Best Old Hotels in Downtown Chicago

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Nestled amidst the bustling streets and glittering skyscrapers of downtown Chicago lies a treasure trove of history and elegance - the old hotels that have stood the test of time. Stepping into these iconic establishments is like stepping back in time, where each creak of the floorboards and every intricate detail tells a story of a bygone era. From the historic architecture to the timeless charm, these hotels offer a glimpse into the rich heritage of Chicago's hospitality scene.

Travelers seeking a unique and memorable experience will find solace in the refined ambiance and classic charm of these old hotels. Whether you're drawn to the opulent grandeur of a historic ballroom or the cozy intimacy of a vintage cocktail lounge, each establishment boasts its own distinctive character and allure. Immerse yourself in the art deco glamour of the Roaring Twenties or bask in the classic elegance of the Victorian era - a stay in these old hotels is a journey through the annals of Chicago's past.

Beyond the exquisite decor and luxurious amenities, the old hotels in downtown Chicago offer a gateway to the city's vibrant cultural tapestry. Located in the very heart of the action, guests can easily explore renowned attractions, upscale boutiques, and world-class dining establishments just steps away from their elegant accommodations. Whether you're a history buff, a connoisseur of vintage aesthetics, or simply a traveler craving a touch of nostalgia, a stay in one of these old hotels is a quintessential Chicago experience not to be missed.

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Our Top 6

(Sorted by rating & number of reviews)

1. Intercontinental Chicago Magnificent Mile, An Ihg Hotel
2. The Drake Hotel
3. The Palmer House Hilton
4. Warwick Allerton Chicago
5. The Ritz-Carlton, Chicago Hotel
6. The Blackstone, Autograph Collection

Timeless Grandeur: Old Hotels in Downtown Chicago

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Chicago
Mar 06, 2026 - Mar 07, 2026

Intercontinental Chicago Magnificent Mile, An Ihg Hotel

8.0

Good

(542 Reviews)

+ 344 photos
Originally constructed as the Medinah Athletic Club in 1929, the InterContinental Chicago Magnificent Mile is a true icon of vintage glamour in downtown Chicago. The hotel's opulent interiors, including the stunning Grand Ballroom with its Moorish-inspired decor, pay tribute to the lavish social scene of the early 20th century. With its historic charm, modern amenities, and prime location on the Magnificent Mile, the InterContinental Chicago Magnificent Mile offers guests a luxurious and immersive experience in the heart of the city.
Address: 505 North Michigan Avenue
Rating: Good 8.0 (542 Reviews)
Rooms: 792
Price: From 109$

The Drake Hotel

7.9

Good

(574 Reviews)

+ 227 photos
Perched along the Magnificent Mile, The Drake is a legendary Chicago institution known for its timeless elegance and historic significance. Since its opening in 1920, this iconic hotel has played host to dignitaries, celebrities, and discerning travelers seeking a taste of luxury. The lavish interiors, reminiscent of a bygone era, offer guests a glimpse into Chicago's storied past, while the impeccable service ensures a truly unforgettable stay.
Address: 140 East Walton Place
Rating: Good 7.9 (574 Reviews)
Rooms: 535
Price: From 133$

Classic Elegance: Old Hotels in Downtown Chicago

Step into a world of classic elegance and refined luxury with our selection of old hotels in downtown Chicago. These timeless establishments exude a sense of grace and sophistication, inviting guests to experience the grandeur of a bygone era. From exquisite decor to impeccable service, each hotel in this section radiates a sense of old-world charm that is sure to captivate discerning travelers.

The Palmer House Hilton

7.5

Good

(925 Reviews)

+ 216 photos
Located in the lively heart of the Loop, the Palmer House stands as a testament to Chicago's architectural and hospitality legacy. Established in 1871, this iconic hotel blends modern amenities seamlessly with its historic roots, offering guests a luxurious and authentic experience. The ornate lobby, adorned with crystal chandeliers and marble columns, transports visitors to a bygone era of opulence and sophistication.
Address: 17 East Monroe Street
Rating: Good 7.5 (925 Reviews)
Rooms: 1641
Price: From 89$

Warwick Allerton Chicago

7.4

Good

(6119 Reviews)

+ 214 photos
Originally opened in 1924, The Warwick Allerton - Chicago is a stunning example of Art Deco architecture in downtown Chicago. Boasting an elegant facade and meticulously restored interiors, this historic hotel exudes a sense of timeless glamour and sophistication. The Art Deco details, from the lobby's intricate moldings to the vintage light fixtures, immerse guests in a bygone era of elegance and style.
Address: 701 N Michigan Ave
Rating: Good 7.4 (6119 Reviews)
Rooms: 443
Price: From 92$

Vintage Chic: Old Hotels in Downtown Chicago

Embrace the allure of vintage chic with our curated selection of old hotels in downtown Chicago. These charming establishments blend old-world charm with modern comforts, creating a unique ambiance that appeals to travelers with a keen eye for nostalgia. From classic furnishings to restored architectural details, each hotel in this section exudes a sense of character and sophistication that sets them apart from the modern hospitality landscape.

The Ritz-Carlton, Chicago Hotel

8.7

Good

(77 Reviews)

+ 263 photos
Located atop the iconic Water Tower Place, The Ritz-Carlton, Chicago seamlessly blends modern luxury with Jazz Age chic. The hotel's sleek design and sophisticated decor pay tribute to the era's opulence and style, offering guests a refined and elegant retreat in the heart of downtown. With panoramic views of the city skyline and a commitment to impeccable service, The Ritz-Carlton, Chicago captures the essence of the Jazz Age while providing a contemporary and luxurious experience.
Address: 160 East Pearson Street At Water Tower Place
Rating: Good 8.7 (77 Reviews)
Rooms: 434
Price: From 390$

The Blackstone, Autograph Collection

8.5

Good

(469 Reviews)

+ 229 photos
A true icon of Chicago's architectural landscape, The Blackstone has been a beacon of luxury and refinement since its opening in 1910. With its Beaux-Arts design and Art Deco interiors, this historic hotel exudes timeless elegance and sophistication. From its legendary bar to its meticulously designed rooms, every aspect of The Blackstone speaks to a bygone era of grace and opulence, making it a standout among old hotels in downtown Chicago.
Address: 636 South Michigan Avenue
Rating: Good 8.5 (469 Reviews)
Rooms: 335
Price: From 159$

Historic Opulence: Old Hotels in Downtown Chicago

Experience the grandeur of historic opulence with our selection of old hotels in downtown Chicago. These distinguished establishments bring together luxury, history, and architectural splendor to create an unforgettable lodging experience. From elaborate facades to exquisite interiors, each hotel in this section embodies the essence of old-world hospitality, offering guests a glimpse into Chicago's illustrious past.

Art Deco Splendor: Old Hotels in Downtown Chicago

Immerse yourself in the vibrant world of Art Deco splendor with our selection of old hotels in downtown Chicago. These iconic establishments showcase the striking architectural style of the early 20th century, offering guests a glimpse into a glamorous era of design and sophistication. From geometric motifs to sleek lines, each hotel in this section epitomizes the timeless allure of Art Deco in the lively heart of the Windy City.

Jazz Age Chic: Old Hotels in Downtown Chicago

Transport yourself to the vibrant era of the Jazz Age with our selection of old hotels in downtown Chicago that embody the spirit of this iconic period. These establishments pay homage to the roaring 1920s and 1930s, offering guests a taste of the glitz, glamour, and excitement that defined the Jazz Age. From swanky lounges to stylish suites, each hotel in this section channels the energy and sophistication of Chicago's legendary Jazz Age scene.

Vintage Glamour: Old Hotels in Downtown Chicago

Savor the allure of vintage glamour with our selection of old hotels in downtown Chicago that epitomize the height of sophistication from decades past. These historic establishments evoke a sense of nostalgia and refinement, inviting guests to indulge in a bygone era of elegance and grace. From ornate ballrooms to polished woodwork, each hotel in this section exudes a sense of vintage glamour that transcends time, making for an unforgettable stay in the Windy City.