Best hotels in Chicago 2023: Where to stay in the Windy City, from Downtown to Lake Michigan

The most American of all the big cities in the US, Chicago stands out not just for its ease of use (O’Hare airport is among the world’s busiest) or its eminently friendly locals (they call it “Midwest Nice”), but also for its stunning architecture. Walk among its 77 distinct neighbourhoods and you’ll find International Style skyscrapers, Frank Lloyd Wright-designed single-family homes, and everything in between.

Food is the big draw in this city of nearly 3 million souls, but if you’re looking for a killer place to spend the night, you can rest and digest in a former factory filled with tattooed hipsters or drop serious coin in a Magnificent Mile hotel.

Most first-timers to the Windy City (which some believe is named after politicians who were considered to be ‘full of wind’ in the late 1800s, rather than the extreme gusts peeling off Lake Michigan, Illinois) choose a room with a view of the water, but heading west affords more neighbourhood escapes where actual Chicagoans hang out. So, pick your poison, and bring comfortable walking shoes.

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The British chain makes its Midwest debut in Fulton Market, in a former warehouse where anyone off the street is welcome to hang in the double-height lobby for some free wifi and water. As such, the buzzy Hox has quickly become steep (and free) competition to Soho House across the street, and the go-to rendezvous spot for impromptu meetings and friendly gatherings. Each of the 182 guest rooms (Snug, Roomy and Cosy) draw inspiration from the building’s industrial past, with mid-century flair, and afford easy access to celebrity chef Stephanie Izard’s white-hot Cabra Cevicheria and the rooftop pool.

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What was once an exclusive men’s sporting club was reborn in 2015 as the coolest place to sit by a fire with a hot toddy or challenge a colleague to a darts match in the Games Room. The Chicago Athletic Association’s 240 sporty-chic rooms (note the gymnastic pommel horses at the foot of the beds), designed by Roman & Williams, take over most of the circa-1893 Venetian-Gothic pile, but there’s still plenty of space for seven bars and restaurants, including glassy Cindy’s rooftop restaurant, a mainstay in summer, overlooking Millennium and Grant Parks.

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Set across from the flagship Ralph Lauren and its ladies-who-lunch dining room, the landmark Park Hyatt – newly emerged from a $60m makeover – towers above the stretch of Michigan Avenue where out-of-towners come to spend their cash and locals befriend their personal shoppers. Try on your new Burberry trench or Gucci costume rings in an expansive suite with glorious views over Lake Michigan and the Water Tower. Don’t worry about overindulging and struggling to fit into that Row dress purchased at nearby Ikram; beloved NoMI has a semi-secret, six-seat sushi bar serving deliciously fresh fish by the piece or full eight-course omakase meals that won’t bust your belt.

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When diners arrive to indulge at lobby restaurant Adorn, they may do a double take. Gone are the clubby, dark interiors, refreshed with an open-plan, seventh-floor lobby/hangout called the Social Lounge and, at the back, a restaurant that feels like a living room, all designed by Rottet Studio. (The design team also did the meeting rooms and Presidential Suite.) After a dinner that starts with bread and edible candle, followed by lamb shoulder confit, head upstairs to one of the 345 sun-kissed rooms, which all come with views of the twinkling lights of the city or the ever-changing blues of Lake Michigan.

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Further west than one typically considers when choosing a Chicago hotel, The Robey has much to beckon visitors to the six-point intersection of Damen, Milwaukee and North Avenues. The Art Deco building, for one, captures the storied spirit of Chicago; it’s the only skyscraper for miles, and stretches 203ft, so the views are spectacular in every direction. Then there’s the rooftop experiences, starting with a sixth-floor pool and deck, the raucous Cabana Club (try a frozen cocktail), and the hard-to-get-into Up Room on the 13th floor (guests get preferential reservations). Come for the people-watching, stay for the cosy rooms.

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This urban resort rises 18 storeys and also boasts one of the city’s prized rooftop pools: summer weekends often find “overserved” brunch diners in their linen finest falling into the water. This prime location, right above what Chicagoans affectionately call the Viagra Triangle, overlooks the best restaurants and shopping through floor-to-ceiling windows – not to mention sweeping views of Lake Michigan and the cityscape beyond. Definitely book a meal at Somerset on the ground floor, which spills onto the vibrant sidewalk, then take a lounger at the rooftop bar and watch the city’s beautiful people in action.

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Taking over the 1929 Art Deco Carbide & Carbon building just south of the river in the Loop business district, the burgeoning chain hotel actually did a stunning job with its new Michigan Avenue outpost. The building itself is all dark green and gold, supposedly mimicking the shape and shade of a Champagne bottle (a wink to Prohibition Era rules and the shenanigans that undoubtedly went on behind closed doors here). Rooms are handsomely outfitted in black and white, with splashes of red lacquer here or teal velvet there – very glam. A sun-drenched rooftop restaurant and bar offers sweeping views of the buildings on and around Michigan Avenue, while the ground-floor lobby’s library vibe and hidden five-seat bar are a throwback to the Roaring 1920s.

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Considered by many to be the best Peninsula in the world, service here is as personal as the rooms are high-tech. Change the music or the lighting, or call your butler with a touch of a button, though in all likelihood, he or she already knows to bring you an espresso and have your suit pressed (this is where all the boldface names stay when they’re in town for a gala). In keeping with its Asian roots, the opulent 331-room hotel has the best Chinese restaurant in town, the Shanghai Terrace, and keeps privacy paramount. Still, don’t be surprised to run into a basketball star in the lobby or an A-list Hollywood producer in the indoor pool. Just remember to play it cool.

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From the moment you step into the Mies Van der Rohe building, walk past the Jaume Plensa marble sculpture, and up to the 12th-floor lobby hung with glass pebbles, you know you’ve entered a spiritual space. Austere it may at first seem, the 316-key hotel is rife with whimsy: in the children’s play room, in the private cinema (first come, first served, always free), and in the playful flavours on the menu at Travelle, the hotel’s award-winning restaurant. Some 140 pieces of art brighten the light-filled building (you can even take a guided tour), while the Chuan Spa provides the ultimate pampering reprieve from the Windy City winters – and is anything but ascetic.

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Lunch is a big deal at the Thompson – its Nico Osteria is one of the few places to offer it in these parts – but then again, so are weekend brunches, where sharp-dressed locals linger for hours over bruschetta and prosecco. Upstairs is quite a scene, too, with 247 rooms dressed in masculine greys, blues and browns that echo the skyline and the Lake. The amenities are few (there’s no spa or pool), but it’s still a Chicago favourite for its darkly cool atmosphere and thoughtfully chosen art collection (nip into the four-storey secret stairway for a peek at the works of some of Chicago’s revered graffiti and street artists). The smart money use the Thompson for romantic staycations: start an evening drinking and dining at the bar – who knows who you might run into? – then sleep off the night before in one of the plush guest rooms.

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The Sophy was the first boutique hotel to hit swanky Hyde Park, but quickly became the social hub for Southsiders. Along with 98 guest rooms (many with custom artwork and turntables with curated vinyl) and an unbeatable location on the buzziest section of South 53rd Street, the hotel offers a thumping lobby bar that gives a nod to the Nobel laureates who taught at nearby University of Chicago, and a restaurant, The Mesler, decorated with book jackets by notable Chicago authors. Mingle with poets, artists, foodies, politicians, scholars, musicians, and anyone who’s anyone in this industrial-style building inspired by Frank Lloyd Wright’s nearby Robey House.

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The newest addition to a growing collection that now includes some 26 properties, from Shoreditch to São Paulo, landed in perhaps the buzziest part of town. Nobu Chicago’s brick-and-steel exterior blends seamlessly into the industrial facades of the West Loop, while, inside, the 115 rooms and 23 suites deliver a Zen-like vibe with a clear Japanese POV. Obviously, guests can’t resist dining at Nobu (it is, delightfully, the same menu and quality as other Nobus the world over), but they also can’t skip taking a soak in a teak oforu tub (the suites have them; and they are worth the extra cash) or walking down the moody halls, lit with Japanese lanterns, to the indoor tranquility pool, lined with daybeds and illuminated by a wall of cascading pink resin leaves. Don’t miss brunch, where Chicago’s best-dressed come at the weekends after morning yoga.

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The former Ace Hotel kept its youth-culture bona fides while transitioning to appeal to a slightly less tech-bro regular. Named after 19th-century artist Emily Carr, the 159-room hotel draws locals who would rather work from this art-studded lobby than their tiny apartments; anyone keen to interact with the rotating artists in residence; and film junkies who rock up to the Rooftop Cinema Club (during warmer months) to watch cult classics (Coraline, Candyman) playing on a giant LED screen (noise-cancelling headphones included) on a grassy fifth-floor deck. Opt for a Love Seat + Popcorn for two ($27.75) and order dinner from the new Mexican-French concept restaurants, Fora. Come early for classic Midwest games, such as cornhole, and bring a blanket from your industrial-functional guest room (it gets cold on the roof).

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Locals will tell you that no real Chicagoan goes to Navy Pier, a 50-acre extension of the city with a museum, restaurants, shops, outdoor venues, the launching pad for high-speed lake excursions and, of course, a Ferris wheel (the first one was premiered in Chicago). But, of course, Chicagoans do end up at this “municipal pier” – which was part of the original 1909 Plan of Chicago – whether it’s to see Chicago Shakespeare, the annual art-focused autumn Expo or summer’s fireworks and the epic Air & Water Show. Now they can spend the night at the newly opened Sable at Navy Pier, which houses generously proportioned guest rooms with floor-to-ceiling views of the city and lake, but also the nation’s largest rooftop deck, Offshore. It’s all the way out there on the water, which makes it feel like a real escape.

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