I did not apply to Kent, but Colorado is one of my top choices.
I think CU has a lot of Pros: It is cheap (I got the same scholarship, plus don't forget you will get in-state yrs 2 and 3), Colorado rocks (Denver would be a fun place to practice and Boulder is supposed to be a fun/pretty city) and they have the new law building (don't even think abuot the old one cause you won't ever have to step foot in it...I have heard it is just awful). Kent is supposed to be a real good school too, but I think CU gives you (a bit) more national flexibility. Most likely, with a CU degree you will go to Denver and with Kent stay in Chicago, but I think there is a little more movement outside of the homebase area for CU than Kent. Another thought is that although Chicago is certainly a bigger legal market and can support more lawyers, there is a lot of law schools in Chicago, and some top-notch ones (U of C, Northwestern) while CU is the clear top school in Colorado, so probably holds a lot of pull in the area. (this is my pure speculation as I am not from around there)
As to your concern of nto knowing people, I wouldn't worry about it. Law school is almost like High School with classes under 200. Even if you don't know anyone when you start (I wouldn't know anyone at any of my top choices) You will get to know everyone really well.
I am going to visit Boulder in a few weeks and am really looking forward to it.