CA 3103 then UA 4802 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
15:07CA 3103 from Anchorage at the gate
13:55UA 4802 to Milwaukee leaves the gate
22 h 48 apart on the timetable, overnight
UA 4802 leaves 22 h 48 after CA 3103 arrives on the timetable: more than half a day, so not a connection we count.