12whitesox12, it sounds from your posts that you have high aspirations for school and baseball, and are wondering if your baseball abilities will be able to get into a super-selective school. No-one can really say, because it will depend on lots of things, including (especially since you're a position player) how you play (hit) in front of coaches, at Headfirst or elsewhere. The best advice is not to put all your eggs in one basket, or even only a few baskets. There are a lot of great schools with baseball teams, you may not have heard of many of them. Headfirst is great because it has a wide range of HA schools (in terms of, e.g., average ACT), and you will be seen by schools you haven't considered. There are also some HA showcases in the spring and summer in Chicago (Scholarcase, Play to Win - I have no experience with these, but my son got their announcements), in addition to Headfirst/Showball on the coasts.
Do you have high school or travel coaches you can discuss this with? Ask them what they think, and if they are willing to be references for you.
HA D3 recruiting gets very active in August before senior year, and you may not know where you stand before that. Certainly you can email the UChicago coaches (and others) right now, tell them your measurables that can be backed up by your coaches whose contact info you provide, tell them what your schedule is for the summer, and ask where they are going to be recruiting.