Friday, October 9 · typical odds for a Friday (too early for a weather forecast) · issued Sat 8:00 PM ET · connections flying that day

Fri, Oct 9: Southwest via Denver, leaving 05:15, is the safest bet: 90% chance of reaching San Jose on time; the tightest one-ticket connections make it only 58% of the time.

Nonstops that day

All 2 nonstops →


WN 3752 Southwest Flight history →	MDW 10:05	SJC 12:30	13%	2%	0.6%	82%
WN 2659 Southwest Flight history →	MDW 20:50	SJC 23:30	26%	7%	0.7%	38%

Best connections that day, one ticket

Most reliable Quickest (80%+ on time)

Ranked by chance you reach San Jose on time, from each leg’s forecast for the day. Total trip = scheduled departure to arrival (San Jose is 2 h behind Chicago). Layovers up to 4 hours. Pick a connection for its 12-month details.


Southwest Details →	MDW 05:15 → DEN 06:50WN 2989	1h 00m Denver	DEN 07:50 → SJC 09:25WN 494	6h 10m	97%	90%
Southwest Details →	MDW 06:30 → LAS 08:20WN 1182	1h 35m Las Vegas	LAS 09:55 → SJC 11:30WN 439	7h 00m	99%	90%
Southwest Details →	MDW 05:10 → LAX 07:25WN 4637	1h 35m Los Angeles	LAX 09:00 → SJC 10:15WN 2431	7h 05m	100%	88%
Southwest Details →	MDW 05:20 → PHX 06:55WN 2858	2h 45m Phoenix	PHX 09:40 → SJC 11:35WN 3336	8h 15m	100%	88%
Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	1h 10m Denver	DEN 09:30 → SJC 11:00WN 2384	6h 10m	97%	85%
Delta Details →	MDW 11:05 → ATL 14:01DL 1063	2h 58m Atlanta	ATL 16:59 → SJC 18:52DL 2136	9h 47m	99%	81%
Southwest Details →	MDW 05:45 → SAN 07:50WN 3103	1h 40m San Diego	SAN 09:30 → SJC 11:00WN 4509	7h 15m	100%	81%
Southwest Details →	MDW 07:30 → LAS 09:20WN 347	2h 50m Las Vegas	LAS 12:10 → SJC 13:45WN 1242	8h 15m	100%	81%
Tight connection: often missed
Southwest Details →	MDW 18:20 → AUS 20:55WN 3171	1h 00m Austin	AUS 21:55 → SJC 23:30WN 400	7h 10m	70%	48%
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	55m Denver	DEN 18:55 → SJC 20:25WN 1727	6h 10m	74%	46%
Southwest Details →	MDW 16:55 → LAS 18:45WN 2797	50m Las Vegas	LAS 19:35 → SJC 21:05WN 3865	6h 10m	58%	38%

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