OO 225 then UA 3487 at O'Hare
Richmond → Chicago → Key West
Timetable, Chicago time
11:48OO 225 from Richmond at the gate
10:58UA 3487 to Key West leaves the gate
23 h 10 apart on the timetable, overnight
UA 3487 leaves 23 h 10 after OO 225 arrives on the timetable: more than half a day, so not a connection we count.