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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.

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.

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.

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

Chicago invented the skyscraper, and some of the world’s most elegant examples define the city’s skyline. You can stay in the coolest one of them all, designed by German American architect Mies van der Rohe and run by Langham Hotels. To access the Langham Chicago’s minimalist-yet-opulent 268 guest rooms (including 48 suites), you must first check in at the second-floor lobby; its ceiling is hung with silver pebbles, its sofas populated by stylish guests, and its David Rockwell–designed Travelle restaurant alive with music and bites by executive chef Damion Henry during coveted afternoon teas.

The former IBM building with a black exoskeleton also houses a Chuan Spa, which specializes in such Eastern therapies as acupuncture, cupping, and gua sha. A 67-foot-long indoor pool and full-service fitness center are available to all guests.

Anyone spending the night in the rooms, with floor-to-ceiling glass windows framing Chicago views, has access to one of the city’s best concierges, who can organize a River North food tour, a Frank Lloyd Wright walking excursion, or a mixology class at Travelle. Don’t leave without taking a photo beside Jaume Plensa’s “Anna” sculpture in the Wacker Street lobby—then walk over to Millennium Park to see his larger works on display.

Find well-being with style in this dreamy beach destination.

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

The world has been waiting years for the St. Regis Chicago, located in the city’s 101-floor skyscraper designed by Jeanne Gang, to welcome guests and owners; in 2023, it finally made its stunning debut. The triple-tower building’s architecture was based on the frustrum shape, which is basically a pyramid with its top chopped off. (Think of a popcorn box.) That form is replicated subtly throughout the hotel, from the exoskeleton to the marble tiles in the inviting lobby on the Chicago River. Each of the 192 guest rooms comes with floor-to-ceiling windows and panoramic city views, a dedicated butler, one of four soaking tubs, brass detailing, and curvilinear furnishings from a collaboration between architectural powerhouse Gensler and boutique firm Simeone Deary Design Group.


Rounding out the amenities: the Miru all-day-dining restaurant that is anything but casual, a new Tuscan steakhouse concept, a truly cossetting seven-room spa, an indoor pool with an outdoor patio, and the finest urban hotel gym probably anywhere. Was the wait worth it? Indeed it was.

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