Well known for its luxury listings, the Gold Coast neighborhood is one of the most expensive in Chicago. For many neighborhoods, a $9.145 million listing would become its priciest, but for the Gold Coast, this spacious 6,200-square-foot spread is now the neighborhood's third most expensive. The three bedroom, five bathroom penthouse occupies an entire floor at 65 E. Goethe, and boast very high end finishes from designer Scott Himmel. It's also got wide views of Lake Michigan and the downtown skyline. Being located in the heart of the Gold Coast, there's plenty of shopping and dining within walking distance. And while the listing price is no doubt pricey, the monthly assessment is a whopping $6,377.