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

Key West → Chicago via Dallas-Fort Worth: arrives on time 54%

  1. 14:21 EYW → 16:33 DFW
    AA 305 · American · 3h 12m · 72% on time, 2.8% cancelled
  2. 4h 38m layover in Dallas-Fort Worth (DFW) · 45 min minimum on one ticket
  3. 21:11 DFW → 23:36 ORD
    AA 1573 · American · 2h 25m · 61% on time, 6.0% cancelled

Total trip 10h 15m, scheduled departure to arrival (Chicago is 1 h behind Key West). Times are local. Both flew on 0 of the last 56 days, too few to list among the best connections.

Makes the connection98%The first flight arrived more than 233 minutes late on 2% of the days it flew: too late for the 45-minute minimum connection on a 4h 38m layover.
Arrives on time54%First flight not cancelled (2.8% are) × connection made (98%) × second flight not cancelled (6.0% are) and within 15 minutes (61%).
Total trip10h 15mEYW 14:21 to ORD 23:36, 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.