- Know the hoods Don't just know where they're located, know what they look like, smell like, sound like. I have no problem with authors taking fictional liberties, as long as they fit. Each Chicago neighborhood has a different personality so make sure your characters live and work in a neighborhood that suits them. Once you know the neighborhood, you can utilize it. For example, the Cabrini Green housing projects used to be located (they're in the process of tearing them down) smack dab in between the affluent neighborhoods of Lincoln Park and the Gold Coast. Putting your character in that area would call for conflict and/or heighten the existing tension.
- Know the streets You would think with Mapquest and Google Earth that authors would stop making mistakes when it comes to streets. But they don't. Chicago works on a grid, which makes it easier, but there are still plenty of books with parallel streets intersecting, freeway exits that don't exist, and other types of silly errors. Want to show a reader you don't live in the city? Making these mistakes is the easiest way to do it.
- Know the food Do not have your character put ketchup on their hot dog or drink a Miller Lite at a Cubs game or order a Pepsi at the Billy Goat Tavern. Chicagoans love their food and they love it a certain way. Double check with a hardcore Chicagoan before handing in any scenes in bars or restaurants.
- Know the crimes Whenever I would travel abroad and tell people I was from Chicago, I would hear one of two things. At the time it was either, "Oh! Michael Jordan!" or "Chicago! Bang bang!" Historically, Chicago is known for two main things: organized crime and crooked politicians. Now, it's lots of gang and race related violence... and still lots of crooked politicians. When I read Chicago crime fiction, I expect these crimes to be a part of the story in one way or another.
To me, Chicago is a perfect place to set a novel, but if you're gonna do it, do it right. With all the technology we have at our disposal, there's no reason to make mistakes. And, to be perfectly honest, I have put down books because the author made too many mistakes like these. As with any type of writing, research is key. But ultimately, it's the passion for the city that makes the setting come alive on the page.