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 08:15, is the safest bet: 79% chance of reaching Chicago on time; the tightest one-ticket connections make it only 65% of the time.

Nonstops that day

All 2 nonstops →


WN 2744 Southwest Flight history →	OAK 05:10	MDW 11:15	6%	1%	0.6%	88%
WN 3059 Southwest Flight history →	OAK 23:55	MDW 06:00	17%	4%	0.6%	66%

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 Oakland). Layovers up to 4 hours. Pick a connection for its 12-month details.


Southwest Details →	OAK 05:00 → LAS 06:30WN 2325	1h 50m Las Vegas	LAS 08:20 → MDW 13:55WN 2271	6h 55m	97%	87%
Southwest Details →	OAK 19:00 → ONT 20:20WN 271	3h 35m Ontario	ONT 23:55 → MDW 05:40 +1WN 3153	8h 40m	100%	86%
Southwest Details →	OAK 05:30 → AUS 10:55WN 3034	2h 30m Austin	AUS 13:25 → MDW 15:55WN 359	8h 25m	99%	79%
Southwest Details →	OAK 08:15 → DEN 11:40WN 3042	1h 20m Denver	DEN 13:00 → MDW 16:20WN 1601	6h 05m	100%	79%
Southwest Details →	OAK 05:05 → PHX 07:00WN 3066	3h 00m Phoenix	PHX 10:00 → MDW 15:15WN 4066	8h 10m	97%	78%
Southwest Details →	OAK 07:35 → LAS 09:05WN 4348	2h 15m Las Vegas	LAS 11:20 → MDW 16:50WN 4506	7h 15m	100%	78%
Southwest Details →	OAK 18:25 → SAN 20:00WN 3077	2h 40m San Diego	SAN 22:40 → MDW 04:40 +1WN 257	8h 15m	91%	76%
Southwest Details →	OAK 13:25 → DEN 16:50WN 3043	4h 00m Denver	DEN 20:50 → MDW 00:15 +1WN 1615	8h 50m	100%	76%
Tight connection: often missed
Southwest Details →	OAK 13:55 → HOU 19:40WN 4244	55m Houston	HOU 20:35 → MDW 23:05WN 2044	7h 10m	65%	47%
Southwest Details →	OAK 16:00 → LAX 17:25WN 3053	55m Los Angeles	LAX 18:20 → MDW 00:20 +1WN 4541	6h 20m	67%	44%

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