tailodds FORECAST
Connection · one ticket · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026

Boston → San Diego via Chicago: arrives on time 21%

  1. 18:15 BOS → 20:05 MDW
    WN 3911 · Southwest · 2h 50m · 43% on time, 5.9% cancelled
  2. 1h 05m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 21:10 MDW → 23:25 SAN
    WN 2884 · Southwest · 4h 15m · 52% on time, 8.8% cancelled

Total trip 8h 10m, scheduled departure to arrival (San Diego is 3 h behind Boston). Times are local. Both flew on 47 of the last 56 days.

Makes the connection47%The first flight arrived more than 20 minutes late on 53% of the days it flew: too late for the 45-minute minimum connection on a 1h 05m layover.
Arrives on time21%First flight not cancelled (5.9% are) × connection made (47%) × second flight not cancelled (8.8% are) and within 15 minutes (52%).
Total trip8h 10mBOS 18:15 to SAN 23:25, layover included

Tight connection: often missed. The first flight is late enough to miss it on more than 1 day in 4.

Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.