La Scarola at Grand and Milwaukee. It was Joey "The Clown" Lombardo's favorite restaurant before he had to go on the lam. It also has very good old school Italian-American food.
The bar next door--Richard's--is also full of "character." You'll see more of it during a weekday afternoon than you will at night when it turns into a dive bar for younger Gold Coast/Lincoln Park types. Richard's is reputedly where Tony "The Ant" Spilotro stabbed a guy in the throat with a pen, later immortalized by Joe Pesci's character in Casino.