UA 2466 then AA 2753 at DFW
Chicago O'Hare → Dallas-Fort Worth → Valparaiso
Timetable, Dallas-Fort Worth time
18:33UA 2466 from Chicago O'Hare at the gate
16:51AA 2753 to Valparaiso leaves the gate
22 h 18 apart on the timetable, overnight
AA 2753 leaves 22 h 18 after UA 2466 arrives on the timetable: more than half a day, so not a connection we count.