AA 1007 then AA 6255 at O'Hare
Charlotte Amalie → Chicago → Sioux Falls
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
12:59AA 6255 to Sioux Falls leaves the gate
16 h 59 apart on the timetable, overnight
AA 6255 leaves 16 h 59 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.