21 Best Chicago Airbnbs for Your Next Windy City Trip (2022)

If you’re looking for the best Chicago Airbnbs, you’ve come to the right place. We’re big fans of the Windy City, and why wouldn’t we be? It’s got a vibrant art scene, skyline views around every corner, an unparalleled restaurant and bar roster, and enough cultural attractions to easily fill several itineraries.

With eye-catching architecture, plenty of attractions within walking distance of the central neighborhoods, and a diverse landscape, Chicago brings forth a hustle and bustle exclusive to its borders. Whether you’re hoping to catch a Cubs game or roam an array of museums, lots of adventures await. And if you thought the tourist attractions ended there, think again. During your getaway, you can even make a pit stop at one of the many jaw-dropping beaches lining Lake Michigan. Ahead, discover the very best Chicago Airbnbs and the perks that come with them.