BR 646 then UA 5758 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
17:10BR 646 from Anchorage at the gate
16:40UA 5758 to Milwaukee leaves the gate
23 h 30 apart on the timetable, overnight
UA 5758 leaves 23 h 30 after BR 646 arrives on the timetable: more than half a day, so not a connection we count.