@Goosegg Would only go to JUCO to develop as a baseball player. Took ACT end of last year and got a 27. That score was without studying, and I am now in a class. Next ACT I expect to be in the 30s, hopefully 32+. GPA and class rigor are all good.
Based on the College Navigator, you'd probably want to shoot a little higher ~34 Composite, 35 English, 33-34 Math on the ACT scores to put you at 50th percentile. This is assuming you have the baseball skills the Univ of Chicago is looking for. If you have these two things covered then you have a fighting chance with Admissions. This is an extremely selective University.
Best of luck going forward!