If you live in the Chicago area I would like to know your knowledge of your city. What are some of the best places to shop/dine at? What streets shouldn't you get caught on after the sun goes down? What parts of town are "stuck-up" or for the richer majority of the population? I'm looking to set a story in Chicago but have never physically lived there and am looking for your insight of the town as a whole and little places that most tourists wouldn't know about. Thank you in advance :]
That's a tall order, but here are some thoughts. Michigan avenue hosts some prestigious shops. Be prepared to pay a lot of money for the finer things. A positive that I've noticed here is there aren't as many beggars as there are on the routes leading from the train stations to this avenue. In my mind, the "Gold Coast" is synonymous with wealthier people. This goes back a decade-and-a-half at least, but one of the routes that took us to the bars on Rush street had us going through Cabrini-Green. It was pretty nerve-wracking at the time, being a housing-project and all. But that may have been just the suburbanite in me talking.