AA 2603 then UA 3234 at Houston
Chicago → Houston → Midland
Timetable, Houston time
10:15AA 2603 from Chicago at the gate
06:45UA 3234 to Midland leaves the gate
20 h 30 apart on the timetable, overnight
UA 3234 leaves 20 h 30 after AA 2603 arrives on the timetable: more than half a day, so not a connection we count.