‘Windy City’ Chicago is all about the upscale Magnificent Mile, the wonderful art installations at Millenium Park, and the lakefront beaches. The city is the perfect blend of burgeoning creative neighborhoods such as West Loop and glitzier ones such as the Gold Coast. What’s more, Chicago is no stranger to opulence either, whether it’s fine dining at Aliena, Everest, or Oriole or the glittering and high-end boutiques at the Magnificent Mile. And all this is without even mentioning its gloriously expensive and luxurious hotels. Chicago most expensive hotel options range from a Trump Tower outpost to a Four Seasons one. Moreover, they feature everything from decadent dining and drool-worthy art collections to spas that feel like hedonistic unwinding spaces. Clearly, the most expensive hotels in Chicago are about more than just expensive rooms.
What also helps along Chicago’s larger-than-life repute is its larger-than-life attractions and sights. For instance, Navy Pier and Millenium Park are two of the top tourist attractions in the USA! What’s more, Brookfield Zoo, a.ka. Chicago Zoo is one of the world’s largest zoos. And if that wasn’t enough, Chicago is one of the country’s top cities with most skyscrapers, with the Sky Deck at Willis Tower even featuring amongst the world’s best viewing platforms & skywalks! So, here’s to a wonderfully lavish and luxurious vacation at one of the most expensive hotels in Chicago; read on!
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The Downtown-located Langham is one of the most expensive hotels in Chicago. Miles van der Rohe’s last skyscraper is the pinnacle of Chicago’s riverboat architecture and paragon of the late International Style. The hotel occupies the first 13 floors of the skyscraper and makes you feel like a spy thriller character as you step into the mid-century lobby. Clearly, this is Chicago’s finest address. Attention to detail is paramount here, whether it’s the Chuan Spa bathroom products or the bathroom glass becoming opaque in a click. The service is matchless, with the staff going the extra mile to make you feel like a VIP. Don’t miss a visit to the Chuan Spa, making Langham one of Chicago’s best spa hotels. What’s more, staying in club-level rooms even gets you your own personal butler.
But, the most expensive rooms of them all are the two presidential suites, both of which cost a cool 8,000 USD per night. Each of them has two bedrooms with ensuite bathrooms, a private butler pantry, a formal 10-seater dining table, and oversized living rooms with fireplaces and spectacular views of the city.
Four Seasons Hotel
At the Four Seasons in Chicago, you feel like you’re on Cloud 9 – or rather Cloud 30th, because that’s where the rooms begin! The pampering begins in the art-filled lobby and doesn’t stop even after you’ve checked into the rooms, which offer jaw-dropping views of the lake or the city. So, there’s a distinct feeling of seclusion and serenity, with great views to boot. You’ll love the 1940s French decor-inspired rooms with spa-like bathrooms filled with Chinese marble. The lone restaurant Allium serves some of the city’s most delicious meals, but it’s the wellness facilities that you’ll love. For instance, the 50-feet-long indoor pool with Roman columns is a real treat, thanks to the whirlpool, lounge chairs, and skylight. Oh, and there’s a lovely spa as well.
The most expensive digs at this Four Seasons Hotel is the presidential suite, which pays 9,000 USD per night. The 2,000 square feet-huge room of luxury sits on the 46th floor and overlooks Lake Michigan. Expect a massive living room, a private bar, a private fitness room, and three marble bathrooms – oof.
Waldorf Astoria Chicago
The Waldorf Astoria is one of the most expensive hotels in Chicago, and it shows. Opulence isn’t simply a design feature at this Windy City Waldorf outpost; it’s an ethos. Your first glimpse is a massive, shimmering chandelier at the end of the brick-paved drive that leads to the hotel. What’s more, the entire hotel is full of glossy black doors, plush velvet couches, and crystal baubles. There’s even a constantly updated roster of the best and most happening goings-on about town, from Craft Beer Week to Cubs games. The fabulous bar and restaurant aside, the hotel also boasts a dreamy spa with an indoor pool, the perfect place for unwinding.
Even entry-level rooms are so chic that you’ll keep Instagramming the heck out of them. The suites are even more decadent, especially the Waldorf Suite, a super-deep marble soaking tub. But, the most indulgent of them all is the Presidential Suite, which costs at least 5,000 USD per night.
The Ritz-Carlton Chicago
The Ritz-Carlton puts on the ritz – and how. This Gold Coast hotel is one of the swankiest in the Windy City and specializes in showering guests with attention. The eye-popping design begins right from the 12th-floor lobby, decked out in glamorous 1920s decor. Think a Czech glass art ceiling installation and museum-quality artwork. The Olympic-sized pool with lap lanes, the 11th-floor spa, and the 24/7 fitness center with Navy Pier views are cherries on top of a very large and rather indulgent cake. Even dining is an experience, right from the classy marble-and-copper lobby bar to the super-casual Torali Bar that serves delectable Italian cuisine.
The rooms and suites are something else and mimick old Hollywood grandeur with black, platinum, and cream hues. Moreover, huge picture windows beautifully frame views of the city’s skyline or Lake Michigan as you enjoy your favorite movie on Netflix. Plus, the marble bathrooms with slippers, robes, designer toiletries, and lighted make-up mirrors keep everything, and you, looking good. It’s no wonder that peeps who come to Chicago love staying here, as it’s one of Chicago’s best business hotels. And what also helps is that the most expensive room in the house, the Presidential Suite, costs 1,400 USD per night to rent.
The 96-year-old Drake is one of the most expensive hotels in Chicago. Chicago might have its share of historic hotels, but this national landmark of a hotel has a venerable status and is akin to a well-preserved museum. Curated tours are a specialty at this hotel, such as the historic tea service tour, a self-guided tour-and-pour at the iconic bars, or even the ‘American Girl’ tour for kids. Are you here for Halloween? Don’t miss the coveted haunted theme tour, which is almost always booked. Ascend the formal royal blue staircase to the lobby, complete with elaborate fresh flower arrangements and a towering crystal chandelier. The dining establishments, the ornate fountain-bedecked Palm Court, and the Coq D’Or bar are the crowning jewel of amenities here. In fact, it was only the second bar that got a liquor license after Prohibition was repealed!
The rooms are old-world, but with distinct modern touches such as flatscreen TVs, lakeside views, and all-marble bathrooms with Peter Thomas Roth bath products and bathtubs. And if you stay in the best room, i.e., the Princess Diana Suite, then it’ll cost you as much as 2,000 USD.
The Thompson Chicago is a luxury hotel with a bite. Foodies and fashionistas abound at this slick hotel, which has elements of Prairie School architecture with organic accents. You don’t even have to leave the hotel to dine at one of Chicago’s best restaurants, the lobby-level Nico Osteria, that serves seasonal farm-to-table Italian fare. It’s also famously known for its European breakfast, which has been called “divine.” And if you find the secret stairwell between the 2nd and 4th floors, it leads to a room with murals made by local artists.
Even the least expensive rooms have great views of the skyline, but for a wee upgrade, you are awarded sublime views of Lake Michigan. The masculine color scheme of neutrals with rich browns and the abundance of pillows make for a very cozy and homey nest. The Penthouse, the most expensive room, will set you back by a cool 2,500 USD per night, but it sure is worth it.
Trump International Hotel & Tower
The Trump International Hotel & Tower is easily one of the most expensive hotels in Chicago. The name “Trump” might be polarizing on Chicago’s streets, but it’s all business inside the arresting 92-floor structure. It’s also Chicago’s tallest hotel and offers unparalleled views of the Chicago skyline and the river. Two Michelin-starred restaurants aside, guests make a beeline for the 14ht-floor wellness trifecta. This includes a fitness center with wraparound windows, an indulgent spa, and a jaw-dropping 75-foot swimming pool. But, don’t miss heading to the 16th-floor rooftop with a terrace, where you can drink cocktails to unparalleled views.
Even the smallest rooms here are larger than some Chicago apartments! Imagine separate seating areas, huge plush beds, kitchens with Nespresso machines, and huge floor-to-ceiling windows. Plus, they don’t have minibars – they call them “water libraries,” which are studded with Swarovski crystals – as OTT as it gets. The Grand Deluxe Two-Bedroom Suite is the most expensive, with rates at 1,300 USD a night.
Sofitel Chicago Magnificent Mile
The Sofitel Chicago Magnificent Mile might be the crowning glory of the upscale and expensive shopping district. This French import of a hotel serves up European hospitality with an edge of ‘haute couture.’ The hotel makes an impression right off the bat with the natural light-filled two-story atrium. Plush couches and lounging nooks aside, you’ll also find infused water and fresh flower arrangements. Instagrammers go click-click at night when the French opera house-inspired grand staircase lights up with 5,000 twinkling lights. A bar and a restaurant, and a 24-hour SoFit Gym ensure that you’re never running short of things to do and explore here. Does something smell good everywhere you go? The hotel has a custom perfume scent, Essence de Sofitel, by French perfumer Lucien Ferrero.
When it comes to the rooms, they’re simple yet elegant with cityscape backdrops via floor-to-ceiling windows. The signature SoBed beddings ensure a good night’s sleep, while the marble bathrooms feature Lanvin designer products and luxury bathtubs. The Presidential Suite, the most expensive room, costs as much as 2,000 USD to rent for staying a night.
Nobu Hotel is one of the most expensive hotels in Chicago. The hotel nurtures life in balance – its tranquility in the rooms and party on the rooftop! Nobu is a serene refuge behind the tinted-glass facade, right from the oshibori hand towel and welcome drink-handing ritual to the indoor tranquility pool. There are multiple foodie hideaways to enjoy chef Nobu Matsuhisa’s signature fare, including the mezzanine sushi bar, the grand ground-floor restaurant, and the 11th-floor rooftop. Your breakfast is brought to your room and includes the chef’s creative geniuses, such as salmon egg donburi. Work up an appetite with a swim in the 40-foot indoor tranquility pool, nothing less than an urban onsen.
At its best, the rooms are Japanese minimalism; think yoga mats, recessed lighting, blond wood, and crisp platform beds. Natural light floods in through the floor-to-ceiling windows. The Yubune rooms/suites feature teak soaking tubs and custom Natura Bissé bath products if you want some indulgence. But, the zenith is the Nobu Villa, which costs upwards of 3,000 USD per night.
The Loews Hotel hits all the right notes, from amenities to services and even the digs. The lake and riverfront hotel is set in a serene neighborhood surrounded by highrises, which means million-dollar views. The lobby with ornamental metalwork, a fireplace, inviting armchairs, and soft leather couches are a social hub. Fitness freaks will love the massive fitness center, while those who’re loving their laidback holiday can hang out in and by the indoor lap pool. What’s more, there’s even an onsite spa for relaxing massages and treatments. When it comes to food, the hotel does fabulously. For one, there’s an Argentine steakhouse serving delicious meals and a lobby lounge that serves a decadent breakfast. Thanks to Starbucks, you can have coffee any time and come happy hour; Streeterville Social is where you should be.
The casual-contemporary rooms and suites are spacious, with the dove grey-and-white palette and floor-to-ceiling windows lending a sense of calm. Thanks to the blackout blinds, you can sleep for as long as and any time you want to. The largest and most lavish suite, the Presidential Suite, costs at least 2,000-2,500 USD, which means it’s perfect for a splurge-worthy vacation.
The Peninsula is, without a doubt, one of the most expensive hotels in Chicago. Zip up five floors to the swanky lobby, which feels like a private Zen space with high ceilings and gold reliefs. Cocktails by the fire, afternoon tea – everything is served here. Did we tell you that the lobby is a Michelin star restaurant? Yes! Dining is another reason to stay here; for instance, the 1930s supper club-like Shanghai Terrace serves delicious Cantonese food. But, the rooms – whew! They’re elegant to the last thread, with floral wallpaper and sexy navy accents. However, it’s the bathrooms that’ll take your breath away. Imagine a deep-soaking bathtub with a TV in the front, L’Occitane toiletries, and slippers and bathrobes.
Og them all, it’s the Peninsula Suite that’s not just an expensive room, but one of the city’s most expensive rooms – it costs more than 10,000 USD per night! This opulent suite features a baby grand piano, a wraparound terrace with mesmerizing views, and three bedrooms. The hotel is also one of Chicago’s most pet-friendly hotels, with the pet fee being just 50 USD for the entire stay!