UA 2290 then AA 3735 at DFW
Chicago O'Hare → Dallas-Fort Worth → Gainesville
Timetable, Dallas-Fort Worth time
16:21UA 2290 from Chicago O'Hare at the gate
08:30AA 3735 to Gainesville leaves the gate
16 h 09 apart on the timetable, overnight
AA 3735 leaves 16 h 09 after UA 2290 arrives on the timetable: more than half a day, so not a connection we count.