Where is the best Chicago shopping?

Answers from Our Experts (4)

Until you’ve walked the length of Chicago’s Magnificent Mile, you won’t really know just how huge of a shopping destination this section of Michigan Avenue is. Head north on Michigan to peruse the shops between the Chicago River and Oak Street, and your closet will lack for nothing. From reliable chains like Gap, Guess and Aldo; to high-end department stores such as Neiman Marcus and Bloomingdale’s; to niche shops like the Apple Store and Niketown, you’re hard-pressed to go home empty-handed.
If you’re searching for something homegrown, break away to culturally rich neighborhoods such as Wicker Park, where you can often buy local designer goods at boutiques such as Eskell or vintage everything at Lenny & Me.
When it comes to shopping for clothes, young girls might prefer to stick to the Mag Mile to hit American Girl Place in Water Tower Place mall to outfit their dolls. Aside from the new wardrobe, girls can pamper their Samanthas and Kayas with a cut at the doll hair salon, afternoon tea at the café and family portraits at the photo studio — all are available at the massive Chicago shop, the company’s first flagship store.

Kim Atkinson

Most everyone who comes to Chicago to shop will make Michigan Avenue and its scores of big name department stores and shops their first stop—and rightly so. Along this stretch of skyscraper-lined street you'll find familiar names such as Saks Fifth Avenue, Tiffany & Co. and Nordstrom. The compact nature of the Miracle Mile means you'll have an easy time finding whatever it is you're looking for (fashion, shoes, toys, cosmetics, you name it), without having to venture far. But do so—say, to one of Chicago's charming neighborhoods such as Wicker Park, Bucktown, Lincoln Park or the West Loop—and you'll find boutiques and fashion labels you won't find elsewhere.

Caroline Patek

Although it's no Fifth Avenue or Rodeo Drive, Chicago's Michigan Avenue certainly holds its own in terms of shopping. The city's Magnificent Mile is home to major high-end brands such as Chanel, Escada, Max Mara and Burberry, and trendy spots like Topshop and All Saints are sprinkled in as well. What's great about Michigan Avenue is the smaller side streets that also boast fan favorites such as Tory Burch, Tod's, Prada and Barney's. 

Head to Lincoln Park for more retail therapy along Halsted Avenue — you'll find Club Monaco, Blue Mercury, BCBG and more. Eateries along the stretch such as Toast and Cafe Ba Ba Reeba are great when you need to take a break too.

The Bucktown neighborhood has developed into its own shopping destination in recent years. Walk down Damen Avenue to shop the racks at Nanette Lepore, Marc by Marc Jacobs, Intermix and Scoop NYC. 

Lauren Viera

The obvious answer? The Magnificent Mile, which is lined with every major department store from Nordstrom to Neiman Marcus, as well as luxury retailers (Burberry, Louis Vuitton) and international imports (Top Shop, AllSaints). At its north end, the Mag Mile spills over into Oak Street and the Gold Coast, home to more luxury shopping such as Prada and Paul Stewart, as well as renown Stateside and North American institutions ranging from Urban Outfitters to Lululemon.

For boutique shopping, your best destination is hipster haven Wicker Park, extending north on Damen Avenue (Marc by Marc Jacobs, Club Monoco) and south to the Division Strip, packed with unique Chicago retailers. Loads of fun cafes and bars make this neighborhood great for a long afternoon of shopping till you (or your credit limit) drop.

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