08WN4233arrived+50
10-08WN805arrived+5
10-08WN807arrived+15
10-08WN909arrived+61

Actual board outcomes rather than schedules, paired departure and arrival per flight and day.

Full board history, day by day →

Airports right now

live boards
BOSBoston +88 min disrupted 🌤 few clouds · W 14 kt Full BOS delay board →
MDWChicago +20 min busy 🌤 overcast · ESE 5 kt Full MDW delay board →

Weather lens

Current conditions put the pressure at BOS: 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 →

How the Boston to Chicago route actually runs

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

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 — Boston (BOS) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.

Canonical URL
https://proflightsearch.com/search-flights/BOS-MDW
How we measure this →

BOS to MDW questions

Is BOS–MDW running on time right now?

Significant delay risk. The departure side at BOS is the weaker end, route health score 37/100. The airports section above carries the live status and delay window at both ends.

Morning or evening flight on BOS–MDW?

Operators schedule morning departures around 07:05 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.

How long is the flight from BOS to MDW?

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 BOS–MDW fly?

Southwest Airlines runs the route with about 33 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.