Photo-Illustration: The Strategist; Photos: Chicago Athletic Association Hotel, Getty, Joshua Haines, Allison Ziemba,
For those heading to Chicago — be it for a conference, a wedding, a ball game, or just a change of scenery — navigating where to stay involves triangulating a few factors. Do you want to be within walking distance to buzzy new restaurants? You probably want to stay in the West Loop. Feel like relying solely on the el train? Look for a place downtown near the Loop. In the mood for urban beaches, a lush park, and a zoo? Try the Gold Coast and Lincoln Park. (And a visit during spring or summer.) From there, do you want a view of Lake Michigan and a bathroom with spa lighting, or access to a co-working space? Room-service ice cream sundaes, or vintage kilim rugs?
Though Chicago winters are notoriously relentless, this is also when airfare and hotel rates drop and dinner reservations become easier to score. Make it work with a heavyweight parka (temperatures hover around 30 degrees during the day) and by staying central. (The Loop is near the Art Institute and Anish Kapoor’s oft-Instagrammed Bean; the West Loop has Girl & the Goat, the Publican, and Monteverde.) Or just go in the summer, when the city livens up and you can swim in the lake and catch a Cubs game, but not hypothermia. To figure out where to stay in Chicago, regardless of occasion or season, we asked 16 stylish travelers — from restaurateurs to photographers and designers — about their favorite accommodations. Here’s what they recommend, from the revamped athletic club to the contemporary room above a tavern.
Right off Chicago’s Magnificent Mile is the Peninsula, which came in as the favorite for three of the people we surveyed: interior designer Nate Berkus, Vosges Haut-Chocolat owner Katrina Markoff, and co-founder of the Hao Life remedy line William Li. This is where you go when you don’t want to skimp on luxury, where the beds are best-sleep-of-your-life good, and the minibar has Bernardaud china. Berkus notes the Peninsula’s “immaculate service and great spa,” which is considered one of the city’s best, although the huge marble bathrooms in guest rooms are practically spas in and of themselves: They come equipped with a bathtub “spa button” that softens the lighting, streams in a soundtrack, and activates the Do Not Disturb sign on the door. Markoff, a Chicago local, says she loves the rooftop Z Bar. “The city views and the vibe is all Chicago,” she says. “My favorite cocktail is the Cherry Blossom, made with sakura preserves.” Li says the food at Shanghai Terrace, which serves Cantonese dishes in a 1930s supper-club atmosphere, is some of the best Chinese food he’s ever had. “I always hunt for the best Chinese in every city I visit. And in Chicago, it’s at the Peninsula.”
Fitness and travel blogger Kira West loves Nobu Hotel Chicago for its location — in Fulton Market, walking distance from restaurants like Au Cheval and Little Goat Chicago — paired with its tranquil vibes. Upon arrival, Nobu’s guests are presented with oshibori, the Japanese tradition of offering steamed hot towels, and led to minimalist guest rooms decked out in blonde-wood wainscoting and floor-to-ceiling windows. West says the 40-foot indoor tranquility pool, steam rooms, and gym are worth a visit, but that the real highlight is the in-room teak soaking tub — so make sure to book a room with one. Downstairs, there are a few options for experiencing the hotel’s namesake chef Nobu Matsuhisa’s cuisine: The hideaway bar on the mezzanine, the ground-floor restaurant, and the 11th-floor skyline-framing rooftop are all spots where you can order yellowtail jalapeño sashimi and Japanese old-fashioneds.
Photo: CHRISTIAN HORAN PHOTOGRAPHY/CHRISTIAN HORAN PHOTOGRAPHY
Jewelry designer Ippolita Rostagno recently opened her second Ippolita store in Chicago, at 900 North Michigan, and says she stayed at the Four Seasons for every visit. “The location” — on the Magnificent Mile, near Lake Michigan and the Museum of Contemporary Art — “makes it the ideal place when traveling to Chicago for just a few days.” Besides the friendly staff and terrific service, which Rostagno says are the best around, the hotel’s concierge offers a menu of personalized events: architectural tours as well as private, in-room cooking demos with James Beard Award–winning chef Jonathon Sawyer, or a guided tour of the hotel’s art collection, which includes contemporary works by Dawoud Bey and Tomás Saraceno, followed by a custom tasting menu inspired by the art. As for the actual rooms, Rostagno recommends booking a lake-view room for looking out over Lake Michigan, as well as the pages-long in-room dining menu, which includes over-the-top items like ice cream sundaes, made on the spot, and “Mojitos and Manicures.”
“Every time I’m in Chicago, no matter how short or how long, I stay at the Chicago Athletic Association Hotel,” says Alfredo Paredes, founder of his eponymous design studio. Roman and Williams renovated the 1893 Gothic-style building, which is in the Loop but right by Millennium Park, in 2015, updating its history as a private sporting club for the city’s upper class. Roman and Williams kept original details, like the grandiose façade, stained-glass windows, marble staircases, and carved-wood fireplaces, while adding new fun touches like pommel horse benches, pull-up bars, and boxing-style sweatshirt robes. Book a room on a higher floor for the view, advises Paredes, and make reservations for both the hotel’s glass rooftop viewing atrium, Cindy’s, and eight-seat speakeasy, Milk Room.
Lance Lawson and Jim Wetzel are co-owners of the Chicago concept store Space 519 and say the Langham is where they book all the designers who come to town to make store appearances. “You have a front-row seat to the world-class architecture that made our city famous,” Lawson says. “We think it shows off the very best of our city.” Located on the riverfront in downtown Chicago, the hotel occupies the first 13 floors of a bronze-and-glass tower, the last by Mies van der Rohe. Guest rooms come with custom mini-cellarettes (small, portable wine coolers) and abundant floor-to-ceiling windows that “create postcard views of Chicago,” Lawson says. Lawson and Wetzel also love the Langham’s distinctly English sensibility. “Every time we walk through the entrance, we feel like we’re in London,” Wetzel says, noting the afternoon tea and classically uniformed bellhops. For those interested in getting a meal on the premises, Lawson recommends posting up at the bar at Travelle. “It’s a terrific mix of local creative and business types, as well as tourists from all over the world,” he says.
Stylist Mieke ten Have always books a room at the Viceroy when photo shoots and projects take her to Chicago. Located in the tony Gold Coast neighborhood, the hotel is a ten-minute walk from Oak Street Beach and a brief stroll from Magnificent Mile. Once the site of the 1920s-era Cedar Hotel, the Viceroy revamped the landmarked Art Deco building in 2017, adding metallic wallpaper, lacquered wood finishes, mirrored surfaces, brass light fixtures, and curvy velvet and leather sofas. A neon sign from the original Cedar Hotel is a retro reminder of the building’s past. There’s a full gym, rooftop pool, and two on-site dining options: the all-day restaurant Somerset and the Devereaux bar, which comes with views of the skyline. But it’s the swanky rooms that most appeal to ten Have. “It’s like a mini-holiday even though I’m there for work,” she says. “The bathtub is the perfect size and I fill it with their bubble bath. Then I order dinner from the restaurant downstairs and eat it in bed with a demi bottle of red wine. This is my routine; so many hotels don’t have bathtubs anymore, so I always prioritize that when I book.”
When restaurateur Yann de Rochefort visits his Boqueria outpost in Fulton Market, he checks in at Soho House Chicago just two blocks away. This location, like most of Soho House’s, is available only to members. (Membership starts at $2,400 per year.) “I feel at home the moment I step in the front doors,” de Rochefort says. Built in a former belt factory in 2014, this location’s expansive ground-floor lobby is open to the public and includes a coffee shop and bar. Besides the industrial, lofty rooms, members get access to a private screening room, clad with red velvet armchairs, a rooftop deck with a heated, 80-foot pool, and the Cowshed spa. Also reserved for members is the gym, fully equipped with a professional boxing ring with leather ropes — de Rochefort’s favorite amenity. “It’s high-design and nostalgic, but totally functional. A great place to work up a sweat,” he says.
Interior designer Kate Towill recommends the Hoxton. “It’s newish and located in the West Loop, which is basically Mecca for food lovers,” she says. Open as of 2019, the property marks the third Stateside location for the London-based hotel group, which caters to travelers more interested in location and a happening lobby than big, luxurious rooms. The lobby here is especially a draw, says Kevin Osterhaus, president of Graduate Hotels. A bit brighter and more pastel than the well-known Ace lobbies, this two-story space is filled with abundant seating, communal tables, loads of green plants, and a coffee bar. For remote workers who need a step up from that, the Hoxton’s flexible co-working concept, called Working From_, offers studio spaces, desks, and day passes, along with storage lockers and bottomless cups of tea and coffee.
As the New York–based creative director of Chicago-based furniture line Interior Define, Benjamin Reynaert heads to the Midwest once a month for work. “I prefer staying at the Robey, purely for aesthetic reasons,” he says. Originally built in 1929 as an Art Deco office building, the Wicker Park hotel opened as such in 2016. “The views of downtown are spectacular, especially from the Up Room, which is the rooftop bar and lounge,” says Reynaert, who recommends its Negroni. The lofty rooms are treated with streamlined mid-century furnishings (sleek task lamps, curvy leather armchairs, pared-down wooden tables) and industrial finishes like washed concrete walls and exposed-bulb lighting. The Robey also offers more room configurations than most hotels: Guests can stay in a room with a king bed, or can bunk up with friends or kids by booking a room with a queen and lofted twin or bunk beds.
Photo: Clayton Hauck
“Most people know Longman & Eagle as a mainstay bar and restaurant in Logan Square, but few are aware there are six rooms available upstairs,” says mixologist and author Maxwell Britten. The Michelin-starred restaurant opened in 2010 and added a set of guest rooms a year later as an homage to the no-frills pubs and inns of Chicago’s past. The rooms are small, but feel very much like someone’s well-appointed apartment with exposed-brick walls, hanging terrariums, and goodies like vintage cassette players with curated mixtapes, dog-eared books, indie magazines, and soap and shampoo from Aesop. Plus, Britten says, “You aren’t looking out the window of a high-rise,” but rather out onto a “street in a culturally rich neighborhood.” While the Inn offers a disclaimer that its rooms “are above an occasionally raucous, whiskey-fueled tavern,” the upside is that 150 varieties of whiskey and some of the best food in town are just downstairs — Britten suggests making a dinner reservation when you book your stay.
Chicago local Katrina Bravo prefers the home-away-from-home vibe of the Publishing House, a West Loop bed-and-breakfast that opened in 2017. “There aren’t really any small spots like this in the city,” says the co-owner of Esmé, a fine-dining restaurant in Lincoln Park. Housed in a historic, early-19th-century building, the 11-room Publishing House is run by husband-and-wife innkeepers Shawn Uldridge and Kimberly Lowery (and populated by two house pugs, Angus and Louie). “It’s super-intimate and can even be rented out for an entire party, which I find to be beyond unique,” says Bravo, who first stayed at the Publishing House for a friend’s wedding. “My good friend always stays there when she’s in town, and I visit her while she’s there.” The rooms are each inspired by an author who wrote a book based in Chicago, and come with claw-foot tubs, vintage kilim rugs, and amenities like plush bathrobes and Malin + Goetz toiletries. Common spaces include a third-floor room with a grand piano and sofas near the fireplace, plus the Press Room wine bar and regular dinner events with noteworthy chefs, such as Sarah Grueneberg of Monteverde.
When assignments take Los Angeles photographer Laure Joliet to Chicago, she prefers the Gray for its historic appeal. Originally built in 1894, the former New York Life Insurance Building was redesigned in 2016 and is now a Kimpton property. “The entrance and lobby have an impressive and imposing marble staircase that is of a scale and grandeur that you don’t normally experience,” says Joliet, who “loves the play between the history present in the architecture and the beautifully modern and updated rooms.” Don’t be misled by the buttoned-up interiors: Top-floor restaurant Boleo features a Peruvian and Argentinian street-style menu, and resident DJs turn the space into a nightclub — although Joliet’s favorite spot is the “fantastically cozy, library-style bar, Vol. 39.” The hotel also offers a menu of recreational equipment: Yoga mats can be found in each room (custom classes are available to book), bikes are available upon request, and fleece-topped dog beds and Micro Kickboard scooters are available for any dogs or kids in tow.
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