"Chicago Athletic Association Hotel Hyatt heir John Pritzker spared no expense repurposing the 1893 home of the Chicago Athletic Association into one of the city’s most original, not to mention best located, boutique hotels. Local architects Hartshorne Plunkard retained the Venetian Gothic exterior, ornate millwork, stained glass, tiles, and cast-iron reliefs and added Cindy’s, avaulted rooftop atrium restaurant space styled after a modern Lake Michigan beach house offering stupendous views of both the lake and Millennium Park from its alfresco terrace. Cooper Hewitt award–winning design team Roman and Williams preservedthe massive19th-century working fireplaces and elaborate sports-themed woodwork in the original members’ Drawing Room, filled with vintage chairs, modern sculptures made out of antique sporting trophies, and various books about Chicago sports heroes, politicians, and mobsters. Guest rooms feature stylish riffs on athletic-club culture including leather settees that resemble pommel horses; leather club chairs and sofas, updated versions of brass beds, and national park blankets add to the retro vibe. The famous pool where Johnny Weissmuller swam laps with club members did not survive the transformation (it's now an event space), but kids of all ages love the huge, dark-wood retro Game Room with bocce balls, billiard tables, andchess."

"Walk into the Freehand, a remodeled 1920s dive, and you’ll think it’s a millennial fantasy boutique hotel with its artisanal cocktail and coffee bars, and intensely curated wood-paneled clubhouse lounge filled with leather chairs, blue settees, and a Wurlitzer electric keyboard for guests to play. You can book a conventional private hotel room here, but it’s the 80 shared quad bedrooms that are the draw—and the city’s best bargain—at this reinvented, upscale “youth” hostel footsteps from Michigan Avenue’s Magnificent Mile. Designed by Cooper Hewitt award-winning firm Roman and Williams, the rooms include deep-blue bath tiles and mahogany wood beds that were inspired by Lake Michigan but recall vintage ocean liner cabins (in size as well as color scheme). Communal rooms, co-ed or female only, have a bathroom, gym-style locker bank and four bunk beds each with a private lamp, reading shelf, and charging station. The clientele includes families with kids and budget-minded elders as well as youthful nomads, all of whom appreciate the guest kitchen and laundry rooms, and, especially, the staff’s friendliness. There is a cafe and a cocktail bar, and daily blackboard posts listing concerts, poetry readings, festivals, and other events and eateries outside the Michigan Avenue tourist orbit."

"Thispurpose-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 inivoryand gray tones. Higher floors offer spectacular views of Lake Michigan and Navy Pier.Service here gets high marksfor 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."

"In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is different, but all are stylishly simple and feature details such as wood floors, exposed brick, original art work and site-specific installations by local artists, cassette players with mix tapes, well-curated minibars, and Aesop toiletries. For the noise averse, the hotelreminds potential guests that the rooms are located above "an occasionally raucous, whisky-fueled tavern."

"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 thegeodes, 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."

"Soho House Chicago The skeleton of the new Chicago Soho House once belonged to a belt factory—and though the space has been luxuriously renovated and fit with plush leather chairs, over 250 pieces of art, chandeliers, and beds with Egyptian cotton sheets, the hotel still nods to the West Loop neighborhood’s industrial history. Unlike other locations of this hip members-only club, Chicago’s Soho house offers some access to the public, winning over both guests and locals with its comfortable first floor and mezzanine areas, Cowshed spa, and eateries like Chicken Shop, which specializes in free-range rotisserie chicken. Soho House’s members are generally creative, open-minded types who prefer comfort over formality. Anyone, however, can book a hotel room—and with a room key comes all the perks afforded to members, like access to all restaurants, the gym (which features a professional boxing ring), a movie screening theater, and the swanky rooftop pool and bar. Rooms come in sizes tiny, small, medium, medium plus, and big, and are peppered with delights like china tea sets and crystal decanters."

"Why we love it: A boutique stay that immerses guests in the pleasures of Hyde Park The Highlights: - A unique location away from the Mag Mile strip - Thoughtful decor that pays homage to Hyde Park’s storied past - Record players and books by local authors in each room The Review: Those seeking a Chicago stay far from the busy Magnificent Mile will find serenity at SOPHY, a boutique hotel on Chicago’s South Side. Situated in the historic neighborhood of Hyde Park (home to the 1893 World’s Columbia Exposition), the property is near some of Chicago’s greatest sites, including the University of Chicago, the Museum of Science and Industry, and the future Barack Obama Library. Inspired by the art, music, and literature of Hyde Park, interiors—designed by Stonehill Taylor—include wallpaper featuring a Nobel scientist’s blueprints, lobby lamps made from brass trumpets, and books by local authors in each room. A few more novels line the shelves at on-site restaurant MESLER, which serves a menu of comfort fare (think chicken and waffles, house-made pasta, and a signature burger). Post-dinner, retreat to your room and unwind with plush bathrobes, slippers, and some tunes—a record player and selection of Chicago blues vinyl are at the ready."

"Why we love it: A hip hotel where London style meets Midwestern hospitality The Highlights: - A prime location in one of Chicago’s most of-the-moment neighborhoods - Three vibrant dining outlets from acclaimed local chefs - A rooftop pool with epic skyline views The Review: Opened in April 2019 as The Hoxton’s third stateside property, this Chicago hotel sits on the site of a former meatpacker in the Fulton Market District, just steps away from some of the area’s best (and newest) restaurants, bars, and shops. Three categories—Snug, Roomy, and Cosy—categorize the 182 rooms, which were designed by Ennismore Design Studio to exude vintage flair while reflecting the neighborhood’s industrial past. The aesthetic is evident in unfinished concrete ceilings and warehouse-style windows, along with mid-century furniture, brass bed lamps, and Marshall radios. Comfortable as they are, rooms here will likely serve as late-night sanctuaries only, as guests will be spending most of their time at the many buzz-worthy dining outlets on site. Cabra is the latest from Top Chef winner Stephanie Izard, who pays homage to her recent South American travels through an array of seasonal ceviches and tiraditos. Try Cira for chef Chris Pandel’s take on all-day Mediterranean fare, and Lazy Bird for live music and a menu of 50 classic cocktails from beverage director Lee Zaremba. When you just want to hang, grab a seat on a comfy sofa in the lobby lounge, or head up to the roof, where the pool offers sweeping views of the city."

"The Langham, Chicago Opened in 2013 as the Hong Kong –based brand’s U.S. flagship property, the Langham, Chicago elegantly occupies the first 13 floors of the former IBM Building, a modern American landmark designed by Ludwig Mies van der Rohe, whose views of the city’s skyline nearly rival those along the famous architecture boat tour on the Chicago River. The iconic 52-story blacktowerhas light-filled rooms, efficient staff, a contemporary Seasonal Americanrestaurant and afternoon tea, a Chuan spa, and location within walking distance of both the Loop and major sites suit both the business and leisure traveler. Many rooms have striking views of the river out the floor-to-ceiling windows; suites have reproductions of van der Rohe’s iconic Barcelona chairs and daybeds."

"The 20-story Peninsula Chicago sits just off—yet feels distant from—the shop and tourist–congested Michigan Avenue. An elevator ride up to the fifth floor leads guests to one of Chicago ’s grandest hotel lobbies. Marble floors and gilded 20-foot ceilings evoke colonial Shanghai , a live string quartet performs out of sight, and an army of efficient concierges stands ready to answer any whim. Care to find Lake Michigan’s best smoked whitefish? Meet a craft brewer of truffle-infused beer, or take a helicopter ride over the city? The service-obsessed hotel management encourages guests to look beyond the tourist zone by arranging private tours of offbeat museums and neighborhoods. Large, light-filled rooms with French doors separating lounge and sleeping areas especially suit families with kids, as does the large indoor pool and hotel activities such Cantonese dim sum cooking lessons and weekend chocolate buffets."

"Thompson Chicago , housed in a contemporary high-rise in the heart of the Gold Coast luxury dining and shopping scene, was overhauled in 2013 by British designer Tara Bernerd. It offers a winning combination of modern-retro style, a home-away-from-home ambience, attentive service, and value for money. (The building previously was home to the Sutton Place Hotel.) With Thompson Hotels’ arrival, the lobby, dominated by a huge shelved library cube filled with books, curios, and retro bull's-eye mirrors, now strikingly harmonizes industrial exposed brick and dark-wood beams with elements paying homage to Chicago architect Frank Lloyd Wright (think geometric tiles and a cantilevered staircase).Most guestrooms have astounding city and Lake Michigan views, and all are snazzily furnished with asymmetrical velvet sofas, enormous showers, and framed contemporary art by the likes of Wes Lang. It's a style that impresses without being intimidating."

"Virgin opened its first U.S. hotel in a 26-story, 1920s art deco tower. Originally a Chicago bank, the building’s high-ceilinged, second-floor hall has been transformed into the Commons Club, a socializing spot divided into a lounge, dining room, and oval-shaped zinc bar with red leather seating and power outlets for tech-addicted travelers. Apartment-like rooms are smartly divided by sliding doors into two sections: a sleeping lounge, and a large dressing and bath area. The Virgin brand’s red-and-white logo is referenced in retro-looking red Smeg mini-fridges stocked with treats at street prices and eye-catching seats made from repurposed red Vespas. With in-house concerts, live DJs, and other performances at the rooftop Cerise lounge, the hotel entrance is sometimes clogged with clublike lines of locals, with security checks that delay guests trying to return to their digs. The live-like-a-local esprit extends to machines for brewing artisanal Chicago Bow Truss brand coffee in your room and, especially, to the hotel’s online itineraries curated by local artists, food and fashion bloggers, and digital entrepreneurs whose tips transport visitors outside the usual tourist bubble. Lifestyle amenities also include yoga mats in the rooms and a free app for using your smartphone to control lights and communicate with the courteous, helpful staff."

"When the Waldorf Astoria took over the swank Elysian Hotel in 2012, it preserved the sumptuous room decor, the 14,000-square-foot spa, and the Greek Classicism–meets–French 1920s aesthetic. Located on the first 27 floors of a 60-story luxury condominium high-rise amid Chicago ’s toniest shopping district, the Waldorf Astoria Chicago feels surprisingly calm and intimate thanks to French-born architect Lucien Lagrange’s creation of a motor court entryway and a lobby reminiscent of an 18th-century Paris mansion (although the heatedcobblestone porte-cochere means winter guests never step out of their Bentleys or taxis into snow). Guestrooms are some of the largest in Chicago, with amenities like TV screens embedded in mirrors that face deep soaking tubs, andgas fireplaces. Apart from street noise filtering up to rooms on the lower floors, the atmosphere is serene, and the service courteous and ultra-efficient even with a no-tipping policy. In 2017, acclaimed chef Michael Mina made his Chicago debut at the Waldorf, opening not one, but two, restaurants.Margaux Brasserie offers elevated French cuisinecombined with locally sourced ingredientsand Petit Margaux is a French patisserie on the lobby level."

"On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago , attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods. Rooms occupy one of the city’s rare surviving 1890s row houses, while apartments with fully equipped kitchens and hardwood floors occupy the first floor and the garden-facing basement of the owner’s residence (a three-story late 19th-century walk-up, just across the street). Individually decorated, rooms and apartments share an elegant, homey look. Four on-duty innkeepers provide personalized service and expert recommendations on the local scene."