If you’re interested in exploring the breadth and depth of Chicago’s renowned architecture, there’s a good chance you can start in your Airbnb. For a city that’s known the world over for its eclectic collection of modernist meets gothic meets neoclassical, many examples of the Windy City’s historic cityscape lie outside the downtown corridor. From industrial lofts with soaring ceilings in the West Loop to a restored prairie-style home built by Frank Lylod Wright or bright and airy condos in Oak Park, these Airbnbs offer a taste of what makes this city so spectacular. Use them as your home base for some of the city’s best activities: an architecture boat tour along the Chicago river, a bustling food and bar scene, and an inspired art scene, plus the must-visit beaches along Lake Michigan.
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.
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