Chicago, a vibrant metropolis nestled against the shores of Lake Michigan, is renowned not just for its iconic skyline and rich cultural tapestry but also for its unparalleled luxury accommodations. This city, steeped in history and brimming with architectural marvels, offers an array of expensive hotels that promise an unforgettable stay. Each establishment is a testament to Chicago's commitment to excellence and luxury, catering to those who seek nothing but the finest during their travels.
In the heart of the Windy City, expensive hotels stand as beacons of opulence, offering unrivaled views, exquisite dining experiences, and impeccable service. These establishments are not merely places to stay; they are destinations in their own right. Whether it's the allure of staying in a historic building or the modern comforts and technologies of a contemporary hotel, Chicago's luxury accommodations leave no stone unturned in ensuring your experience is as majestic as the city itself.
For those ready to dive into the lap of luxury, Chicago's expensive hotels offer a gateway to exploring the city in style. From the Magnificent Mile, with its haute couture and landmarks, to the serene vistas of Lake Michigan, your stay will be accentuated with unparalleled comfort and elegance. Let this city, known for its dynamic vibe and breathtaking beauty, be your playground, with its most opulent hotels providing the perfect backdrop for an unforgettable journey.
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Our Top 10
(Sorted by rating & number of reviews)
1. Swissotel Chicago
2. The Palmer House Hilton
3. The Langham Chicago Hotel
4. W Chicago - Lakeshore
5. The Drake Hotel
6. The Peninsula Chicago Hotel
7. Four Seasons Chicago Hotel
8. Viceroy Chicago Hotel
9. The Ritz-Carlton, Chicago Hotel
10. Trump International Hotel & Tower Chicago
Historic Elegance: Timeless Expensive Hotels in Chicago
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Chicago
Dec 30, 2025 - Dec 31, 2025
Swissotel Chicago
8.4
Good
(902 Reviews)
+ 318 photos
Swissôtel Chicago's distinctive triangular structure offers a unique architectural landmark on the Chicago skyline, with a prime location that affords spectacular views of Lake Michigan and the Chicago River. The hotel's rooms and suites are designed with the guest's comfort in mind, featuring modern amenities and large windows that frame the stunning water views. Beyond the comfort of their accommodations, guests can enjoy innovative dining, a state-of-the-art fitness center, and a serene spa. Swissôtel Chicago merges Swiss hospitality with the heart of Chicago, providing a luxurious retreat for those looking to enjoy the city's vibrant culture alongside its natural beauty.
Address:323 East Wacker Drive
Rating:
Good
8.4
(902 Reviews)
Rooms:661
Price: From 215$
The Palmer House Hilton
7.5
Good
(925 Reviews)
+ 216 photos
Palmer House, A Hilton Hotel, is a jewel in the crown of Chicago's luxury accommodations. Stepping into its famously lavish lobby, guests are transported to an era of unmatched elegance and glamour. The hotel's luxurious rooms and suites, adorned with elegant furnishings and plush amenities, offer a perfect retreat in the very heart of the city. With its renowned Empire Room, historically a hotspot for entertainment and socialites, guests can experience a slice of Chicago's illustrious history. Palmer House also prides itself on modern luxuries, such as its full-service spa and health club, ensuring a stay that is both indulgent and rejuvenating. This hotel perfectly encapsulates the blend of historic charm and contemporary luxury that defines the most expensive hotels in Chicago.
Address:17 East Monroe Street
Rating:
Good
7.5
(925 Reviews)
Rooms:1641
Price: From 89$
The Langham Chicago Hotel
9.2
Good
(333 Reviews)
+ 157 photos
Already mentioned for its contemporary elegance, The Langham, Chicago also sets itself apart with its culinary offerings. The hotel's Travelle restaurant overlooks the Chicago River and showcases a seasonal American menu that draws inspiration from the Mediterranean. Under the guidance of a renowned chef, Travelle offers a dynamic, refined dining experience, complemented by a meticulously curated wine list and signature cocktails. The afternoon tea service at the Pavilion, inspired by The Langham's London heritage, offers a sumptuous selection of teas, sandwiches, and pastries, making it a sought-after experience in Chicago’s culinary landscape.
Address:330 North Wabash Avenue
Rating:
Good
9.2
(333 Reviews)
Rooms:316
Price: From 366$
Modern Marvels: Contemporary Expensive Hotels in Chicago
The Windy City is also home to some of the most stunningly modern and expensive hotels in Chicago, offering a different kind of luxury. These hotels stand out for their architectural brilliance, cutting-edge technology, and innovative designs that redefine the concept of luxury accommodations. They cater to the sophisticated traveler who appreciates the finer things in life, including state-of-the-art amenities, contemporary art installations, and forward-thinking environmental initiatives. The hotels in this section are selected for their commitment to providing a luxury experience that's not just opulent but also progressive and in tune with the needs of today's discerning globetrotters. Enjoy the blend of modern luxury and innovative services that these hotels bring to the table, setting the stage for a truly memorable stay in Chicago.
W Chicago - Lakeshore
7.9
Good
(1652 Reviews)
+ 70 photos
The W Chicago - Lakeshore directly faces the shimmering expanse of Lake Michigan, offering a waterfront escape right in the heart of the city. This hotel redefines luxury with its bold design, vibrant atmosphere, and exceptional service. Each room and suite provides a front-row seat to the lake’s tranquil beauty, complemented by contemporary, plush interiors. The hotel’s restaurants and bars capitalize on these views, creating an immersive experience. With its modern amenities, including a luxurious spa and state-of-the-art fitness center, the W Chicago - Lakeshore caters to those who demand the pinnacle of luxury with a side of stunning vistas.
Address:644 North Lake Shore Drive
Rating:
Good
7.9
(1652 Reviews)
Rooms:520
Price: From 169$
The Drake Hotel
7.9
Good
(574 Reviews)
+ 227 photos
A true icon of Chicago has been synonymous with luxury and elegance since its opening in 1920. Situated at the start of the Magnificent Mile, this historic hotel offers breathtaking views of Lake Michigan and the city's skyline. Guests can expect opulent rooms that blend historical charm with contemporary amenities, fine dining experiences that include the famous afternoon tea at Palm Court, and impeccable service that makes every stay memorable. The Drake is a testament to Chicago's rich history and tradition of hospitality, offering a stay that's as visually stunning as it is comfortable. It's not just a hotel but a piece of Chicago's cultural fabric, offering a luxurious gateway to the city's past and present.
Address:140 East Walton Place
Rating:
Good
7.9
(574 Reviews)
Rooms:535
Price: From 133$
The Peninsula Chicago Hotel
9.4
Good
(207 Reviews)
+ 269 photos
The Peninsula Chicago, known for its impeccable service and luxurious accommodations, also prides itself on its distinctive dining experiences. The Shanghai Terrace, a Michelin-starred restaurant, offers some of the city's best Chinese cuisine amidst the ambiance of 1930s Shanghai chic. Meanwhile, The Lobby restaurant serves contemporary American cuisine in a stunning setting, complete with soaring ceilings and floor-to-ceiling windows. The hotel’s commitment to culinary excellence is evident in every dish, making it a premier destination for epicureans visiting Chicago.
Address:108 East Superior Street
Rating:
Good
9.4
(207 Reviews)
Rooms:257
Price: From 400$
Lakeside Luxuries: Expensive Hotels in Chicago with Water Views
Chicago's magnificent lakeside location is a distinct aspect of its allure, with some of the city's most expensive hotels offering captivating views of Lake Michigan. These hotels not only provide luxurious accommodations but also feature breathtaking panoramas that connect guests with the natural beauty of the area. Ideal for those who seek a serene escape without leaving the city, these establishments offer a tranquil retreat. High-end amenities, gourmet dining, and impeccable service complement the stunning vistas to create an unparalleled lodging experience. In this section, we explore hotels that excel in blending luxury with mesmerizing water views, ensuring every stay is as visually splendid as it is comfortable.
Four Seasons Chicago Hotel
9.0
Good
(170 Reviews)
+ 225 photos
Perched near the edge of Lake Michigan, the Four Seasons Hotel Chicago offers an oasis of luxury high above the bustling streets of the city. Guests are treated to sweeping views of the lake and skyline from the elegantly furnished rooms and suites, which are designed to provide a peaceful and luxurious haven. The hotel's spa and indoor pool also offer a serene setting, further enhanced by the stunning backdrops. With its renowned service, exquisite dining options, and prime location near the Magnificent Mile, the Four Seasons Hotel Chicago is a beacon of luxury for those seeking a tranquil yet opulent stay in Chicago, making it a top choice among expensive hotels in the city.
Address:120 East Delaware Place
Rating:
Good
9.0
(170 Reviews)
Rooms:345
Price: From 403$
Viceroy Chicago Hotel
9.0
Good
(1590 Reviews)
+ 168 photos
Viceroy Chicago perfectly embodies the marriage of historical allure and modern luxury. Set in the exclusive Gold Coast neighborhood, the hotel greets its guests with a façade that harks back to the 1920s, while the interior showcases contemporary design at its finest. Rooms and suites boast floor-to-ceiling windows offering panoramic views of the city or lake, complemented by cutting-edge amenities and sleek furnishings. The rooftop pool and lounge offer an urban oasis, providing a perfect spot to unwind with spectacular views. Viceroy Chicago's commitment to luxury is evident in its attentive service and personalized guest experiences, making it a standout among the city's expensive hotels for those who cherish modern elegance.
Address:1118 North State Street
Rating:
Good
9.0
(1590 Reviews)
Rooms:180
Price: From 295$
The Ritz-Carlton, Chicago Hotel
8.7
Good
(77 Reviews)
+ 263 photos
Nestled in the prestigious Magnificent Mile, The Ritz-Carlton, Chicago stands as a beacon of luxury. This hotel elevates the standard of expensive accommodations in Chicago, combining exquisite design with unparalleled service. Each room and suite is meticulously appointed, featuring stunning views of the city or lake, marble bathrooms, and sumptuous bedding. Guests can indulge in the hotel's world-class spa, savor gourmet dining at its best, or simply bask in the elegance of its public spaces. The Ritz-Carlton, Chicago, is not just a hotel; it's an experience, crafted to leave a lasting impression of luxury and refinement on every guest who passes through its doors. It epitomizes the pinnacle of opulent lodging in Chicago.
Address:160 East Pearson Street At Water Tower Place
Rating:
Good
8.7
(77 Reviews)
Rooms:434
Price: From 390$
Culinary Heights: Expensive Hotels in Chicago with Gourmet Dining
For many travelers, the journey is as much about the culinary experiences as the destinations themselves. In Chicago, some of the most expensive hotels are also renowned for their exceptional dining options, offering guests the opportunity to embark on culinary adventures without ever leaving their accommodations. These hotels boast in-house restaurants led by celebrated chefs, presenting menus filled with innovative dishes that reflect the city’s diverse culinary scene. Luxurious settings, impeccable service, and a commitment to culinary excellence make these establishments a foodie’s dream. Let's delve into the hotels where gourmet dining takes center stage, enhancing the luxury lodging experience in Chicago.
Trump International Hotel & Tower Chicago
9.1
Good
(1198 Reviews)
+ 191 photos
Culinary excellence reaches new heights at the Trump International Hotel & Tower Chicago, where fine dining is an integral part of the luxury experience. Its signature restaurant, Terrace 16, not only offers stunning views of the city’s skyline and the Chicago River but also serves a delicious blend of American and global cuisine, with an emphasis on sustainable and local ingredients. The restaurant's vibrant atmosphere, coupled with its innovative dishes and exemplary service, ensures a memorable dining experience. Guests can indulge in culinary masterpieces, making their stay at one of Chicago’s most expensive hotels both a lavish and palatable affair.
Address:401 North Wabash Avenue
Rating:
Good
9.1
(1198 Reviews)
Rooms:339
Price: From 406$
The Peninsula Chicago Hotel
9.4
Good
(207 Reviews)
+ 269 photos
Rising majestically in the heart of Chicago is renowned for its unparalleled service, opulent design, and cutting-edge technology. This hotel redefines luxury in a modern context, offering rooms and suites equipped with intuitive technology, making everything from lighting to room service seamlessly customizable. The Peninsula Spa and the glass-enclosed swimming pool provide sanctuaries of relaxation, while the dining options, including the Michelin-starred Shanghai Terrace, offer culinary adventures. The Peninsula Chicago's commitment to excellence is palpable, providing an exquisite base from which to explore the vibrancy and dynamism of Chicago. It's a beacon of modern luxury, offering a sanctuary of sophistication in the bustling city.
Address:108 East Superior Street
Rating:
Good
9.4
(207 Reviews)
Rooms:257
Price: From 400$
The Langham Chicago Hotel
9.2
Good
(333 Reviews)
+ 157 photos
Located within the iconic Mies van der Rohe building, The Langham, Chicago combines architectural significance with interior sophistication. This hotel is a masterpiece of contemporary design, offering spacious, elegantly appointed rooms and suites that provide serene views of the cityscape and river. The Langham, Chicago takes the concept of luxury to new heights with its award-winning Chuan Spa, state-of-the-art fitness facilities, and exceptional dining options, including the visually striking afternoon tea service. Sustainability practices and innovative guest services underline the hotel's modern approach to luxury, ensuring a comfortable, memorable, and conscientious stay for all guests. It represents the forefront of contemporary luxury lodging in Chicago.