Where to Stay in Chicago: Historic Hotels

Often on our architectural walking tours, locals and tourists alike will ask me about the best Chicago hotels. Being a Chicago native, I cannot recommend from experience. Instead, I recommend from history. Here are some of the best historic hotels in Chicago. There where I would stay if given the excuse.

Photo Credit: Chicago Postcard Museum
Photo Credit: Chicago Postcard Museum

Maybe the Most Legendary of the Best Historic Hotels

At Chicago Detours, we try to promote the more positive and cultural aspects of Chicago history. But for those desiring the gangster fix, I’d recommend staying at the Renaissance Blackstone Hotel. The historic barber shop, which was eliminated during recent renovations (what were they thinking?), can be seen in the film “The Untouchables.” All sorts of politicians, from mob bosses, to senators, to presidents, are known for staying at this historic hotel and for dealings in its smoke-filled rooms. We credit the Blackstone Hotel for this term as the legendary location of the first “smoke-filled room” where Warren Harding was nominated to run for president.

Hotel architects Marshall & Fox designed the Blackstone for the Drake brothers, who were powerful figures in the American hotel industry. It opened in 1908 and got its name for Timothy B. Blackstone, the head of the Union Stockyards and several railroads. Our tour guests can find it just a few blocks south of where our 1893 World’s Fair Tour begins on Michigan Avenue.

Hollywood on the Mag Mile

The Drake brothers had Marshall & Fox build another one of the best historic hotels in Chicago – their namesake. The Drake Hotel opened on New Year’s Eve in 1920 as a high-society palace in the posh Gold Coast neighborhood. At the opposite end of Michigan Avenue from the Blackstone Hotel, one can get a taste of Hollywood glamour in the Cape Cod Room. You can still see where Marilyn Monroe and Joe DiMaggio came as giggling lovers and carved their initials into the wooden bar. I often recommend a visit by guests intrigued by the glamour of the Intercontinental at the end of our Historic Chicago Walking Bar Tour.

Many know the 20-foot tall, neon-pink letters as a fixture of the Chicago Lakeshore Drive skyline, but just recently they have been brought into 2014 with light purple LED lights. Today the Drake Hotel leads in green initiatives around the city and continues to host all manner of celebrities and dignitaries.

Photo Credit: Palmer House Hilton Hotel
Photo Credit: Palmer House Hilton Hotel

The Best Historic Hotel in Chicago

For the architecture and the art, on a staycation in Chicago I would go to the Palmer House Hilton Hotel. It’s my favorite of the best historic hotels in downtown. Often, I have had the pleasure of meeting friends and private tour guests in their opulent lobby. With Beaux-Arts frescoes on its ceiling, from which hang 24-karat gold chandeliers by Tiffany, the lobby speaks for a gentle era of leisure and luxury. On the mezzanine are cozy nooks to drink and watch the crowd gather and the stars line up to play. In the Empire Room, where the chandelier pictured here hangs, performers such as Frank Sinatra, Ella Fitzgerald and Liberace graced the stage.

The Great Chicago Fire destroyed Potter Palmer’s first hotel was destroyed in t. He’d built it as a wedding gift from Potter to his wife. The history of the hotel and a collection of its art and artifacts are on view at the Hotel Museum. I’d also recommend the Lockwood. There you can grab a drink before exploring the hotel or experience it from the aforementioned cozy nooks.

Even without the excuse of needing to stay the night, locals and tourist alike can enjoy these historic hotels. Simply remember to step inside and enjoy the interior architecture.

— Elizabeth Tieri, Chicago Detours Tour Guide


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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