UA 3911 then AA 2279 at O'Hare
Portland (Oregon) → Chicago → San Juan
Timetable, Chicago time
17:09UA 3911 from Portland (Oregon) at the gate
08:05AA 2279 to San Juan leaves the gate
14 h 56 apart on the timetable, overnight
AA 2279 leaves 14 h 56 after UA 3911 arrives on the timetable: more than half a day, so not a connection we count.