I knew a few Case law grads, and the thing that would tilt my decision in favor of Case is the amount of recruiting that Jones Day does there.
If you look at the nation's largest law-firms, Cleveland seems to have more than their share. (More and bigger than, say, Detroit.)
OTOH, I don't think the Cleveland market can compare to Chicago. If you're SURE you want to be in Chicago, I think you're always better off to go to a Chicago school.
I went to Case (not law) and compared to Chicago, there is not much to do there. Chicago is probably the funnest big town in the country. Cleveland is like most of the industrial midwest cities where the place empties out at the end of the working day every day. It's not like there's NOTHING to do in Cleveland, but most folks don't live there, they live in the burbs.
There are things to do near the university. There's an area called Coventry which is like a teeny, tiny bohemian district. (The original BW3 is there). The school is also close to Little Italy. Lots of great, cheap italian food.
But seriously, compared to chicago, it's dull, dull, dull. Also, University Circle is kinda nice, but go a quarter mile away in any direction and you're in some of the most dangerous urban area in the country.
Case is also a very, very serious, studious school. Nobody is there for the football team or campus life. It's heavy in engineering and medicine. So, not a big party crowd.
Personally? If it were me? I'd probably pick chicago kent. And I'm actually from near Cleveland and did attend Case. Nothing wrong with the school: it's a great school. It's just not much of a college experience or fun urban setting compared to other places.
Also, keep in mind, I don't know what neighborhood Chicago Kent is in. Parts of Chicago are fun as all get-out (michigan avenue and inside the loop? Not that familiar, been there a few times, but not an expert by any stretch), but I bet there are bad parts and I have no idea where Chicago-Kent is.
Best of luck!