Known for its stunning mix of modernist, gothic, and neoclassical styles, Chicago‘s architectural DNA extends from beyond the downtown skyline. In fact, you don’t have to venture far from many Airbnbs in Chicago to get a front-row ticket to the area’s astounding design. Whether you’re looking to stay downtown—in one of the many eccentric neighborhoods—or on a quiet residential street, there’s something for everyone. From an old factory turned industrial loft with towering ceilings, to an original Frank Lloyd Wright prairie home in Rogers Park, to a gothic-inspired condo outfitted with dark and moody decor, these unique properties all give you a taste of the Windy City’s famed architecture. Additionally, they position you near some of the most iconic landmarks, including the riverfront, Magnificent Mile, must-see beaches along Lake Michigan, Lincoln Park, and the vibrant restaurants and bars of the West Loop. While the city is home to some gorgeous (and affordable) hotels as well, these Airbnbs provide a bit more of a unique stay for groups of all sizes and needs.
Note, many of these properties book up fast—so don’t wait! Here are the best Airbnbs in Chicago right now.
While we have not stayed in every Airbnb featured, unless otherwise stated, these listings are vetted based on Superhost status, amenities, location, previous guest reviews, and decor. This gallery has been updated with new information since its original publish date.
