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

San Diego → Boston via Chicago: arrives on time 90%

  1. 22:40 SAN → 04:40 MDW
    WN 257 · Southwest · 4h 00m · 92% on time, 0.0% cancelled
  2. 3h 00m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 07:40 MDW → 10:55 BOS +1 day
    WN 4611 · Southwest · 2h 15m · 90% on time, 0.0% cancelled

Total trip 9h 15m, scheduled departure to arrival (Boston is 3 h ahead of San Diego). Times are local. Both flew on 23 of the last 56 days.

Makes the connection100%The first flight arrived more than 135 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 3h 00m layover.
Arrives on time90%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (90%).
Total trip9h 15mSAN 22:40 to BOS 10:55, 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.