Best Old Hotels in Chicago for Historic Charm

We checked thousands of reviews on and to find the best hotels for your stay
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Jacob Smith

Updated: 07 September 2024 · 3 min

Step back in time and immerse yourself in the rich history of Chicago, where the city's skyline is punctuated by the elegant spires of old hotels that have stood the test of time. From the iconic Palmer House to the opulent Drake Hotel, Chicago's historic accommodations offer a glimpse into the past while providing modern comfort and luxury for discerning travelers. Each old hotel in Chicago encapsulates a bygone era, inviting guests to experience a stay imbued with nostalgia and timeless elegance.

Embark on a journey through the cobbled streets of Chicago's iconic neighborhoods, where old hotels serve as architectural gems that reflect the city's storied past. The intricate facades and grand interiors of these historic establishments offer a portal to a different era, where every corner whispers tales of famous guests and historic events. A stay in one of these old hotels in Chicago is not just a lodging experience; it's a chance to connect with the city's heritage and relive the glamour of bygone days.

Whether you are a history enthusiast, a luxury traveler, or a curious explorer, the old hotels in Chicago promise a stay like no other, where modern amenities seamlessly blend with the grandeur of yesteryears. Indulge in impeccable service, exquisite dining, and timeless elegance as you bask in the charm of these revered establishments that have been a cornerstone of Chicago's hospitality scene for generations. Discover the allure of old hotels in Chicago and create memories that bridge the gap between the past and the present.
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Our Top 6

(Sorted by rating & number of reviews)

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

Old Hotels in Chicago Heritage

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Chicago
Mar 23, 2026 - Mar 24, 2026

The Palmer House Hilton Hotel

7.5

Good

(969 Reviews)

+ 216 photos
The iconic Palmer House Hilton stands as a testament to Chicago's architectural and hospitality legacy. Steeped in history, this legendary hotel first opened its doors in 1871 and has hosted numerous dignitaries and celebrities over the years. With its ornate lobby, exquisite ballrooms, and luxurious accommodations, the Palmer House Hilton is a quintessential example of old-world charm in the very heart of Chicago.
Address: 17 East Monroe Street
Rating: Good 7.5 (969 Reviews)
Rooms: 1641
Price: From 89$

Hilton Chicago Hotel

7.7

Good

(1058 Reviews)

+ 347 photos
As one of the city's oldest and most renowned hotels, The Hilton Chicago stands as a testament to Chicago's grand hospitality tradition. Dating back to 1927, this historic hotel showcases a blend of neo-classical architecture and modern amenities, providing a sophisticated retreat for travelers. With its exquisite ballrooms, fine dining options, and proximity to iconic attractions like Millennium Park, The Hilton Chicago offers a quintessential experience of old-world charm in the lively heart of the Windy City.
Address: 720 South Michigan Avenue
Rating: Good 7.7 (1058 Reviews)
Rooms: 1544
Price: From 119$

Old Hotels in Chicago's Legacy

Immerse yourself in the storied past of Chicago through a selection of distinguished old hotels that capture the essence of the city's rich heritage. These revered establishments have withstood the test of time, offering guests a glimpse into a bygone era while providing modern comforts and unparalleled service.

The Blackstone, Autograph Collection Hotel

8.5

Good

(425 Reviews)

+ 229 photos
Located in the vibrant South Loop neighborhood, The Blackstone, Autograph Collection, is a historic gem that has been a beacon of elegance since 1910. Renowned for its stunning Beaux-Arts architecture and artistic legacy, this hotel has welcomed luminaries such as Al Capone and multiple U.S. presidents. The Blackstone perfectly encapsulates the old-world charm of Chicago with its sophisticated décor, upscale amenities, and a rich history that resonates through every corner.
Address: 636 South Michigan Avenue
Rating: Good 8.5 (425 Reviews)
Rooms: 335
Price: From 159$

The Drake Hotel

8.0

Good

(587 Reviews)

+ 227 photos
Nestled along the Magnificent Mile, The Drake Hotel exudes a timeless allure that harkens back to Chicago's golden era. Since 1920, this historic hotel has welcomed guests with its elegant ambiance, classic décor, and impeccable service. Offering stunning views of Lake Michigan and the city skyline, The Drake Hotel is a perfect blend of old-world sophistication and modern comfort.
Address: 140 East Walton Place
Rating: Good 8.0 (587 Reviews)
Rooms: 535
Price: From 149$

Warwick Allerton Chicago Hotel

7.6

Good

(7033 Reviews)

+ 214 photos
Situated in the heart of the Magnificent Mile, The Warwick Allerton Chicago is a symbol of timeless elegance and sophistication. Originally built in 1924, this historic hotel has been a beloved destination for travelers seeking a taste of old-world glamour. With its glamorous rooftop lounge, luxurious accommodations, and proximity to top attractions, The Warwick Allerton Chicago offers a memorable stay steeped in Chicago's rich history.
Address: 701 North Michigan Avenue
Rating: Good 7.6 (7033 Reviews)
Rooms: 443
Price: From 71$

Intercontinental Chicago Magnificent Mile, An Ihg Hotel

8.0

Good

(500 Reviews)

+ 345 photos
Perched along the Magnificent Mile, The InterContinental Chicago Magnificent Mile boasts a prime position in the city's historic downtown area. Originally constructed as the Medinah Athletic Club in 1929, this luxurious hotel seamlessly blends the opulence of yesteryears with modern conveniences. Guests can marvel at the hotel's stunning lobby adorned with ornate decorations and explore elegant guest rooms that offer panoramic views of the city and Lake Michigan.
Address: 505 North Michigan Avenue
Rating: Good 8.0 (500 Reviews)
Rooms: 792
Price: From 109$