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 Denver, leaving 05:15, is the safest bet: 90% chance of reaching Oakland on time; the tightest one-ticket connections make it only 71% of the time.

Nonstops that day

All 2 nonstops →


WN 3366 Southwest Flight history →	MDW 10:10	OAK 12:40	16%	3%	0.6%	74%
WN 4042 Southwest Flight history →	MDW 21:40	OAK 00:15	34%	7%	0.7%	48%

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 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	55m Denver	DEN 07:45 → OAK 09:25WN 1240	6h 10m	97%	90%
Southwest Details →	MDW 05:00 → DAL 07:15WN 1377	1h 35m Dallas	DAL 08:50 → OAK 10:30WN 1268	7h 30m	100%	90%
Southwest Details →	MDW 05:10 → LAX 07:25WN 4637	1h 35m Los Angeles	LAX 09:00 → OAK 10:20WN 3014	7h 10m	100%	87%
Southwest Details →	MDW 05:20 → PHX 06:55WN 2858	2h 45m Phoenix	PHX 09:40 → OAK 11:35WN 2680	8h 15m	100%	86%
Southwest Details →	MDW 05:45 → SAN 07:50WN 3103	2h 00m San Diego	SAN 09:50 → OAK 11:25WN 4166	7h 40m	100%	85%
Southwest Details →	MDW 07:30 → LAS 09:20WN 347	1h 30m Las Vegas	LAS 10:50 → OAK 12:30WN 322	7h 00m	100%	85%
Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	2h 35m Denver	DEN 10:55 → OAK 12:25WN 1577	7h 35m	100%	83%
Southwest Details →	MDW 16:40 → PDX 19:00WN 4765	3h 40m Portland	PDX 22:40 → OAK 00:30 +1WN 3205	9h 50m	97%	79%
Tight connection: often missed
Southwest Details →	MDW 16:55 → LAS 18:45WN 2797	1h 05m Las Vegas	LAS 19:50 → OAK 21:25WN 4270	6h 30m	71%	44%
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	50m Denver	DEN 18:50 → OAK 20:25WN 1843	6h 10m	72%	43%

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