Sitting pretty just north of downtown, along the Lake Michigan shoreline, lies Chicago’s swanky crown jewel, aka the Gold Coast. In this über wealthy enclave — often considered the Beverly Hills of Chicago — historic mansions perched on picture-perfect tree-lined streets commingle with the very best of everything Chicago has to offer in a cocoon of luxe virtually unrivaled by any other neighborhood in the country. Here, streets brim with well-heeled denizens popping out of Bentleys, Maybachs and chauffeured cars into a swarm of high-end designer boutiques, award-winning restaurants, and luxurious five-star hotels populating this famously luxury forward destination.

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The Gold Coast was the original home of Hugh Hefner’s Playboy Mansion and is now the go to hotspot for some of Chicago’s glitziest dining mainstays like Maple & Ash, Nico Osteria, or Gibsons, one of the most revered steakhouses in the city.

 

Also located on the Gold Coast is the Magnificent Mile, an iconic stretch of restaurants, shops, department stores and architecture that more than lives up to the grandeur implied in its moniker. As if this prestigious quadrant of the city hadn’t already soared to the headiest of heights, there can be little doubt that 900 North Michigan Shops confirms the Magnificent Mile’s status as the preeminent destination for shopping in the city. In this striking 450,000 square-feet lifestyle retail space, familiar names like Bloomingdales reside alongside luxury retailers like Gucci, MaxMara, Montblanc, BONOBOS, Sur La Table, and Aritzia. Shopping aside, a particular highlight of the 900 Shops is the 22,000-square-foot, chef-driven food emporium Aster Hall. After closing during the pandemic, this foodie fantasy has reopened albeit with certain COVID-related restrictions and modifications.

 

Finally, for the best accommodations in Chicago, you need not look beyond the borders of the Gold Coast. From the elegant modernity of the Viceroy and the Sofitel, to the regal sprawl of the Peninsula and famed Parisian cobblestone courtyard of the Waldorf Astoria, there is no better address in Chicago. In fact, one might call these addresses golden.