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Apartment Number 9
Apartment Number 9 bills itself as the first menswear store in Chicago and the only local boutique that carries labels like Dries van Noten for men. You’ll also find such coveted labels as Red Wing, Canada Goose and Maison Margiela....
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Blake
You’ll need to be buzzed in to this vast, minimal store, which inhabits the historic Chicago Avenue Post Office. Owners Marilyn Blaszka and Dominic Marcheschi began showcasing their pricey, edgy womenswear here in 1984, and still stand out in Chicago...
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Ikram
Shopping fanatics visiting Chicago should make this venerable boutique their first stop. Often referred to as Chicago’s “first lady of fashion,” Ikram Goldman’s namesake store is a great source for top labels like Proenza Schouler, Rick Owens, Alexander McQueen, Bottega...
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Madison Hall
Occupying two storefronts on the ground floor of the Chicago Athletic Association Hotel, Madison Hall is the brainchild of Lance Lawson and Jim Wetzel, who also own the wonderful boutique Space519. Like the hotel, the shop is located within a...
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Moth
This petite boutique on Wicker Park’s main strip, which opened in late 2015, features a collection of carefully selected Scandinavian and Japanese items. Browse unique finds such as delicate white ceramics, heavy Samuji striped tees and organic cotton Aiayu linens....
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P. 45
One of the first high-end shops to open in Wicker Park, in 1997, this excellent boutique carries a well-edited range of women’s fashion including lightweight cotton cashmere tops and slinky Mason frocks in vivid red silk. “We like our clothes...
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Space519
Don’t be put off by Space519’s unlikely location on the top floor of a mall (sorry—a luxury shopping complex) on the Magnificent Mile. The ultrachic boutique is an absolute gem whether you’re shopping for yourself or seeking a gift to...
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The 900 Shops
This upscale complex houses over 70 shops, including Gucci, MaxMara, Church’s and Bloomingdale’s. Top stops for those with tots are Galt Toys and Galt Baby, located on level 5. Of course, you may have to drop into Teuscher chocolates, across...
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Virtu
This charming lifestyle boutique sells an eclectic selection of gifts including letterpress stationery, ceramics, paper products, textiles and even spices.
Chicago

Courtesy Madison Hall
Chicago’s robust shopping scene is spread out across the neighborhoods: you’ll find just about any international chain and luxury brand on the Magnificent Mile, trendy shops for up-and-coming labels and home goods in Wicker Park, and high-end boutiques in tony Gold Coast. And don’t disparage the malls, which are home to some excellent independent boutiques and practically a necessity in this blizzard-prone town.