AA 9908 then UA 5996 at O'Hare
Milwaukee → Chicago → Colorado Springs
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
08:55UA 5996 to Colorado Springs leaves the gate
19 h 05 apart on the timetable, overnight
UA 5996 leaves 19 h 05 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.