Thursday, October 8 · typical odds for a Thursday (too early for a weather forecast) · issued Sun 12:00 PM ET · connections flying that day

Thu, Oct 8: American via Philadelphia, leaving 14:44, is the safest bet: 81% chance of reaching Chicago on time.

Best connections that day, one ticket

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Chicago on time, from each leg’s forecast for the day. Total trip = scheduled departure to arrival (Chicago is 1 h behind Key West). Layovers up to 4 hours. Pick a connection for its 12-month details.


American Details →	EYW 14:44 → PHL 18:11AA 4509 · flown by Republic	2h 55m Philadelphia	PHL 21:06 → ORD 22:38AA 2155	8h 54m	100%	81%
Delta Details →	EYW 07:50 → ATL 09:54DL 1072	1h 28m Atlanta	ATL 11:22 → ORD 12:34DL 2894	5h 44m	92%	76%
Delta Details →	EYW 14:24 → ATL 16:31DL 1472	3h 08m Atlanta	ATL 19:39 → ORD 20:51DL 1139	7h 27m	99%	71%
Delta Details →	EYW 11:56 → ATL 14:03DL 1281	1h 47m Atlanta	ATL 15:50 → ORD 17:12DL 2738	6h 16m	93%	69%
American Details →	EYW 14:10 → CLT 16:31AA 1816	1h 55m Charlotte	CLT 18:26 → ORD 19:51AA 2488	6h 41m	89%	62%

How these are worked out. Each flight’s odds are our forecast for that day (typical odds until the weather forecast covers it); flights of airlines we don’t forecast yet use their 12-month record and are marked. Makes the connection: the first flight’s 12-month lateness curve, scaled so its chance of arriving 15+ min late matches the day’s forecast, at the layover minus the 45-minute minimum (90 on separate tickets). Arrives on time: first flight not cancelled × connection made × second flight not cancelled × second flight within 15 minutes, each from the day’s forecast.

About this data: forecast odds from our model for Thu, Oct 8 (newest published update); 12-month records from US DOT on-time data, Aug 2025 – Jul 2026, all US airlines; regional flights count under the airline that sells them. JSON