When I cook chili in a pot, it's covered for the first couple of hours, and then uncovered for about the last 45 minutes of cooking. The uncovered is what allows the chili to thicken to however you like it.

Crock Pot? Maybe if you were to add a package of the chili seasoning, which contains spices and a thickening agent (usually found in the gravy section of the grocery store) it would be more to your liking. Personally, I'll stick to the stove-top.