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

Boston → San Antonio via Chicago: arrives on time 81%

  1. 05:25 BOS → 07:00 MDW
    WN 3239 · Southwest · 2h 35m · 91% on time, 0.0% cancelled
  2. 3h 35m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 10:35 MDW → 13:15 SAT
    WN 2570 · Southwest · 2h 40m · 81% on time, 0.0% cancelled

Total trip 8h 50m, scheduled departure to arrival (San Antonio is 1 h behind Boston). Times are local. Both flew on 24 of the last 56 days.

Makes the connection100%The first flight arrived more than 170 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 3h 35m layover.
Arrives on time81%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (81%).
Total trip8h 50mBOS 05:25 to SAT 13:15, 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.