Tickets
Any day
Wednesday, October 7 · typical odds for a Wednesday (too early for a weather forecast) · issued Sat 12:00 PM ET · connections flying that day

Wed, Oct 7: Delta via Atlanta, leaving 05:30, is the safest bet: 82% chance of reaching San Juan on time; the tightest one-ticket connections make it only 43% of the time.

Nonstops that day

All 1 nonstop →
UA 1996 United Flight history → ORD 08:49 SJU 14:44 22% 6% 1.1% 81%

Best connections that day, one ticket

Ranked by chance you reach San Juan on time, from each leg’s forecast for the day. Total trip = scheduled departure to arrival (San Juan is 1 h ahead of Chicago). Layovers up to 4 hours. Pick a connection for its 12-month details.

UnitedDetails → ORD 08:51 → IAH 11:51UA 535 3h 12m Houston IAH 15:03 → SJU 20:38UA 701 10h 47m 100% 85%
DeltaDetails → ORD 06:35 → ATL 09:37DL 1247 3h 23m Atlanta ATL 13:00 → SJU 16:39DL 1946 9h 04m 99% 84%
UnitedDetails → ORD 06:00 → DEN 07:42UA 2806 2h 01m Denver DEN 09:43 → SJU 17:38UA 1339 10h 38m 100% 84%
AmericanDetails → ORD 05:07 → CLT 08:10AA 2842 2h 53m Charlotte CLT 11:03 → SJU 14:50AA 783 8h 43m 98% 83%
DeltaDetails → ORD 05:30 → ATL 08:29DL 1264 1h 16m Atlanta ATL 09:45 → SJU 13:32DL 1882 7h 02m 94% 82%
AmericanDetails → ORD 05:00 → MIA 09:09AA 2984 1h 56m Miami MIA 11:05 → SJU 13:50AA 1613 7h 50m 99% 82%
AmericanDetails → ORD 06:01 → MIA 10:24AA 2452 2h 41m Miami MIA 13:05 → SJU 15:55AA 967 8h 54m 100% 80%
AmericanDetails → ORD 05:00 → PHL 08:05AA 2970 1h 15m Philadelphia PHL 09:20 → SJU 13:33AA 614 7h 33m 94% 79%
Tight connection: often missed
FrontierDetails → ORD 08:05 → FLL 12:22F9 2205 55m Fort Lauderdale FLL 13:17 → SJU 16:05F9 3018 7h 00m 67% 48%
JetBlueDetails → ORD 07:00 → FLL 11:14B6 664 51m Fort Lauderdale FLL 12:05 → SJU 14:42B6 1453 6h 42m 43% 32%
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 Wed, Oct 7 (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