BOS → MDWBoston to Chicago

live

Direct flights from Boston (BOS) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 70% of the last 10 operated flights arrived within 15 minutes of schedule. The median arrival is 5 minutes late. No cancellations were recorded across the 10 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 9 October 2026 at 02:02 UTC.

BOS Boston disrupted · +76
MDW Chicago busy · +19
1,382 km · ~2h 16m est.
dep bank 05:50–22:007x weekly
Runs mixed · 1 airline · 7x weekly · nonstop
70% on time

of the last 10 operated BOS → MDW flights arrived within 15 minutes

Median arrival delay is +5 min. 0 of 10 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival+5 minacross the last 10 operated legs
Flight time~2h 16mestimated from route distance
Weekly departures7x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 10

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 AirlinesWN67% 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
10-081I761arrived−14
10-08WN1955dep +0 → arr+24
10-08WN2799dep +80 → arr+85
10-08WN805dep +0 → arr+5
10-08WN807arrived+15
10-07WN1660arrived+28
10-07WN2046arrived−10
10-07WN4233arrived−5
10-07WN805arrived−11
10-07WN807arrived−6

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 +76 min disrupted 🌤 clear · W 11 kt Full BOS delay board →
MDWChicago +19 min busy 🌤 few clouds · S 3 kt Full MDW delay board →

Weather lens

Current conditions put the pressure at BOS: 43% 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.