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

Key West → Philadelphia via Chicago: arrives on time 60%

  1. 16:17 EYW → 19:05 ORD
    AA 3996 · American, flown by Envoy · 3h 48m · 71% on time, 2.8% cancelled
  2. 2h 40m layover in Chicago (ORD) · 90 min minimum on separate tickets
  3. 21:45 ORD → 00:57 PHL +1 day
    UA 1744 · United · 2h 12m · 74% on time, 5.9% cancelled

Total trip 8h 40m, scheduled departure to arrival. Times are local. Both flew on 36 of the last 56 days.

Makes the connection88%The first flight arrived more than 70 minutes late on 12% of the days it flew: too late for the 90-minute minimum connection on a 2h 40m layover.
Arrives on time60%First flight not cancelled (2.8% are) × connection made (88%) × second flight not cancelled (5.9% are) and within 15 minutes (74%).
Total trip8h 40mEYW 16:17 to PHL 00:57, 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.