OO 225 then UA 4166 at O'Hare
Richmond → Chicago → Madison
Timetable, Chicago time
11:48OO 225 from Richmond at the gate
10:42UA 4166 to Madison leaves the gate
22 h 54 apart on the timetable, overnight
UA 4166 leaves 22 h 54 after OO 225 arrives on the timetable: more than half a day, so not a connection we count.