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

San Juan → Chicago via Boston: arrives on time 43%

  1. 14:05 SJU → 18:14 BOS
    DL 1780 · Delta · 4h 09m · 80% on time, 0.9% cancelled
  2. 2h 31m layover in Boston (BOS) · 45 min minimum on one ticket
  3. 20:45 BOS → 22:39 ORD
    DL 2804 · Delta · 2h 57m · 47% on time, 6.4% cancelled

Total trip 9h 37m, scheduled departure to arrival (Chicago is 1 h behind San Juan). Times are local. Both flew on 56 of the last 56 days.

Makes the connection98%The first flight arrived more than 106 minutes late on 2% of the days it flew: too late for the 45-minute minimum connection on a 2h 31m layover.
Arrives on time43%First flight not cancelled (0.9% are) × connection made (98%) × second flight not cancelled (6.4% are) and within 15 minutes (47%).
Total trip9h 37mSJU 14:05 to ORD 22:39, 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.