JR, not to belabor it, but I think Chicago's academic calendar is key, and enables this in a way that wouldn't apply for Avitia at GCU or Az State in Mesa.
-https://www.uchicago.edu/academics/calendar/
Using this year's calendar, fall term began Sept 27, and winter term was done March 12.
-Usually "term ends" is when faculty grades are due; last-day-of-exams is several days sooner, and not every student has exams on the last day or two, and can often arrange with professor to take them early, if desired.
Minor-league camp pre-Covid usually began ~March 5, IIRC, so Cunningham could probably conservatively get to Mesa for spring training within a week, or perhaps less, of camp opening. With Fall semester not starting till Sept 27, he'd have the entire minor-league season, all he'd miss would be fall instrux.
By contrast, for Avitia who lives near Mesa and will be going to school in Phoenix, spring term runs till the start of May, and fall term starts the last week of August. So he'd miss not only fall instrux, but the end of the minor-league season and the first two months of the spring/summer minor-league life.
Chicago's schedule is just uniquely perfect.