AA 4504 then UA 1996 at O'Hare
South Bend → Chicago → San Juan
Timetable, Chicago time
18:35AA 4504 from South Bend at the gate
08:52UA 1996 to San Juan leaves the gate
14 h 17 apart on the timetable, overnight
UA 1996 leaves 14 h 17 after AA 4504 arrives on the timetable: more than half a day, so not a connection we count.