The Sophisticated Lady’ is the perfect choice for smaller size parties looking for charter boats in Chicago. Unlike certain types of charter boats in Chicago, ‘The Sophisticated Lady’ has ample space for you and your Chicago boat cruise. This gorgeous Chicago party boat can accommodate up to 49 passengers in luxurious comfort, and give you a tour of Lake Michigan with all the trimmings. ‘The Sophisticated Lady’ is the largest motor yacht of the charter boats in Chicago in the 49-passenger category.