I'm glad I don't have that problem. According to my kids facebook page he is already at Stanford. 
But I agree with James G. First two questions are how far and what size? Then you can go from there.
What's being considered when evaluating school size? I didn't attend college but I'm encouraging my son to.
I think there are three general sizes. The large mega schools -- think Big 10 -- with 30,000+ kids. These have the big time major ESPN "college" sports -- football, basket ball, etc. This creates "events" -- Ohio State vs. Michigan. There are a lot of educational and entertainment options. But you're the small fish in big pond -- it's a cattle call. If baseball is an option, then it shrinks that pond.
Then there are the medium sized schools - 10,000-15,000 or so kids. Think ISU, SIU, Northern Ill, etc. Kind of a blend to between mega and small. Still a lot of opportunities.
Finally, the small school -- 5000 kids. Think Bradley or Benedictine. They would provide a more intimate learning experience. But will have less of a choice in opportunities. Kind of like going to a large high school.
Then you have location. Urban (think DePaul), Suburban (Northwestern), Rural (NIU), and "college town" (Carbondale?). Obviously it depends on what you're used to. A city kid may be lost in a rural setting and the farmer is out of sorts in the city.
Here is my take from my experience. I had to choose between a small/med. high academic div. 3 school where I could play football and a western Pac 10 party school. I had almost no guidance from my parents. At 18, I didn't realize the educational opportunity at the div 3 school that football would help me to get in to. The girls where ugly. I made my decision based on snow and girls (isn't that was 18 year olds do?). I went to the Pac 10 party school. I ended up transferring to a Big 10 school in the Midwest -- a much better fit for me.
So the best thing you can do for your kid is provide guidance -- don't let him make a decision based on girls/weather. Focus him on location, size, educational opportunity, and if available baseball. If I where you, I would start with the conferences close to home and branch out from there. Look at Big "Ten", MAC, and some of the division 3s in IL/Wisconsin. With the internet today, you can review a few dozen of those schools and see if anything fits. Good luck.