Something is in the air in the Windy City. It’s a city of contradictions; a bustling metropolis that hasn’t forgotten its Mid-Western charm; a city in a garden (a phrase that would become Chicago’s motto) where some of the world’s first skyscrapers are framed by the 26 or so miles of beaches along Lake Michigan. It shouldn’t work, and yet it does. Perhaps that’s why James Bryce described the city as “the most typically American place in America”.
The second most visited city in the US has seen a form of renaissance in recent years, becoming a focal point in leisure and culture. Fans of the TV show The Bear will instantly recognize its culinary spirit. Whether that’s the array of deep dish pizzas and hot dogs that instantly come to mind, or one of the 21 Michelin-starred restaurants that the city boasts.
Those looking for an equally luxurious place to lay their heads will be similarly spoilt for choice – that’s why we’ve narrowed down our selection of the very best hotels Chicago has to offer.
[See also: The 12 Best Restaurants in Chicago]
The St. Regis Chicago
Even if you have never heard of the brand’s luxurious global reputation, it’s hard to ignore the St Regis Chicago. Despite only opening its doors in 2023, the hotel quickly became a landmark only in Chicago’s hospitality scene, but the 101-story tower that it calls home was instantly a staple in the city’s distinctive skyline. The hotel occupies 11 stories of this undulating tower designed by Jeanne Gang – the tallest in the world designed by a female architect – and it truly raises the bar on what a boutique luxury hotel can be.
Despite the impressive views from the floor-to-ceiling windows and the inherent lux design – including a butler for every room – the atmosphere remains cool and casual, with pet-friendly rooms on offer and staff on hand to provide the perfect recommendations for a night in the Windy City.
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Top suite: Two-bedroom Presidential Suite
Set 1,198 ft above the ground, the Two-bedroom Presidential Suite offers true luxe amongst the clouds. KTGY Simeone Deary Design Group, the design team that worked on the suite, was largely inspired by the city’s rich architectural history as well as its myriad of carefully planned green spaces and twisting shorelines. The minimalist decor and use of earthy hues, combined with the free-floating, four-poster bed, a generous walk-in closet, private fitness room, butler’s pantry and an impressive primary bath – featuring an oversized soaking tub and steam shower – provide visitors with the ultimate in contemporary luxury.
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Chicago Athletic Association Hotel
A historic downtown hotel found on the doorstep of Millennium Park, the Chicago Athletic Association Hotel is a tribute to the city’s rich cultural history. The walls of this restored 1893 Venetian Gothic Tower must tell the city’s most infamous stories, as many a celebrity – notorious or otherwise – have been spotted here at some point or another. Formerly a private gentleman’s club for over a century, when it reopened its doors as a hotel in 2015, the interiors retain the same character of that bygone era. Think dark woodwork, vintage leather furniture, stained-glass windows and oversized stone fireplaces.
Many a handshake deal has been made here – and subsequent celebrations hosted afterward. There are seven food and drink establishments on the site, including the trendy hangout Cindy’s, situated within a vaulted steel rooftop atrium, which serves refined American fare.
Top suite: Founders Suite
The expansive 867-sq-ft Founders Suite is the true showcase of the Chicago Athletic Association’s rich history. Steeped in original character, from the working fireplace in the sitting room to the freestanding wrought-iron bathtub overlooking Michigan Avenue, this suite will keep you cozy and entertained throughout your stay.
The intricate woodwork and original stained-glass windows give the suite the feel of true craftsmanship and its French doors unveil stunning downtown Chicago views across Michigan Avenue to Millennium Park, The Bean and Lake Michigan beyond.
Park Hyatt Chicago
Found just mere steps away from the historic Water Tower Park and Michigan Avenue, the Park Hyatt Chicago offers a quintessential stay at one of the city’s landmark addresses. Reimagined and updated in 2022, the five-star residence embraces elements of its surrounding city with a distinctive calming design, offering a truly urban oasis amid downtown Chicago. Featuring museum-quality works of art, award-winning dining at restaurant NoMI and a dedicated personal service team, the Park Hyatt Chicago is an ideal choice for the discerning Elite Traveler.
Top suite: Presidential Suite
The Presidential Suite offers guests the ambiance of a well-appointed residence with all the amenities of a world-class hotel; including butler service, 24-hour concierge, and clothes pressing and shoe shining service. The magnificent views of Lake Michigan, the suite’s marble foyer, expansive living space, and separate office and kitchen areas provide the elite traveler with the ultimate lavish surroundings to make the most of their stay in the Windy City.
Four Seasons Chicago
The Four Seasons Hotel Chicago, an icon on the Magnificent Mile and a staple in the city’s luxury hospitality scene for more than 35 years, has undergone a series of facelifts over recent years. Since 2021, the hotel has worked on several extensive renovations, fully transforming from its suites to spa to its 23,00 square feet of social spaces. The transformation hasn’t gone unnoticed, in fact, Four Seasons Hotel Chicago snagged Interior Design Magazine’s award for best redesign just last year.
Food options are equally esteemed: frequently named a top dining destination in the Gold Coast, Adorn Restaurant showcases contemporary American cuisine created by TV chef Richie Farina and team. Meanwhile, the Adorn Bar, known as a place to be seen in downtown Chicago, is an intimate lounge with hand-crafted cocktails and premium spirits.
Top suite: Presidential Suite
Perched on the 46th floor with the tallest hotel views in the city, the Four Seasons Presidential Suite matches the breathtaking views of its exterior with the grandeur of its interior. Silk wall coverings, custom-designed carpeting and modern art provide the perfect blend of classic and contemporary, while amenities like the personally stocked wet bar and daily laundry service ensure the room’s luxury is extended to every part of your stay.
Designed by Rottet Studio, the sprawling suite includes three bedrooms and three bathrooms and can be configured to adapt to suit the needs of any guest. A private fitness room features a treadmill, elliptical trainer, weight bench, free weights and Pilates mats, as well as a state-of-the-art television, while the dining room and social areas offer seating for up to eight. To top it off, a personal concierge is on hand to cater for all your technological needs upon your arrival.
Waldorf Astoria, Chicago
Staying true to the brand’s global reputation, the Waldorf Astoria is bursting with quintessential luxury. Stepping from the cobblestone courtyard into the bright, double-height lobby feels akin to entering a modern art museum, where the shimmering chandelier, modern artwork and wall-to-floor marble elude opulence.
The onsite amenities are equally glamorous. The Waldorf Astoria Spa remains renowned for its superior treatments and comprehensive packages, as well as a pool and generous health club, meanwhile, the Mercedes-Benz house car is on hand to tour guests around the city. Onsite restaurant the Brass Tack serves classic American cuisine while renowned cocktail bar Bernard’s remains the perfect exclusive evening lounge to unwind at your discretion.
Top suite: Presidential Suite
Located on the 26th floor, the 3,600 sq ft Presidential Suite provides luxurious quarters to take in the panoramic views of the Chicago cityscape and beyond. The lofty location and floor-to-ceiling windows allow for torrents of natural light to flood in throughout the day while Juliette terraces act as a perfect place to gaze at the twinkling city after sunset.
Each of the two king bedrooms has its own private terrace and is lavishly appointed. There is also a fully-equipped kitchen and dining facilities for up to six guests. There is a well-equipped fitness room, providing the perfect opportunity to burn off any late-night treats that may have been indulged from the hotel’s 24-hour room service. The suite also has three private entrances, offering the utmost discretion for guests needing higher levels of privacy.
waldorfastoriachicagohotel.com
The Drake
Celebrating more than 100 years of history and glamour on Chicago’s Gold Coast, no other Chicago hotel has inspired more legendary acclaim than The Drake. None of its original 1920s opulence has been lost over the years, instead, The Drake time-wraps back to a truly gilded age. With its sweeping staircase, harpist plucking in the lobby and afternoon tea served daily in the Palm Court, it’s easy to understand why the guestbook boasts entries from the likes of Queen Elizabeth II, Princess Diana, Walt Disney and Charles Lindbergh.
Refusing to compromise on its high standards, The Drake preserves its relentless dedication to maintaining luxury at any cost, providing guests with a level of prestige and refinement that is often hard to find.
Top suite: Princess Diana Suite
If its nickname wasn’t a giveaway, perhaps the framed photos that hang throughout the Presidential Suite will clue you on this suite’s previous occupier. And it’s not just the People’s Princess who has graced this suite either, but the suite can name the former Prime Minister of Australia, the Queen of Thailand and former First Lady Nancy Reagan in its guest book – meaning a stay here almost certainly cements your place among the elite. With velvet upholstery and rich drapery throughout, it offers a truly decadent stay.
Viceroy Chicago
Located on Chicago’s Gold Coast within a 120-year-old building, Viceroy Chicago seamlessly blends old-world charm and contemporary allure. The preserved brick and terracotta façade pays homage to Chicago’s architectural history, while the interior, adorned with striking gold and black accents, complements the vibrant cityscape visible through floor-to-ceiling windows.
Eating at Lee Wolen’s – a Michelin-starred chef – Somerset is a must for anyone staying at the hotel. The restaurant has been designed to look like a glamorous yacht club with gilded mirrors and plentiful art deco lighting. His seasonal American menu changes regularly, but signature dishes include the smoked beet tartare and squid ink chitarra. Head to the 18th floor to experience Devereaux, a rooftop lounge that offers delectable cocktails in front of stunning skyline views across Chicago. A seasonal pool also makes this a popular daytime hangout in the summer.
Top suite: Penthouse Suite
Perched on the 16th floor, the Penthouse Suite offers panoramic vistas of the Gold Coast and Lake Michigan through expansive floor-to-ceiling windows. Spanning 1,675 sq-ft, this luxurious suite comprises two bedrooms, a spacious six-person dining area, a dedicated butler space for seamless service, and a state-of-the-art 75-inch Samsung Smart TV. Additionally, the suite boasts its own private media room.
Step outside onto the outdoor terrace to savor the breathtaking views and enjoy the refreshing Lake Michigan breeze. This terrace doubles as an ideal setting for evening entertainment, providing guests with a perfect retreat to unwind and take in the beauty of the surroundings.
viceroyhotelsandresorts.com/chicago
The Langham, Chicago
Housed with a skyscraper designed by renowned architect Mies van der Rohe, The Langham has put tremendous emphasis on doing the great man justice. The interior boasts an extensive collection of fine art while the public spaces have been designed to complement the steel-and-glass building.
The Langham’s renowned executive chef Damion Henry produces stylish dishes to match at the destination restaurant Travelle. While the menu is dominated by seasonal American classics, Henry prides himself on unique techniques and culinary presentations inspired by his Jamaican heritage. He utilizes his close connection with some of the finest farms, ranches and orchards in the US to source only the freshest of ingredients. True to its British roots, The Langham also serves a delectable afternoon tea in the Pavilion.
Club-level guests benefit from a team of butlers who will do everything from press clothing to drawing a bath. The award-winning Chuan Spa and the 67-foot tranquil swimming pool offer guests the chance to relax.
Top suite: Infinity Suite
Described as an opulent retreat in the heart of Chicago, the Infinity Suite is designed to offer a tranquil place to relax following a long day. The suite boasts two well-appointed bedrooms with ensuite bathrooms and floor-to-ceiling windows with spectacular views. The dining facilities allow for up to ten guests while a fireplace and a custom-painted grand piano make for an elegant evening of entertainment.
The Peninsula Chicago
A distinguished member of the Hong Kong and Shanghai Hotels group, The Peninsula Chicago boasts a rich heritage, blending Far East graciousness with warm Midwestern hospitality.
Nestled in the heart of Chicago’s Magnificent Mile, the hotel offers 339 spacious guestrooms and suites adorned in a splendid classical style, seamlessly paired with cutting-edge technology. Each accommodation features a king-sized bed, expansive televisions, and window-side dining tables. Renowned for its opulent comfort and flawless service, The Peninsula stands as the preferred choice for Hollywood A-listers and VIPs.
Indulge in relaxation at The Peninsula Spa before savoring European favorites in a modern setting at Pierrot Gourmet. Conclude your evening at the chic Z Bar, one of the city’s premier rooftop lounges, boasting iconic views and expertly crafted cocktails.
Top suite: The Peninsula Suite
Overlooking Michigan and Chicago Avenues on the hotel’s 18th floor, the Peninsula Suite exudes a truly timeless elegance. From the baby grand piano to a wraparound terrace with its own Jacuzzi, every amenity is at your disposal. With the capacity to be seamlessly converted into a one-to-three-bedroom suite, or with an entire wing easily blocked off for guests requiring extra privacy, The Peninsula can cater for every need.
The Ritz-Carlton, Chicago
Set atop Water Tower Place, high above prestigious North Michigan Avenue, The Ritz-Carlton Chicago offers a setting of unmistakable grandeur.
Featuring beautifully style guestrooms with exquisite décor and breathtaking views, as well as a newly renovated grand lobby complete with a truly iconic fountain; The Ritz-Carlton Chicago is unmistakably a world-class hotel. The hotel’s in-house Torali restaurant offers contemporary brasserie-style cuisine such as fresh pasta and dry-aged steaks in a modern and refined space.
You can also head to the rooftop bar to bask in the sunshine while sipping on sundowners and snacking on Italian-inspired bites. The hotel’s exclusive added extras include a full-service spa and fitness club as well as complimentary access to the hotel’s exclusive Club Lounge.
Top suite: Presidential Suite
The two-story Presidential Suite boasts a spiral staircase, beautiful modern interiors, and floor-to-ceiling window views of Lake Michigan, from the corner of the 25th and 26th floors. The spacious two-bedroom suite also includes a kitchen; living, dining and study rooms; and three full marble bathrooms, plus two guest powder rooms. The extravagant media room houses a baby grand piano and a state-of-the-art surround-sound stereo system. Guests of this illustrious suite can enjoy amenities as impressive as their accommodation: a 24-hour personal assistant and transportation to and from the local airport.
[See also: The 5 Best Spas in Chicago]
