Friday, October 9 · typical odds for a Friday (too early for a weather forecast) · issued Sun 4:00 PM ET · connections flying that day

Fri, Oct 9: Southwest via Midway, leaving 06:00, is the safest bet: 83% chance of reaching Oakland on time.

Best connections that day, one ticket

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Oakland on time, from each leg’s forecast for the day. Total trip = scheduled departure to arrival (Oakland is 3 h behind New York). Layovers up to 4 hours. Pick a connection for its 12-month details.


Southwest Details →	LGA 06:00 → MDW 07:20WN 2464	2h 50m Chicago	MDW 10:10 → OAK 12:40WN 3366	9h 40m	100%	83%
Southwest Details →	LGA 06:55 → DEN 09:05WN 2454	1h 50m Denver	DEN 10:55 → OAK 12:25WN 1577	8h 30m	98%	82%
Southwest Details →	LGA 16:25 → DEN 19:05WN 2456	3h 05m Denver	DEN 22:10 → OAK 23:50WN 1650	10h 25m	93%	69%
Southwest Details →	LGA 17:30 → MDW 19:20WN 4746	2h 20m Chicago	MDW 21:40 → OAK 00:15 +1WN 4042	9h 45m	91%	59%
Southwest Details →	LGA 14:00 → DEN 16:20WN 2455	2h 30m Denver	DEN 18:50 → OAK 20:25WN 1843	9h 25m	97%	59%

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