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Any day
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 05:10, is the safest bet: 84% chance of reaching Chicago on time; the tightest one-ticket connections make it only 61% of the time.

Nonstops that day

All 2 nonstops →
WN 1779 Southwest Flight history → SFO 05:50 MDW 12:00 6% 1% 0.7% 83%
WN 3649 Southwest Flight history → SFO 23:40 MDW 05:55 36% 6% 0.6% 41%

Best connections that day, one ticket

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

SouthwestDetails → SFO 05:00 → LAS 06:35WN 4231 1h 45m Las Vegas LAS 08:20 → MDW 13:55WN 2271 6h 55m 100% 90%
SouthwestDetails → SFO 05:10 → DEN 08:40WN 1424 1h 20m Denver DEN 10:00 → MDW 13:25WN 755 6h 15m 96% 84%
SouthwestDetails → SFO 05:30 → PHX 07:30WN 4145 2h 30m Phoenix PHX 10:00 → MDW 15:15WN 4066 7h 45m 100% 80%
SouthwestDetails → SFO 18:10 → SAN 19:45WN 4681 2h 55m San Diego SAN 22:40 → MDW 04:40 +1WN 257 8h 30m 97% 80%
DeltaDetails → SFO 06:00 → ATL 13:44DL 570 1h 31m Atlanta ATL 15:15 → MDW 16:15DL 1728 8h 15m 96% 80%
DeltaDetails → SFO 11:38 → ATL 19:27DL 693 1h 48m Atlanta ATL 21:15 → MDW 22:15DL 1076 8h 37m 94% 75%
DeltaDetails → SFO 00:35 → MSP 06:09DL 2789 46m Minneapolis MSP 06:55 → MDW 08:37DL 4712 · flown by Endeavor 6h 02m 89% 74%
SouthwestDetails → SFO 14:35 → DEN 18:10WN 3641 2h 40m Denver DEN 20:50 → MDW 00:15 +1WN 1615 7h 40m 95% 72%
Tight connection: often missed
SouthwestDetails → SFO 21:05 → LAX 22:40WN 3648 1h 15m Los Angeles LAX 23:55 → MDW 05:55 +1WN 2413 6h 50m 65% 49%
SouthwestDetails → SFO 14:00 → SAN 15:40WN 4242 1h 50m San Diego SAN 17:30 → MDW 23:30WN 3448 7h 30m 67% 44%
SouthwestDetails → SFO 13:20 → LAS 15:00WN 3644 1h 05m Las Vegas LAS 16:05 → MDW 21:45WN 2274 6h 25m 61% 42%
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