Not that Pitbull would ever own a place in Chicago, but if he did, he'd probably buy something like this. Located in The Chandler at Lakeshore East, this four bedroom, four bathroom, 5,000-square-foot corner unit is really the proper stage for some supreme penthouse parties. Not only is the place dressed to the nines with high-end finishes, it also features three private terraces that look out onto Lake Michigan, Streeterville and River North. And to make sure the party never ends, this penthouse features a legit bar space and a 1,500-bottle wine storage cellar. While Miami-based rappers might not have much interest in living in Chicago, this place is certainly seeking a buyer with deep pockets. It's currently asking $4.199 million.