AA 5477 then UA 4405 at O'Hare
Madison → Chicago → Springfield Branson National
Timetable, Chicago time
08:50AA 5477 from Madison at the gate
21:20UA 4405 to Springfield Branson National leaves the gate
12 h 30 apart on the timetable
UA 4405 leaves 12 h 30 after AA 5477 arrives on the timetable: more than half a day, so not a connection we count.