The Windy City will sweep you away with its fascinating history that spans legendary American gangsters, inspiring architects, and culture-shifting blues musicians. Stay in an institution that shaped the city's 1920s and 1930s with one of the most historic hotels in Chicago, the Millennium Knickerbocker. Opened in 1927, this grand hotel was at the center of Chicago's Prohibition past, operating as a speakeasy associated with Al Capone himself. Discover vestiges of this notorious era throughout the hotel's updated interiors and uncover more historical gems in Chicago's steely streets.

 

Becoming the Second City: Chicago in the 1920s and 1930s

Chicago earned a gangster reputation in the 1920s and 1930s with legendary mafia bosses like Al Capone, or Scarface, and the illicit alcohol production during the prohibition (1920-1933). Epitomized in movies like The Untouchables and Public Enemies, Chicago's crime scene boomed with widespread corruption under the impoverishing effects of the Great Depression. While the prohibition's repeal and the FBI did much to end the Gangster Era, its iconic landmarks remain. These include the Biograph Theatre, where "Public Enemy Number One," John Dillinger, was foiled, and the Holy Name Cathedral, marked by several North Side Gang bullets.

 

 

 
Mobs made their money in speakeasies across Chicago, venues illegally selling alcohol during the prohibition until 1933. Some of these spots exist today, including Butch McGuire's (once Kelly's Pleasure Palace), noted as one of the city's first pubs to serve Guinness. The Exchequer Restaurant & Pub is another noted spot, then known as the 226 Club. Capone would have frequented this speakeasy and often fled through now-covered underground tunnels.

 
While Chicago's dark past remains engrossing, the music scene also developed alongside it. Former mafia-run clubs like the Green Mill remain as glamorous now as in their jazzy heyday. Chicago owes its musical heritage to the jazz that flourished in the 1920s when prohibition described it as the "devil's music." Gangsters and jazz went hand in hand with legendary musicians performing at speakeasies, cocktail bars, and gin houses. The aesthetic of the period is represented at Millennium Knickerbocker's very own Crystal Ballroom, where hedonistic flappers would perform the Charleston to swinging jazz tunes beneath the elaborate, 25-foot gilded dome ceiling.

 

Millennium Knickerbocker: A Chicago institution

Launched during the Roaring Twenties as the Davis Hotel along what is now known as the Magnificent Mile, the Millennium Knickerbocker was designed by the noted Chicago architects Rissman & Hirschfield. Known for their luxury high-rises along Lake Shore Drive, the Davis (Millennium Knickerbocker) was their most lavish work to date. It combined Gothic Revival, and Beaux-Arts touches to become Chicago's go-to hotel. Its biggest draw was its lavish Georgian-style Crystal Ballroom, the only illuminated dancefloor in the city and a hub for socialites, celebrities, and even the mafia. The Crystal Ballroom remains as impressive as ever today and a choice wedding destination for Art Deco fans.


The Knickerbocker Hotel's Penthouse earned a notorious reputation as the location of a secret casino operated by Al Capone's older brother Ralph Capone. The Knickerbocker's renovation revealed hidden passageways thought to be linked to this illicit activity. The hotel continued to figure in Chicago's history, hosting touring musicians and politicians, from the Rolling Stones to JFK. The hotel changed names in the 1970s to the Playboy Towers Hotel under Hugh Hefner, sparking a new decade of history hosting starlets and celebrities.

 
With a wide range of rooms and suites, each maintaining its historic integrity yet updated for modern tastes, Millennium Knickerbocker is an ideal choice for families, friends, and couples. Antiques and ornate chandeliers don the impressive lobby, while guest rooms maintain elegant bathrooms, tufted headboards, and warming, neutral color schemes for an inviting experience. Street views complete the experience across most guest suites.

 

 

 

Explore Chicago's history

History starts at the Knickerbocker Hotel with its vintage, neotraditional rooms and lounges steeped in over a century of history. Whether sipping on one of over 50 types of martinis in the Knickerbocker's 1920s-style Martini Bar or enjoying an afternoon tea in the Library Tea Room, it feels like you're immersed in history. The Knickerbocker's location provides easy access to more of Chicago's historic buildings and attractions. Follow the Magnificent Mile south from your hotel's front door to discover architectural landmarks like the Wrigley Building, Chicago Water Tower, and Tribune Tower. Chicago historical tours all traverse this important street known for its towering skyscrapers and Beaux-Arts architecture.


Take a diversion to visit the Museum of Contemporary Art, just east of the Magnificent Mile. Chicago History Museum in Lincoln Park, located on the North Side and accessible via Lake Shore Drive, is also worth a visit. You'll take in familiar 1920s glamour with Chicago historic buildings en route before learning about the city's illustrious history within the museum's grounds.


For a deeper dive into the thrilling world of Chicago's Gangster Era, book gangster tours in Chicago. The Untouchable Tours’ Chicago Original Gangster Tour takes in the sites of Capone and Dillinger with immersive guides drawing you right into the 1920s. You'll learn all about the famous mafia haunts, the prohibition, and how speakeasies worked. You'll hear detailed, family-friendly exploits from an air-conditioned bus before reaching noted mob sites and haunts. As an associated site with its own Capone tales, tours depart right from the Knickerbocker Hotel.

 

Experience the thrills of Chicago history with a Millennium Knickerbocker package

Combine your stay at the famed Millennium Knickerbocker with an Untouchables Tours ticket. Covering 2 guests, you can take a deeper dive into the Knickerbocker's role in the Roaring Twenties, mob history, and the illicit prohibition-era alcohol trade. Book your tickets for your stay at one of the most historic hotels in Chicago for a captivating day out with family and friends.