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

Chicago → San Juan via New York: arrives on time 78%

  1. 06:05 ORD → 09:26 JFK
    DL 5741 · Delta, flown by Republic · 2h 21m · 89% on time, 1.8% cancelled
  2. 3h 04m layover in New York (JFK) · 45 min minimum on one ticket
  3. 12:30 JFK → 16:29 SJU
    DL 1961 · Delta · 3h 59m · 84% on time, 1.1% cancelled

Total trip 9h 24m, scheduled departure to arrival (San Juan is 1 h ahead of Chicago). Times are local. Both flew on 55 of the last 56 days.

Makes the connection96%The first flight arrived more than 139 minutes late on 4% of the days it flew: too late for the 45-minute minimum connection on a 3h 04m layover.
Arrives on time78%First flight not cancelled (1.8% are) × connection made (96%) × second flight not cancelled (1.1% are) and within 15 minutes (84%).
Total trip9h 24mORD 06:05 to SJU 16:29, 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.