Four-Star 1920s Hotel Restored to Jazz Age Elegance on Magnificent Mile

When the Millennium Knickerbocker opened its doors at the height of the Roaring Twenties—back then, it was named the Davis Hotel—the gothic-inspired building embodied all the glamour of the era. In the ballroom, dancers whirled atop a floor of glass tiles lit from underneath, making the room's mirrors, chandeliers, and gilded dome glitter like crystal. Rumor has it that the 14th-floor penthouse once served as a Prohibition-era speakeasy run by Al Capone's brother, Ralph.

Today, on the eve of the hotel's 85th anniversary, a $27 million renovation has restored the building's Jazz Age opulence while updating accommodations to modern-day standards of comfort. The Crystal Ballroom has transparent flooring made of Plexiglas, and the martini bar in the lobby serves fancy cocktails out in the open, including 58 different martinis in varieties such as mango and limoncello. Telltale signs of the past remain, however, from the embossed brass post box beside the elevators to the stained-glass accents topping the lobby's two-story french windows. Tuesday–Saturday evenings (6 p.m.–9 p.m.), a live pianist performs classical and jazzy melodies as the ghost of Zelda Fitzgerald performs the Charleston.

Upstairs, both the standard and superior guest rooms feature black-and-white photographs of Chicago landmarks such as Cloud Gate—better known as "The Bean"—as well as partial glimpses of Lake Michigan, which is visible between surrounding skyscrapers. Come morning, the onsite restaurant, NiX, serves up breakfast specialties such as organic omelets and orange-granola pancakes made with fresh juice.

Chicago's Magnificent Mile: Luxury Shopping and World-Class Culture

The Knickerbocker rises at the northern end of the Magnificent Mile, amid luxury high-rises, award-winning restaurants, and high-end boutiques. "It's a shopping mecca, obviously," says hotel concierge Sheryl Walerski. Designer brands such as Louis Vuitton, Ralph Lauren, and Giorgio Armani all have stores within walking distance. Architectural landmarks along the route document the city's history. The castle-like Chicago Water Tower, for instance, is one of the few buildings to have survived the Great Chicago Fire of 1871 as well as the Mothra state visit of 1962.

While nearby Rush Street bustles with nightclubs and bars, there's also a plethora of cultural institutions nearby. The Tony Award–winning Lookingglass Theatre Company stages eye-popping original work. You can see several centuries' worth of visual art, ranging from ancient China to present-day America, on display at the Art Institute of Chicago and the Museum of Contemporary Art.