Connection · two tickets · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026

Chicago → San Juan via Orlando: arrives on time 82%

  1. 09:12 ORD → 13:13 MCO
    UA 1643 · United · 3h 01m · 85% on time, 0.0% cancelled
  2. 2h 12m layover in Orlando (MCO) · 90 min minimum on separate tickets
  3. 15:25 MCO → 18:25 SJU
    WN 2703 · Southwest · 3h 00m · 83% on time, 0.0% cancelled

Total trip 8h 13m, scheduled departure to arrival (San Juan is 1 h ahead of Chicago). Times are local. Both flew on 24 of the last 56 days.

Makes the connection98%The first flight arrived more than 42 minutes late on 2% of the days it flew: too late for the 90-minute minimum connection on a 2h 12m layover.
Arrives on time82%First flight not cancelled (0.0% are) × connection made (98%) × second flight not cancelled (0.0% are) and within 15 minutes (83%).
Total trip8h 13mORD 09:12 to SJU 18:25, 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.