Friday, October 9 · typical odds for a Friday (too early for a weather forecast) · issued Mon 12:00 PM ET · connections flying that day

Fri, Oct 9: Delta via Atlanta, leaving 07:50, is the safest bet: 75% chance of reaching Chicago on time; the tightest one-ticket connections make it only 63% of the time.

Nonstops that day

All 2 nonstops →


UA 3499 United flown by Republic Flight history →	EYW 16:00	ORD 18:55	29%	12%	6.0%	85%worse than usual
AA 3996 American flown by Envoy Flight history →	EYW 16:21	ORD 19:17	38%	11%	7.3%	71%

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.


Delta Details →	EYW 07:50 → ATL 09:54DL 1072	3h 08m Atlanta	ATL 13:02 → ORD 14:14DL 1477	7h 24m	96%	77%
American Details →	EYW 16:41 → CLT 19:12AA 3519 · flown by Envoy	3h 27m Charlotte	CLT 22:39 → ORD 00:01 +1AA 3014	8h 20m	97%	75%
Delta Details →	EYW 18:18 → ATL 20:32DL 2168	2h 08m Atlanta	ATL 22:40 → ORD 23:53DL 1199	6h 35m	94%	72%
American Details →	EYW 12:18 → DCA 15:18AA 4416 · flown by Republic	2h 04m Washington	DCA 17:22 → ORD 18:54AA 1630	7h 36m	97%	71%
American Details →	EYW 13:01 → CLT 15:25AA 1826	3h 01m Charlotte	CLT 18:26 → ORD 19:51AA 2488	7h 50m	98%	69%
American Details →	EYW 17:34 → PHL 20:40AA 3147	2h 23m Philadelphia	PHL 23:03 → ORD 00:29 +1AA 2840	7h 55m	86%	69%
American Details →	EYW 14:21 → DFW 16:33AA 305	2h 55m Dallas-Fort Worth	DFW 19:28 → ORD 22:15AA 3531 · flown by Envoy	8h 54m	91%	68%
Delta Details →	EYW 14:24 → ATL 16:31DL 1472	2h 44m Atlanta	ATL 19:15 → ORD 20:33DL 2486	7h 09m	98%	67%
Tight connection: often missed
American Details →	EYW 13:01 → CLT 15:25AA 1826	51m Charlotte	CLT 16:16 → ORD 17:39AA 536	5h 38m	73%	55%
American Details →	EYW 17:34 → PHL 20:40AA 3147	52m Philadelphia	PHL 21:32 → ORD 23:30AA 3042	6h 56m	63%	50%
American Details →	EYW 14:21 → DFW 16:33AA 305	1h 01m Dallas-Fort Worth	DFW 17:34 → ORD 20:29AA 1893	7h 08m	68%	45%

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 Fri, Oct 9 (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