14 Boutique Hotels Offer Authentic Stays in Chicago

As a Chicago-based company, we love to take any opportunity to brag about the city we call home. These Chicago boutique hotels capture the spirit of living in the Windy City and make it extra special, whether thanks to their proximity to the city’s most iconic landmarks, quality of the provisions, rooftop views, neighborhood ties, or—in most cases—some combination of all the above. These hotels exude the art of hospitality in every detail: beautiful spaces, neighborhood guides, topnotch service, and personal touches.

1. Longman & Eagle

Longman & Eagle offers a glimpse at Chicago’s history of drinking, with the inn as a classic spot to eat, drink, and stay overnight. The public space downstairs is centered around a dramatic bar and restaurant space—which can get pretty rowdy. If you are cool with spirited nights and their potential noise, the six bedrooms for lodging above are each well decorated and outfitted for a comfortable, contemporary stay. The establishment calls itself: “The sort of place where a man can get a shot with breakfast, where local politicians might trade votes for whiskey, and one that reflects Chicago’s unique neighborhood-based diversity.”

2. Chicago Athletic Association

Many a handshake deal has happened within the walls of The Chicago Athletic Association. Dating back to 1893, the Venetian Gothic landmark goes all in on Chicago history—and shares it with the public after 122 years of exclusivity. A collection of options for eats and drinks includes the gilded Circle Room Bar and Cindy’s rooftop bar—and a Topgolf Swing Suite and a Shake Shack. The sophisticated lodgings combine the elegance and athletic heritage of the building with contemporary amenities.

3. Hoxton

The Hoxton Chicago is located in Fulton Market, a district within the West Loop that has quickly become a hopping scene thanks to the boom of acclaimed restaurants and creative galleries in the formerly industrial neighborhood. With unfinished concrete ceilings, warehouse-style windows, paneled leather headboards, mid-century furniture, bedding by Chicago-based artist Cody Hudson, and artwork curated by local gallery Johalla Projects, The Hoxton is a bright, beautiful, inspired space to sleep, relax, work, and eat. The pool-adjacent rooftop restaurant, Cabra, is a delicious cevicheria from award-winning chef Stephanie Izard, but you’ll be surrounded by so many delicious food options in the West Loop that you won’t know where to go first.

4. Publishing House Bed and Breakfast

Before “Air” there were just ordinary B&Bs. The Publishing House Bed and Breakfast, however, is way beyond ordinary. 11 elevated rooms grant guests a private sanctuary, quiet and stylish. Located in the former Free Methodist Publishing House, built in 1909, the B&B came to be in 2017, giving the humble coziness of home a luxury twist. Of course, the other half of the establishment title is not to be ignored: Publishing House is known to serve a scrumptious morning meal.

5. Freehand Chicago

With rooms designed by Roman and Williams, Freehand Chicago offers comfortable beds and stylish spaces. With a mixture of private and shared rooms, the hotel group aims to combine the culture of a hostel with innovative design and tasty food and drinks. Each location takes a cue from its surroundings to reflect the city’s culture in its details to offer a sense of community in every space.

6. Thompson Chicago

The Gold Coast is one of Chicago’s most historically rich—and, historically, rich—neighborhoods. With its tree lined streets full of great restaurants and cute shops with the occasional manor by architect Louis Sullivan mixed in, the neighborhood is also home to the historic mansion that houses Thompson Chicago. Here, 247 luxury suites embody the grandeur of its surroundings, just a short walk from the beach and bustling River North. Some rooms even have floor to ceiling windows with a view of Lake Michigan and the city skyline.

7. The Robey

The Robey bottles up the spirit of Chicago in a refurbished 1929 Art Deco tower. On the corner of Damen, Milwaukee, and North Avenues, the building is situated in Wicker Park, northwest from Chicago’s downtown. The original building, designed by Perkens, Chatten, & Hammond, was refurbished by Belgian designers Nicolas Schutbroek Architects and Marc Merckx Interiors. The adjoining Hollander Fireproof Warehouse offers an additional series of Annex Loft rooms and a large hall, the industrial space finished with boutique touches and custom furniture by DELORDINAIRE architects. The hotel is famous even among locals for its rooftop bar. Sitting 13 floors high, the Up Room offers some of the best views of the city down the tree lined avenues.

8. Sable

Beneath the iconic Chicago Ferris wheel at Navy Pier sits the luxury boutique hotel Sable, whose branding and style was designed by the Gettys Group. Named for the aircraft carrier ship that was once docked at the pier, the hotel embraces the waves of Lake Michigan and the history of its location with blue, tidelike themes throughout the stunning rooms with incomparable views of the water. The restaurant Lírica offers Latin-inspired flavors, while Kisbi Coffee serves a mean cup of coffee. Upstairs, Offshore bar and restaurant grants visitors a large outdoor rooftop to enjoy cocktails and, in the summer, the firework show every Saturday.

9. Soho House

Soho House is always a reliable place to stay, especially if you’re already a member. The Chicago location is outfitted with a gorgeous pool deck, cafe, gym, and workspaces in addition to, of course, lodgings. 40 bedrooms in five sizes are available to members and nonmembers. A former belt factory, the 1908 Allis Building, the interiors reflect the industrial origins of the buildings and of the surroundings—the bustling Fulton Market District.

10. The Guesthouse Hotel

On Chicago’s north side, The Guesthouse Hotel is full of friendly vibes. Butting three welcoming neighborhoods brimming with local character, boutique shops, restaurants, breweries, and entertainment, the surroundings are particularly residential—it really does feel like a guesthouse. Outside the city center, the hotel offers suites to explore the city like a local. In addition to your own suite, Guesthouse has a Clubroom for relaxed reading by the fire and a Roof Deck for enjoying a beer in the sun. The spaces are each designed to feel personal and real—like a home away from home. But seriously.

11. Nobu Hotel

The art and food scene of the Fulton Market converge with the old-world Japanese and ultra-modern style of Nobu. Of course, the hotel offers more skyline views at The Rooftop, where chef Nobu Matsuhisa’s masterful menu is served in addition to downstairs at Nobu Restaurant. Outfitted with all the modern comforts and added amenities like a pool and fitness center, the rooms of Nobu Hotel are an oasis above the West Loop fray.

12. Hotel Zachary

A trip to Chicago isn’t really complete without a visit to the storied bricks and ivy of Wrigley Field. The 99-year-old stadium is a rock solid part of Chicago’s history and character, and Hotel Zachary gives you a taste of the action. With the stadium’s Chicago dogs within nose reach and home run cheers easily within earshot, the hotel is designed to combine history and style in a comfortable, modern space. The hotel, named for and modeled after the designs of Wrigley Field architect Zachary Taylor Davis, embraces the energy of Wrigleyville and channels it into more restful, artful spaces.

13. CitizenM

In the heart of Chicago’s downtown, CitizenM brings comfort and awe to Michigan Avenue. Stunning art curated by Floor Haverkamp makes the hotel an artistically enriching place to stay as much as a comfortable one. With a designer living room, tech-controlled bedrooms, and 24/7 food and drinks, and all the best amenities, the hotel makes both a stimulating and restful location to kick back after enjoying all the city has to offer.

14. The Emily

The Emily is a boutique hotel concept inspired by and named for 19th century artist Emily Carr, who used art to change the way we look at the world, specifically by depicting indigenous communities. The hotel aims to bring fresh experiences to the Fulton Market District with the hotel, coffee bar, rooftop bar serving small batch, family owned mezcals and tequilas, and the Rooftop Cinema Club, where a variety of films are screened for locals and visitors alike.