TRAVEL + LEISURE | A Chicago Time Staycation

SO MANY THINGS TO LOVE ABOUT THIS HISTORICAL BEAUTY Millennium Knickerbocker Chicago While many know Green Mill Cocktail Lounge was a spot favorited by mobster Al Capone in the 1920’s, Chicagoans may be surprised to learn the history of another destination frequented by notable personalities from the past century.

Located in Streeterville just off of Michigan Avenue, the historic property now home to Millennium Knickerbocker Chicago has served lively purposes since its construction in 1927. Al Capone’s brother once ran a casino on the Penthouse Floor, and in the ’70s, the property had a stint as the Playboy Towers. The building housed the editorial and business offices of Playboy. The hotel has also hosted such luminaries as John F. Kennedy, Richard Nixon and the Rolling Stones.

Today, locals and visitors can sip on a dirty martini at Knickerbocker Chicago’s 1920’s-inspired martini bar and envision the lives of those who once walked the halls. The overall design of the hotel embodies “Old Chicago” with unique accents including ornate chandeliers and vintage furniture in the lobby. The hotel’s Crystal Ballroom, covered by a gold-gilded domed ceiling, exemplifies the design from the glamorous Roaring Twenties.

For guests staying at the hotel, the property is conveniently located near the shops on Michigan Avenue, 360 Chicago Observation Deck at John Hancock and the Museum of Contemporary Art. During the summer months, guests can easily walk to Oak Street Beach or Millennium Park to experience the various outdoor concerts and festivals.

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