An Elegant Chicago Neighborhood With Old-World Charm Is A Timeless Destination For Upscale Shopping

Chicago is a city of neighborhoods. Composed of 77 distinctive communities, there are plenty of delightful little pockets to explore that would appeal to every traveler's desires. If direct lake access, a free zoo, and tree-lined beauty sounds up your alley, visit Lincoln Park — which also boasts a whimsical Wizard of Oz-themed park. If artsy vibes, culinary delights, and unique architecture strike your fancy, then you should head to the up-and-coming neighborhood of West Town.

However, if none of those sound quite right, but a place that exudes old-world elegance and high-end glam hits the mark, then Chicago's Gold Coast neighborhood is the ideal destination. Nestled in the Near North Side community — Chicago's oldest locale — the historic neighborhood glimmers as brilliantly as its name suggests. 

Dotted with high-end boutiques, posh restaurants, and storied hotels, its picturesque streets are perfect for a day of window shopping and embracing the timeless beauty of the city. If coming from out of state, fly into Chicago O'Hare International Airport — from there, rent a car or take public transit. When digging into this particular pocket of Chicago, you'll find a pocketful of gold.

Dating back to the 19th century, the Gold Coast neighborhood — originally named the Astor Street District after wealthy business magnate John Jacob Astor — is rich with history. Step back in time by strolling down the eponymous Astor Street, where you'll be exposed to the neighborhood's legacy-filled landmarks like the original Playboy Mansion on 1340 North State Parkway and the Charnley-Persky House on 1365 North Astor Street. Designed by Louis Sullivan and Frank Lloyd Wright in the late 1800s, the latter offers year-round tours of its interior, which showcases one of the earliest examples of modern architecture.

Nestled among the elegant homes that dot Astor Street, you'll find a magnificent row of Romanesque Revival homes (1316 to 1322 North Astor Street) built for Chicago real estate tycoon Potter Palmer. During the late 1800s, Palmer commissioned the construction of a number of opulent buildings in the city, including the Palmer House Hotel — an undeniably elegant icon in the heart of downtown Chicago. For a guided glimpse into the Gold Coast's glittering past, you can book a tour with Walk Chicago Tours. Available from May through October, the informative Gold Coast Walking Tour highlights the neighborhood's 19th-century mansions, landmarks, and Gilded Age lore.

Step back into the 21st century by exploring Gold Coast's contemporary shopping district on Oak Street. Lined with designer apparel stores like Chanel and Prada and upscale jewelers like Cartier and Harry Winston, you'll find yourself in a paradise of high-end stores. Even if you're not in the market for luxury items, it's an ideal street to window-shop, people-watch, and daydream. Bordering Gold Coast is The Magnificent Mile, an illustrious shopping destination packed with even more stores and attractions.

Complementing its elegant shops and homes, Gold Coast is home to plenty of posh restaurants for world-class dining, like 3 Arts Club Café at RH Chicago, a gorgeously appointed garden courtyard restaurant centered beneath a cascading crystal chandelier. Located on the third floor of the Waldorf-Astoria, Brass Tack expertly balances warm, welcoming vibes with a sophisticated ambiance, serving upscale American cuisine alongside stunning city views. If you're in pursuit of a nightcap, wander down to the second floor of the hotel and sip specialty cocktails in Bernard's speakeasy lounge. To sleep in style, book your stay at the Waldorf or venture to InterContinental Chicago Magnificent Mile, a grandiose hotel that glistens with one of America's largest indoor pools.