Wow, that's cool and creative. I didn't anticipate that, but think it's fun. Yeah, tuition at Chicago is very expensive, so that's substantial.
My nephew is at U Chicago, and they have a quarter-system that might prove really conducive to Cunningham. Most universities run a semester system which doesn't sync well with the minor-league life. Spring semester conflicts with spring training, and fall semester at most universities begins in August. So there aren't ANY semesters that don't conflict with the minor-league baseball schedule to varying degree.
But Chicago's quarter system is potentially much friendlier. fall term doesn't start until late September; conflicting with Fall instrux but not with any of the minor-league season. Winter quarter finishes in March, so he'd maybe miss some spring training and have a variably delayed start. But minor-league camp doesn't start as early as big-league camp anyway, so he might be only a couple weeks delayed. So he could be carrying both Fall and Winter quarters like a regular student. His academic schedule would obviously be delayed if he's taking off BOTH spring and summer quarters, but being able to take 2/3 of the normal quarters wouldn't disrupt his academic progress all that badly. And he'd be able to experience much of the intellectual and social life that a normal student has access to. Seems like a really cool fit.
I hope it works out for him, and pitch lab has him throwing strikes at 95 within a year or two.