6 Best Hotels in Chicago, Illinois

Directly across from Lincoln Park, this historic property has a cool, kitschy vibe but still feels authentic, thanks to details like the original Hotel Lincoln sign in the lobby. Its guest rooms also combine vintage and modern elements, including original art; for the best views, ask for one on the ninth floor or above, facing east toward the park and the lake. Take in some of the city's best views over cocktails at the J. Parker rooftop lounge or grab a bite---dining options range from locally made pastries at casual Elaine’s Coffee Call to approachable American fare at the sleek Kennison restaurant to lavish 17-course feasts at Sushi Suite 202, an omakase “speakeasy” secreted inside a converted guest room.

The restaurant known for whiskey and nose-to-tail cuisine has opened a six-room inn by the same name, and each of these homey quarters is full of original art and handcrafted furnishings. No room has the same look and feel, but each is residentially styled to appeal to the young travelers who stay here to be in the middle of a cool neighborhood scene. Comfortable and welcoming, it's like crashing at your (very tidy and organized) best friend's pad.

Far from just a generic amenity, the fitness facilities are the raison d’être at this independently owned Bucktown property; after all, it got its start as a tennis club that’s hosted the likes of Billie Jean King and Venus Williams (who kindly pitched in and designed a lounge when the club was overhauled and the hotel added in 2017). The multistory facilities and class offerings are impressive---think sunrise rooftop yoga and spinning, a heavy bag boxing gym, two sleek pools, and a virtual driving range, to name but a few---and the coolest feature is that they’re all open to hotel guests for no additional charge. (Spa treatments and personal training sessions not included.) Throw impressive skyline views and, oh yeah, slick mid-century guest rooms into the mix, and you’ve got a seriously unique spot to rest your head.

The friendly proprietors (and longtime Bucktown denizens) launched this guesthouse, at the end of a residential street, in 2021 after lovingly restoring its three guest rooms with a mix of crisp modern style and cozy touches like butter-soft linens and Aesop bath products. Cool graphic posters from the annual Bucktown Arts Fest (which the owners help run) add local color to the hallways. There’s a small shared kitchenette, but if you prefer to let someone else do the cooking, the property’s ground-floor tavern serves a smash burger that’s wildly popular with the neighbors.

This Tuscan-theme bed-and-breakfast—complete with a (shared) fully stocked gourmet kitchen—allows guests all the comforts of a top-notch hotel in a residential neighborhood where such rooms can be hard to find. The common area is small but well appointed; mahogany floors and columns, silk couches, plus an enormous hand-carved banister add a regal touch. The bathrooms, with floor-to-ceiling marble, are spacious and decadent. Be sure to visit the grotto out back; the bricks are from Italy.

One of the condo-like rooms in this small B&B is a great choice for anyone who wants to venture outside downtown Chicago and sample two of its most popular neighborhoods—Wicker Park and Bucktown. Each room is unique; all are tastefully decorated with streetscape photography, handmade beds, and hardwood floors, and some feature original fireplaces. A stylish shared kitchen serves as the main hangout space. This is a great place for a long stay.