Hm. Well, the domain/site name is fantastic. But I don't feel any attraction to the place; it's like Digg with a filter that the stories have to mention Chicago

Hm. Well, the domain/site name is fantastic. But I don't feel any attraction to the place; it's like Digg with a filter that the stories have to mention Chicago. There is no consistency. The top 10 items go from sport, political gossip, and food reviews to tech CEO arrests and an article about an upcoming museum exhibit. Is there anyone who would be interested in more than one of those things? Who is the target user? There is no focus; it's just random noise to me. I have one suggestion, even if it's a bit evil: decide the kind of articles your target user is interested in, and then once in a while, go in and vote the crap out of them. Yes it's cheating. But you need momentum and you need to create a positive feedback loop. Seeing a whole page of near-random articles all with 3 or 4 votes is a turn-off and a self-fulfilling prophecy.