AA 1007 then UA 5435 at O'Hare
Charlotte Amalie → Chicago → Indianapolis
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
15:35UA 5435 to Indianapolis leaves the gate
19 h 35 apart on the timetable, overnight
UA 5435 leaves 19 h 35 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.