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

Chicago → Key West via Dallas-Fort Worth: arrives on time 58%

  1. 07:15 ORD → 09:58 DFW
    UA 539 · United · 2h 43m · 82% on time, 0.5% cancelled
  2. 3h 04m layover in Dallas-Fort Worth (DFW) · 90 min minimum on separate tickets
  3. 13:02 DFW → 16:54 EYW
    AA 1814 · American · 2h 52m · 60% on time, 1.2% cancelled

Total trip 8h 39m, scheduled departure to arrival (Key West is 1 h ahead of Chicago). Times are local. Both flew on 56 of the last 56 days.

Makes the connection97%The first flight arrived more than 94 minutes late on 3% of the days it flew: too late for the 90-minute minimum connection on a 3h 04m layover.
Arrives on time58%First flight not cancelled (0.5% are) × connection made (97%) × second flight not cancelled (1.2% are) and within 15 minutes (60%).
Total trip8h 39mORD 07:15 to EYW 16:54, 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.