Chicago

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.

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  • 1. CB2

    Lincoln Park | Household Items/Furniture

    A concept store by furniture giant Crate&Barrel, CB2 got its start right here in Chicago. Expect bold basics for trendy urban abodes, all...Read More

  • 2. Jayson Home

    Lincoln Park | Household Items/Furniture

    Loaded with new and vintage European and American furnishings, this decor store carries the Mitchell Gold + Bob Williams line. Look for oversize...Read More

  • 3. Lori's Designer Shoes

    Lincoln Park | Shoes/Luggage/Leather Goods

    Owner Lori Andre's obsession with shoes takes her on biannual trips to Europe to scour for styles you won't likely see at department stores...Read More

  • 4. Myopic Books

    Wicker Park | Books/Stationery

    One of Chicago's largest used-book dealers carries more than 80,000 titles and buys books from the public on Friday evenings and all-day Saturday...Read More

  • 5. A New Leaf

    Lincoln Park | Flowers

    You'll find one of Chicago's best selections of fresh flowers here. Designed by architect Cynthia Weese, the breathtaking Wells Street store...Read More

  • 6. Akira

    Wicker Park | Clothing

    Young trendsetters flock to this mini-empire for fashion-forward threads at easy-to-swallow prices. The flagship women's boutique shares a stretch...Read More

  • 7. Alan Design Studio

    Bucktown | Household Items/Furniture

    The offerings at this design atelier, owned by a former feature-film set decorator, range from Victorian to mid-20th-century modern. There's...Read More

  • 8. Alcala's Western Wear

    Ukrainian Village | Clothing

    Alcala stocks more than 10,000 pairs of cowboy boots—many in exotic skins—for men, women, and children. Since it's in Ukrainian Village, it...Read More

  • 9. apartment number 9

    Bucktown | Clothing

    Siblings Amy and Sarah Blessing offer sisterly advice to guys on what styles best suit them. Their store, named for the Tammy Wynette song,...Read More

  • 10. Aroma Workshop

    Lincoln Park | Perfume/Cosmetics

    Customize lotions, massage oils, and bath salts with more than 150 essential and fragrance oils in this beauty boutique. The workshop makes...Read More

  • 11. Art Effect

    Lincoln Park | Clothing

    This modern-day general store stocks trendy clothes and accessories at approachable prices. Ella Moss tanks, Rich and Skinny jeans, and Alexis...Read More

  • 12. Asrai Garden

    Wicker Park | Flowers

    Although you'd be hard-pressed to find fresher blooms or more carefully constructed bouquets, this quirky boutique is more than a flower shop...Read More

  • 13. Barker & Meowsky

    Lincoln Park | Pets

    This "paw firm" carries great gifts for dogs, cats, and humans. There are beautiful bowls, plush beds, picture frames, treats, and even pet...Read More

  • 14. Bedside Manor

    Lincoln Park | Household Items/Furniture

    Dreamland is even more inviting with these handcrafted beds and lush designer linens, many of which come in interesting jacquard weaves or are...Read More

  • 15. Camelot Children's Kingdom

    Lincoln Park | Clothing

    This brightly colored boutique carries American and European clothing lines for babies and children up to age 12. Some of the brands you'll...Read More

  • 16. City Soles

    Bucktown | Shoes/Luggage/Leather Goods

    This on-trend shop is a mecca for shoe lovers. There's a vast selection of edgy men's and women's footwear from Coclico, Chie Mihara, Sorel...Read More

  • 17. Crate&Barrel

    Lincoln Park | Household Items/Furniture

    There are plenty of "oohs" and "aahs" throughout the three floors of stylish home furnishings and kitchenware at Crate&Barrel's flagship...Read More

  • 18. Cynthia Rowley

    Bucktown | Clothing

    Chicago-area native Cynthia Rowley fills her Bucktown store with the exuberant, well-priced dresses, separates, and accessories that have made...Read More

  • 19. Dusty Groove

    Wicker Park | Music Stores

    The retail outlet of a massive online business, Dusty Groove stocks an enormous collection of older jazz, funk, soul, and blues in both LP and...Read More

  • 20. Eskell

    Wicker Park | Clothing

    Although this women’s boutique can be a bit on the pricey side, Eskell’s selection of clothing, jewelry, fragrances, and assorted home goods...Read More

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