While massive hotel chains aren't for everyone, Chicago boasts some of the best hotels, which you should totally check out. Thankfully, the Windy City has an impressive assortment of boutique properties that trade size for warm, personalized service and a huge helping of character. And these are things we certainly look for in our hotels here at Time Out.
Whether it's your first time here or you're planning a cheeky staycation, these boutique hotels make a cozy backdrop when you're away from home. Our top picks range from a stylish stunner in Wicker Park to a British import crowned by one of the city’s best rooftop pools. With choices like these, you'll be packing your bags in no time. Happy vacations, people. Or maybe even a staycation? Because any excuse to stay in some of these...
Find more places to stay with our guide to the best downtown Chicago hotels in the Loop. Or stay one of the coziest Airbnbs near Chicago this winter. Feeling fancy? Check out the most lavish Airbnbs in Chicago. Feeling quirky? Here's the most unique Chicago Airbnbs.
Who makes the cut? While we might not stay in every hotel featured, we've based our list on top reviews, hosts and amenities to find you the best stays. This article includes affiliate links. These links have no influence on our editorial content. For more information, see our affiliate guidelines.