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A potent concentration of famous retailers around Michigan Avenue and neighborhoods bursting with one-of-a-kind stores combine to make Chicago a shopper's paradise. Michigan Avenue's legendary Magnificent Mile lures thousands of avid shoppers every week. How often can you find Neiman Marcus, Macy's, Nordstrom, Saks Fifth Avenue, and Barneys New York within walking distance of one another? In recent years State Street has regained some of its former glory as well, with discount department stores sharing prime real estate with trendier clothing boutiques and the Block 37 retail development.
Neighborhood shopping areas, like fun-but-sophisticated Lincoln Park, eclectic Lakeview, and the hipster haven of Wicker Park/Bucktown, offer countless independent stores that cater to every desire, whether Prairie tyle furniture, cowboy boots, or outsider art. And there are countless smaller shopping enclaves within these neighborhoods that have concentrated clusters of antiques stores, home-furnishings shops, high-end boutiques, and other specialty stores. Those averse to paying retail won't have to venture far to unearth bargains on everything from fine jewelry to business attire. When it comes to shopping, this is one city that has it all.
Be forewarned that a steep 9.5% sales tax is added to all purchases in the city except groceries and prescription drugs. Neighborhood shops on the North Side, especially those in Wicker Park and Bucktown, tend to open late—around 11 or noon. Most stores, particularly those on North Michigan Avenue and the North Side, are open on Sunday, although this varies by type of business (galleries, for example, are often closed on Monday); where applicable, more information is provided at the beginning of each category.
Up-and-coming and established upscale women's clothing designers are artfully showcased in a space that's airy, bright, and uncluttered. The owners are pros at mixing fabrics and patterns, and putting unexpected pieces together with wonderful results. Refreshingly, staff put a premium on personable service, making you feel genuinely welcome whether you've come to drop a paycheck or just to browse.
This modern-day general store stocks trendy clothes and accessories at a wide range of price points. Pretty embroidered dresses, stylish denim, and handmade necklaces share space with quirky-cool gifts and home furnishings, ranging from candles and bath products to cheeseboards and cookbooks.
At this haute minimalist enclave, you'll find designers like Dries van Noten and Balenciaga, as well as shoes and accessories of a similar subtle elegance.
This boutique’s location in the historic Monadnock Building complements the vintage-inspired clothing, shoes, and accessories it carries.
Snap up canceled and overstocked designer clothes from the likes of Tahari and ABS at 40% to 70% discounts. Shipments come in several times a week, so there's always something new to try on. (Modest shoppers, take note: The dressing room is communal.)
The striking red facade of this flagship is unique and stylish, as is the merchandise inside, selected by fashion maven Ikram Goldman, known as the informal stylist to Michelle Obama. There are clothing and accessories from well-known designers like Azzedine Alaïa, Comme des Garcons, Gucci, and Valentino, as well as lesser-known brands like Muveil and Undercover. The Ikram sales staff is welcoming and knowledgeable and skilled at helping customers develop their style.
This well-stocked vintage shop is pure flashback fun. In addition to some fashion-forward pieces, Knee Deep specializes in apparel and accessories from the '20s to the '90s, with some vintage home furnishings and ephemera thrown in for good measure.
This boutique is a two-story treasure trove of well-curated must-haves for women from mindful, environment-friendly designers like Aviator Nation, Rag & Bone, and Ulla Johnson, all of which reflects the style of the trendy Southport Corridor.
There's a great selection of swimwear, workout clothes, and yoga gear here.
Once a mobile shop operating out of a 1976 Dodge RV, Lost Girls is now a brick-and-mortar store in Ukrainian Village (with an additional location in Logan Square). True to its theme of fun and adventure, you never know what you'll stumble upon. But you're sure to leave with a gem, be it a '50s cocktail dress or '70s beaded handbag. Stock is helpfully arranged by decade, so you can head straight for your favorite era.
This store is a must-hit for its fashion-forward collection by a cadre of hip women's designers like Eugenia Kim, Rachel Comey, and The Great. Customers from all over the city and well beyond come for adventurous to elegant styles at prices that don't get out of hand.
There's something for everyone at this spacious Ukrainian Village shop. Step inside for graphic two-piece sets from Compania Fantastica and cool knits from All:Row, as well as funky accessories such as Jenny Lemons earrings. Menswear by the likes of Native Youth and Rhythm plus a selection of children's clothes, housewares, and gift items round out the collection.
Robin Richman showcases interesting sculptural housewares and oversize vintage necklaces alongside pieces from lesser-known European labels and local clothes designers. Even if the rather lofty price point limits you to window shopping, the eclectic displays never disappoint.
Tops, jewelry, art prints, and books that celebrate Chicago-based Black makers and culture (sample t-shirt: "Harold's Chicken, Winter, & Sunsets") are at the heart of this shop, which also aims to facilitate community for local residents through events like a popular annual block party.
This is a truly curated local shopping and dining experience, created by guys-in-the-know Jim Wetzel and Lance Lawson. The clothing selection (focused on new and emerging brands) is the big draw but there are also wonderful home items, apothecary goods, inspired coffee table books, and all kinds of gift items. While you're here, you can grab a bite at The Lunchroom, the 40-seat breakfast, lunch, and weekend brunch restaurant. The Lunchbox features take-away sandwiches, baked goods, and quiches, along with a coffee bar, cold drinks, and curated wine bottles.
Friendly owner Lesley Timpe stocks her Humboldt Park boutique with fun accessories and vibrantly printed dresses and cropped tees in easy-wearing fabrics that manage to tick the boxes for both style and comfort. Some of the goods come from her own line, which shares the shop’s name.
Board of Trade types who like special attention and the perfect fit come to this legendary clothier for brands like Giorgio Armani and Ermenegildo Zegna. Home and office consultations are available.
This Wicker Park favorite is bursting at the seams with affordable styles for guys and girls. The accessories here, often even more fun than the clothing, may include vintage bow ties, Pendleton blankets, backpacks, and incredibly colorful jewelry. A room packed with vintage clothes hides down a creaky flight of stairs.
More than 300 local designers have showcased their work at this longtime favorite. Owners Shirley Kienitz and Jenny Stadler carry clothing, jewelry, home goods, and art at very reasonable prices. They also have occasional workshops.
Young trendsetters flock to this mini-empire for fashion-forward threads at easy-to-swallow prices. The flagship women's boutique shares a stretch of North Avenue with offshoot men's clothing and women's shoe stores. Check the website for other locations.
The French designer's famous takes on the classic white shirt sport hefty price tags, though they also show a careful attention to detail.
This bastion of conservative ready-to-wear fashion still sells boatloads of their classic 1837 navy blazer. But this one-stop shop for Oxfords and khakis also sneaks in bold colors.
The label once favored by the conservatively well dressed is now hot with lots of other people who can't get enough of its signature plaid on everything from bikinis to baby gear. Even the exterior of this stunning Mag Mile flagship features that tan-and-black plaid.
Ensconced in the Drake Hotel, this shop carries the complete line of Chanel products, including ready-to-wear, fragrances, and cosmetics.
The sportswear, softly tailored business attire, and dress clothes of this Italian great are gathered all under one roof.
An airy, two-floor space displays Armani's discreetly luxurious clothes and accessories. The store includes the top-priced Black Label line, considered a cut above the department store line.
Though the prices aren't for the faint of heart, there are some pieces here that will last a lifetime.
The well-heeled shop the Chicago flagship for suits, signature scarves, and leather accessories.
Men will find modern, well-cut suits with attention to tailoring, as well as other signature Boss clothing and accessories here.
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