In all honesty, You can’t really go wrong here. Both will provide you a stellar education. Please don’t agonize and torture yourself. You will be in a great place next year and be happy. If you have any financial constraints, choose the school that gave you the better deal. That would be UChicago.
If you have any doubts that you are passing up prestige and have no financial constraints chose Harvard. Your family is pretty high income. You don’t want to feel stuck at UChicago thinking why did I pass up Harvard for this?
I think that you may be leaning more to Harvard tbh. With a $35,000 merit scholarship, a kid that really wants UChicago would have gleefully accepted. You seem to be agonizing over this too much.
Let go. Have confidence and move forward. Things will really be OK. Always, buena suerte.