One friend of a daughter went to Chicago. He might have been the strongest student in her middle school class, and one of the two strongest students in math. I honestly do not know if he every had any grade other than A’s through high school. He used to come over during breaks and complain about how much work U.Chicago is.
U.Chicago is a very good university. However, it is academically very demanding. I would not expect it to be a good fit for a student with a 3.3 unweighted GPA.
However, I expect you to do well with some of the other universities on your list. I like the fact that you have identified three safeties, which is how students really should start their college list.