Agree with lindagaf but I’d do it via phone versus email in case the parent is the type who would snoop.
Trying to “convince” the kinds of people who stupidly worship HYP that “look, Chicago is good too!” Is a fool’s errand. Such people act on mistaken emotional notions, not logic.
Re the girl who regretted not going to Harvard…that is kind of ridiculous. That person did not experience Harvard, so how can she regret what didn’t happen? It’s fine to wonder what might have happened, but I would not base any decision on someone’s “might have been”.
It is not ridiculous… some of her issues were quite specific to the academic environment at UChicago. PM me if you want details.
LOL OP you one sly cat 
Yeah but I suggest you talk to other people close to you (friends, guidance counselor, etc…) and see what they think about it. What does you mom think? Grandparents? If you get them on your side it will be significantly easier to convince your dad. Your dad cares about you and in his eyes he wants you to go the best place possible. Uchicago has done a great job with their marketing the past couple of years but still isn’t a well known as Yale, Harvard, etc… so many parents and adults don’t really see the appeal.
By no means should you tank your admissions. I suggest taking @momcinco 's advice. Try to be understanding and don’t exactly totally rule out other schools yet. Do more research about all the schools.
Your situation isn’t a typical CC dilemma. You only met your dad a few years ago when your mom lost custody, right? Since your mom kept you from him for over a dozen years, he may not have planned to pay for college. After paying for a private high school, he may be banking on schools with generous financial aid (most of them are the difficult to get into, prestigious colleges) to help him cover the expenses. Maybe he had to pay legal fees to get you back from your mom and doesn’t have the money to pay for expensive schools without generous aid. Unless the net costs are the same, there’s probably more going on than just “prestige” hunting. It’s a mistake for you to torpedo your chances. You need to wait until all your acceptances come in and then discuss the finances with your dad. You don’t say whether or not your dad is remarried, if you have siblings he has to plan for, or how close he is to retirement, but those are all things that need to be considered. What will you do if you purposely ruin your chances to get accepted into what may be the only affordable schools on your list just so you can attend your “dream” college then find out your dad can’t, or won’t, pay for it?
As far as I can see this issue may very well not even come up since acceptance rates are SO low. Statistically you won’t get accepted and then you won’t have to deal with it. If it were me I’d cross that bridge when I came to it and not before.
With what was expressed in post #24 there is clearly much more to this situation than the vast majority of us were aware of.
It is quite foolish to tank any elite college admissions possibility, especially so if financial aid is needed to attend. It is irresponsible that posters here would suggest you do that. They have no awareness of your families financial circumstances.
What’s your father’s budget ?
What’s your fa package from uchic ?
Have you run the npc foe the other universities ?
If you don’t get into one of HIS schools will your dad support you going to uchic ? Won’t he make you go to the cheapest school (what is it ?)
Why isn’t your mother involved in any way ?