BOS → MDW Southwest Airlines

Southwest Airlines · Boston, MA to Chicago, IL · 1,382 flights, 2025-07-01 to 2026-06-30 · aggregated across 65 flight numbers

This route runs much more reliably at some times of day than others — 94% on-time departing 3–6am vs. 40% departing 9pm–12am.
On-time arrival
74%
Median delay
-3 min
90th percentile
+57 min
Cancellation rate
2%

How on-time is Southwest Airlines from BOS to MDW?

Across every Southwest Airlines flight number on BOS → MDW (1,382 flights, 2025-07-01 to 2026-06-30), 74% arrived within 15 minutes of schedule. Median arrival delay -3 min; the worst 10% ran +57 min or later. 2% were cancelled.

Delay distribution

Arrival delay for completed flights (excludes cancellations and diversions).

ArrivalFlightsShare
Early / on-time99874%
16-30 min1189%
31-60 min1159%
61-120 min786%
2+ hrs423%

Performance by month

MonthFlightsOn-timeAvg delay
2025-0717071%+16 min
2025-0813380%+9 min
2025-0912658%+24 min
2025-1013871%+12 min
2025-118383%+5 min
2025-129073%+15 min
2026-016688%-4 min
2026-025881%-2 min
2026-0310969%+12 min
2026-0411881%+1 min
2026-0512274%+4 min
2026-0613872%+18 min

Performance by day of week

DayFlightsOn-time
Mon20269%
Tue18478%
Wed17579%
Thu19871%
Fri20975%
Sat17982%
Sun20466%

Based on US DOT Bureau of Transportation Statistics on-time data. Loading the full breakdown…