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Any day
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: American via Miami, leaving 05:00, is the safest bet: 68% chance of reaching Key West on time.

Nonstops that day

All 2 nonstops →
UA 3690 United flown by Republic Flight history → ORD 10:55 EYW 15:19 22% 5% 4.8% 89%worse than usual
AA 3996 American flown by Envoy Flight history → ORD 11:29 EYW 15:50 23% 5% 7.4% 81%

Best connections that day, one ticket

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

DeltaDetails → ORD 05:30 → ATL 08:29DL 1264 3h 01m Atlanta ATL 11:30 → EYW 13:23DL 1472 6h 53m 99% 81%
AmericanDetails → ORD 05:00 → PHL 08:05AA 2970 2h 25m Philadelphia PHL 10:30 → EYW 13:40AA 1898 7h 40m 96% 80%
AmericanDetails → ORD 05:07 → CLT 08:10AA 2842 1h 50m Charlotte CLT 10:00 → EYW 12:14AA 1826 6h 07m 97% 77%
DeltaDetails → ORD 11:20 → ATL 14:25DL 1147 3h 33m Atlanta ATL 17:58 → EYW 19:56DL 2815 7h 36m 99% 76%
AmericanDetails → ORD 05:00 → MIA 09:09AA 2984 3h 01m Miami MIA 12:10 → EYW 13:14AA 3518 · flown by Envoy 7h 14m 100% 74%
DeltaDetails → ORD 09:45 → ATL 12:51DL 1178 2h 34m Atlanta ATL 15:25 → EYW 17:23DL 2168 6h 38m 99% 73%
UnitedDetails → ORD 06:00 → EWR 09:12UA 2295 1h 06m Newark EWR 10:18 → EYW 13:30UA 1418 6h 30m 96% 72%
AmericanDetails → ORD 10:05 → MIA 14:18AA 1474 3h 47m Miami MIA 18:05 → EYW 19:06AA 3517 · flown by Envoy 8h 01m 100% 70%
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