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This hotel is on our list of The 11 Best Hotels in Chicago.

Set directly across from the Art Institute of Chicago, this former members-only men’s gymnasium is now the Chicago Athletic Association, which is part of Hyatt’s Unbound Collection. Enter at street level off Michigan Avenue and walk toward the back to find a staircase that leads to the old swimming pool, now a venue for parties and pop-up concepts. Take the nearby elevator to the restaurant, Cindy’s, easily the best rooftop scene in the city, with highly Instagrammable terrace views overlooking Millennium Park, the swooping Frank Gehry–designed bandshell, and Anish Kapoor’s Cloud Gate (aka the Bean).

Park yourself in the second-floor lobby and hang with locals as they tap away on their laptops and sip lattes by the two oversize fireplaces. Walk through that expansive by Roman & Williams–designed room, where light beams in through ornate stained-glass windows, and you enter a warren of table games and darts, all festive and typically open to the public. There’s also the secret six-seat bar, the Milk Room, a relic of Prohibition, and the James Beard Award–winning Cherry Circle Room—a sexy, dark restaurant with a circulating martini cart and a meat-centric menu.

Upstairs in the 1893 landmark, 240 guest rooms reflect the building’s former life, with gym horses as foot beds, working fireplaces in some rooms, plasterwork ceilings, ornate carved wood wainscotting, and a clubby vibe. Some of the rooms are rather small, but the location is hard to beat, and the cozy, wintry ambiance makes it a popular (and fun) place to spend a weekend. And because the CAA keeps an eye on its water conservation, sources its food locally, and adheres to strict recycling standards, eco-conscious travelers can feel good sleeping here.

This hotel is on our list of The 11 Best Hotels in Chicago.

Following a much-needed $60 million makeover in July 2022, the Park Hyatt Chicago is once again a contender for one of the best hotels in town. Located in the bustling Magnificent Mile neighborhood at 800 N. Michigan Avenue, the storied property has been a landmark destination since it opened in 1980 as the first property to bear the Park designation. The renewed sanctuary now delivers a true sense of place, with a refreshed lobby design that’s more of an urban living room, an updated Library, and a vibrant new art program spotlighting some of Chicago’s most talented creatives. Critically, the hotel’s signature restaurant NoMI (named for the location on North Michigan Avenue) now has three different concepts: NoMI Kitchen, which emphasizes American cuisine with French techniques, NoMI Garden, a terrace space that’s ideal for lunch, and NoMI Lounge, which includes a six-seat sushi bar.

The Park Hyatt Chicago, facing ever stiffer competition from newer luxury hotel entries in the Magnificent Mile orbit, nevertheless remains a great choice for families because of the central location optimizing sightseeing and kid-heaven treats. Budding geologists will love the geodes, minerals, and marine fossils in the lobby alcove. Chefs at the seventh-floor NoMI restaurant, known for fine wines, city views, and standout American contemporary cuisine, take young foodies to the open kitchen’s soft-serve ice cream dispenser. The 7,000 square foot fitness center includes a 25 yard lap pool with skyline views, or borrow a complimentary Jamis commuter bike to ride the scenic Lakefront Trail four blocks east on the beach side of Lake Shore Drive. Guestrooms have notable design flourishes such as padded window seats, Eames chairs, and Mies van der Rohe–designed Brno desks from which to view the city’s famous architecture. Pets are welcome, and the hotel donates 100% of its standard pet fee to one of the city’s largest animal shelters.

A recent makeover of the Four Seasons Hotel Chicago from Houston-based Rottet Studio did away with the dark and clubby vibe common in older Chicago hotels in favor of a brighter natural palette. Today, the lobby is open and bedecked in oversize floral arrangements; the open-plan lounge there, with its modern glass chandelier, has become a high-end local watering hole known as the Social Bar. The new Adorn restaurant is now a big-night-out dining destination courtesy of chef Richie Farina’s creations that range from a perfectly prepared filet mignon to caviar and eggs. Upstairs, the 345 guest rooms—more than half are suites—feature understated grays and pale greens and come with deep soaking tubs and (if you ask) unimpeded views of Lake Michigan.

Down a side street not far from MoTown Museum and the Wayne State University’s main campus is one of the city’s hidden art gems. Lincoln Street Art Park is an evolving community collaboration between local artists, the Michigan Council for Arts and Cultural Affairs, the Detroit Recreation department, and the adjacent recycling center. Visiting the outdoor site, particularly on a sunny day, is akin to walking into the rugged studio of an artist, complete with seating area, mini library, and house pet. In this case, a giant dinosaur twice the size of an average loft’s ceiling, but reminiscent of a pet nonetheless. I explored the park alone, but I think it would be a wonderful place to visit for a couple on a date and a really good option for kids to roam and explore at leisure. The outdoor exhibit is open rain or shine, 24 hours a day, seven days a week, 365 days a year and is free to the general public. The park is located at 5926 Lincoln Street, Detroit, Michigan 48208.

The Chamber Music Society of Detroit plays at a revolving list of nine venues in Southeast Michigan during a series of events throughout the year, such as the Sunday Recital Series, Signature Chamber Series, Listen at the Library, and CMSD in Depth. Fans of classical music should not miss the chance to catch a performance of this world-class group that has been performing since 1945.

On the first Friday of each month, Cranbrook’s Science Institute is open free after 5:00 p.m. It’s a chance to roam with dinosaurs, gaze at stars through powerful telescopes, chill out in the ice age exhibit, learn more about the history and cultures of American Indian peoples, dig into anthropology, study minerals, and better understand water—amongst a few other things! It’s a diverse collection of learning experiences unlike any other place in Michigan. It’s remarkably hands on, and, while targeted at children, incredibly fun for adults as well.

It’s not often one gets to visit a home designed by legendary architect Frank Lloyd Wright—much less stay in one—but the Palmer House lets you do both. Situated in the nearby city of Ann Arbor, home to the University of Michigan, the brick and cypress home is one of Wright’s last masterpieces and features a teahouse on premises. Guests can rent the three-bedroom house for a quick getaway or for an event (25 people max for the latter).

This purpose-built luxury high-rise hotel has 400 rooms in all, with natural light spilling through floor-to-ceiling windows onto modern, clean-lined furnishings done in ivory and gray tones. Higher floors offer spectacular views of Lake Michigan and Navy Pier. Service here gets high marks for the nothing-is-impossible attitude of the staff, and from early summer to late fall the Streeterville Social, the third-floor roof top outdoor terrace, offers craft cocktails and relaxed dining… and views of the city skyline.

Hungry travelers have a few options, including the hotel’s signature modern French brasserie and café, Venteux, but the real action is upstairs at the French-inspired rooftop, Château Carbide. Set in what would be the cork of this (literally) gilded bottle-shaped tower, the secret plein-air space had never been open to the public until 2021; in June 2023, it was reimagined as an absinthe bar, where the plant-based liquor takes center stage on the cocktail menu, with spectacular city views as the background.

The Cranbrook Educational Community is one of the most revered names in Michigan, and under the umbrella of that name is an art museum, a secondary school, a graduate program, the institute of science, a research center, and historic homes with extensive gardens. The Cranbrook Art Museum was one of the earliest institutions in the U.S. to feature contemporary art. A few of the more recent exhibitions have included the works of George Nelson, the Italian design factory Alessi, and Danish ceramist Anders Ruhwald. There is also an annual graduate students’ art show. Even the building that houses the esteemed museum is worth a visit, with its mixture of neoclassical, art deco, and contemporary architectural details.

Rocky’s has been in business in Detroit since 1969. In its current form on Russell Street in the Eastern Market neighborhood, it’s a superstore for candy and nuts. However, it also offers spices, oils, specialty cooking items like gluten-free flours and mixes as well as ‘Made in Michigan’ products, such as McClure’s Pickles. Most items are only available in bulk. Some items are pre-packaged. Take your time exploring the aisles, Rocky’s is not small and hidden gems abound in its many aisles. It’s an ideal place to take the kids but travelers of all ages will find something to love. Products can also be ordered online and shipped to your home.

This hotel has changed ownership and is now the Ambassador Chicago.

In 2011, hotelier Ian Schrager reopened the iconic but faded Ambassador East Hotel as the Public, instantly infusing Chicago‘s Gold Coast with some flash. Its Pump Room restaurant was the city’s first posh, post-Prohibition, celebrity hangout (everyone from Fred Astaire to John Belushi has come). Keeping its name but little of the old decor, the revitalized Pump Room has a 24-foot bar with a 12-karat white gold–leaf ceiling and a changing menu by Jean-Georges Vongerichten. The high-ceilinged, columned lobby feels both grand and intimate, and it’s now divided into a lounge with a computer-equipped workstation and an elegant library/coffee bar with deep couches and original art, including photos by Hendrik Kersten. Residential high-rises along Lake Shore Drive obscure views of Lake Michigan from the hotel, but drop-dead gorgeous rooms elegantly infuse the pre-WWII architecture with white stuffed couches, bronze textiles, and white sheepskin throws for an effect of lush minimalism befitting one of the city’s oldest and toniest neighborhoods.

“Have you heard about d’Mongo’s? It is Ryan Gosling’s favorite place to visit when he comes to town!” Although I never saw Ryan Gosling, bartender Red knew immediately that I was new in Detroit and that I’d never been in before. She recommended I try the Detroit Brown, made with Michigan’s own ginger ale: Vernors. As I sipped gently from the cold glass and looked over the top of its rim at the eclectic crowd filling the speakeasy, I couldn’t help but think, “Who cares what celebrity does or doesn’t frequent this place, I’d come back here for the drinks and the crowd any day!” Cafe d’Mongo’s draws a crowd every night it is open—which is usually only on Friday, maybe Saturday—and whether the customers come because of the drinks, the music, the crowd, or because they hope to see Ryan Gosling or Mark Wahlberg, the point is they keep coming. There’s an element of secrecy that has kept even my hotel’s valet from being able to tell me how to get to the revered speakeasy, yet it’s one of the first places I heard about when I asked people on the street where I needed to go get a drink in Detroit. If you find yourself at Cafe d’Mongo’s, tell Red I say hello, and order the Detroit Brown.

Behold a pizza place worth the wait—Buddy’s Pizza is praised for its take on Detroit-style pizza: a square-shaped, deep-dish pie topped with marinara, and cooked to chewy perfection. Health-watchers rejoice—their pizza also comes gluten-free. With recognitions such as “Nation’s Five Best Pizza Places” from the Food Network, this restaurant is one that cannot be missed.

With just over a year in business, Green Dot Stables is still new, but owner Jacques and his wife took over a building in Corktown that isn’t. Instead, they took it from abandoned and historical to historical but fresh. The interior still retains its ode to horse racing and is kitschy appeal without being cheesy. An innovative new menu presided over by Les Molnar features more than 20 unusual and classic sliders with a “mystery meat” option that changes often. On the day I visited, the special was Lamb Tongue with Dijon Brown Butter and Fennel Relish. My favorite was the Corned Beef Slider with Wigley’s-Brinery Kraut, Pickle and Mustard Aioli. Local and imported beers anchor the drink list and their soda (or pop as it is known in the Midwest) is mixed in-house with locally made syrup. Optional sides include truffle fries, poutine, chicken and orzo salad, kale & quinoa, or classic mac ‘n’ cheese. Menus items start at an affordable $2 and it is a packed house during the lunch rush so plan accordingly or visit at odd hours to ensure fast service.