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

Boston → San Diego via Chicago: arrives on time 51%

  1. 07:30 BOS → 09:10 MDW
    WN 745 · Southwest · 2h 40m · 91% on time, 1.8% cancelled
  2. 58m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 10:08 MDW → 12:15 SAN
    WN 4648 · Southwest · 4h 08m · 58% on time, 0.0% cancelled

Total trip 7h 46m, 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 connection90%The first flight arrived more than 13 minutes late on 10% of the days it flew: too late for the 45-minute minimum connection on a 58m layover.
Arrives on time51%First flight not cancelled (1.8% are) × connection made (90%) × second flight not cancelled (0.0% are) and within 15 minutes (58%).
Total trip7h 46mBOS 07:30 to SAN 12:15, layover included

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