I live in Kansas City, visited Chicago a while back, and find the city fascinating. I liked reading a few of your posts, because it gave me an insight into everyday Chicago life.
I obviously can’t identify with the rants, but maybe “wannabe Chicagoans” is a niche demographic you could target? Either way, I’m subscribing to your RSS feed.
As far as design, overall it’s good, and I like your header image. But why do the Google Custom Search widget and sidebar ads have black backgrounds? They’d mesh better with the site if they were grey.
Also, you may want to use the header tag a little less. It’s best to have a few paragraphs between each, and not have one directly after the title – this allows readers to more easily scan the post, making them likely to read more posts before leaving the site.
So, I’d say it looks pretty good overall. The #1 piece of advice I can give you is to keep writing.