In the Windy City, the best Chicago Airbnbs are prime examples of how art, architecture, and history can converge in one space, whether you choose to spend your vacation in a moody, speakeasy-inspired pad in Avondale or a luxury penthouse on the Gold Coast. Just as each property in Chicago’s gridded city streets contains multitudes, so do its 77 diverse neighborhoods themselves, from the Michelin-starred restaurants that dot the West Loop and Lincoln Park to the art havens of Pilsen or West Town.