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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 San Jose, leaving 18:25, is the safest bet: 86% 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 2 h ahead of Santa Ana). Layovers up to 4 hours. Pick a connection for its 12-month details.
SouthwestDetails → SNA 18:25 → SJC 19:40WN 342 3h 15m San Jose SJC 22:55 → MDW 05:00 +1WN 3886 8h 35m 100% 86%
SouthwestDetails → SNA 18:45 → SMF 20:10WN 3872 3h 40m Sacramento SMF 23:50 → MDW 05:45 +1WN 3802 9h 00m 100% 85%
SouthwestDetails → SNA 06:45 → SJC 08:15WN 3858 1h 50m San Jose SJC 10:05 → MDW 16:10WN 4357 7h 25m 100% 83%
SouthwestDetails → SNA 18:35 → OAK 20:00WN 3853 3h 55m Oakland OAK 23:55 → MDW 06:00 +1WN 3059 9h 25m 100% 82%
SouthwestDetails → SNA 07:05 → PHX 08:30WN 3887 1h 30m Phoenix PHX 10:00 → MDW 15:15WN 4066 6h 10m 100% 80%
SouthwestDetails → SNA 06:45 → SMF 08:25WN 2669 3h 35m Sacramento SMF 12:00 → MDW 17:55WN 3769 9h 10m 100% 79%
SouthwestDetails → SNA 07:00 → DEN 10:25WN 4011 2h 35m Denver DEN 13:00 → MDW 16:20WN 1601 7h 20m 100% 79%
SouthwestDetails → SNA 19:00 → LAS 20:10WN 2477 3h 45m Las Vegas LAS 23:55 → MDW 05:25 +1WN 2276 8h 25m 100% 78%
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