The Best Shopping Streets In the USA | Preferred Hotels (2024)

No great trip to any major city is complete without at least a few hours spent shopping. For the best of the best in the United States, head to four of the country’s top cities to stroll their famed shopping streets and come away with something special for yourself or your loved one.

From New York City’s urbane Fifth Avenue to Honolulu’s relaxed but no less luxurious Kalākaua Avenue, these four great shopping streets in the United States should be at the top of your travel to-do list.

Running along Central Park’s eastern edge, Fifth Avenue stretches for hundreds of blocks from Washington Square Park downtown all the way to Harlem in Manhattan’s far north. The best shopping, however, takes place in Midtown where hundreds of brands from mid-range to high-end can be found, including everything from Anthropologie to Versace. In between the dozens of boutiques, experience the city’s culture. Discover historic landmarks like The Empire State Building and the Flatiron Building and explore multiple museums including The Metropolitan Museum of Art and the Guggenheim Museum.

For an alternative to this high-traffic street – someplace that offers a more bohemian or innovative style of retail and fashion – head south to the city’s traditional home of the cool kids. In Greenwich Village, SoHo, Chelsea, and the Lower East Side, vibrant and hip clothing and homeware shops punctuate these old and charming neighborhoods with an array of restored rowhouses, warehouses, and merchant spaces.

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In just four Los Angeles-sized blocks, Rodeo Drive packs in an impressive roster of luxury labels. Peruse Tom Ford and Prada for high fashion, Rolex for the ultimate timepiece, Rimowa for all your luggage needs, and even Porsche if you’re seeking a new set of wheels. For everyone who can’t afford a watch the price of the average American’s salary, walking along this palm-lined Beverly Hills boulevard is still a magnetic experience and – who knows? - you might even spot a celebrity.

A less expensive, though no less luxurious alternative to Rodeo Drive, head to the quaint, village-like shopping center known as The Grove. There you’ll find a broader range of brands at a wider variety of prices. Shops include the likes of Coach, Apple, Le Labo, and Todd Snyder.

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When the nickname for a street is “The Magnificent Mile,” you know it must be good. And when it comes to shopping, Chicago’s North Michigan Avenue does not disappoint. Starting at the Chicago River in the south, Michigan Avenue runs north for 14 blocks before merging with another famed Chicago street, Lakeshore Drive. Within this narrow stretch of the city, shoppers are greeted by more than 450 retailers selling everything from apparel to cosmetics, jewelry, and toys. Brands run the gamut from Nike to Shinola, Cartier, and Away.

If a more low-key Chicago shopping destination is more your style, skip the Mile and journey deeper into some of the city’s best neighborhoods. Andersonville delivers a buffet of antique stores, furniture shops, cafes, and eateries, while Wicker Park offers a more bohemian vibe with its independent bookstores and vintage clothing shops.

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Beginning at the soft sands and crystal-clear waters of Waikiki Beach and the imposing Duke Kahanamoku surfing statue, shoppers move inland along Honolulu’s lushly landscaped main street toward the city’s towering beach hotels and the best shopping area in the Hawaiian Islands. Set in the main-floor retail spaces of seaside resorts, brands and stores such as Balenciaga, Burberry, Kate Spade, and Louis Vuitton are within walking distance of local favorites like Malie Organics and Reyn Spooner Hawaiian shirts.

Just off the Avenue, travelers and locals alike delight in the warm waters of the Pacific and indulge in tropical drinks, surf lessons, and sunbathing. Go the other way, however, and you’ll enter the real Honolulu where shops and boutiques cater to locals, and you can find everything from specialty Asian produce and foods to vintage Aloha shirts and island crafts.

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