We’ve compiled the best of the best in Chicago - browse our top choices for the top things to see or do during your stay.

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  • 1. 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

  • 2. 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

  • 3. AllSaints

    Near North | Clothing

    AllSaints’ immaculate Chicago outpost is a required stop for edgy, dark-hearted fashionistas and fashionistos alike—especially those looking...Read More

  • 4. Anne Fontaine

    Near North | Clothing

    The French designer's famous takes on the classic white shirt sport hefty price tags, though they also show a careful attention to detail. ...Read More

  • 5. 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

  • 6. 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

  • 7. Belmont Army

    Lakeview | Clothing

    Converse, Dr. Martens, and other familiar brands get mixed in with fatigues, flak jackets, skate gear, and faux-fur coats at Belmont Army. The...Read More

  • 8. Blake

    River North | Clothing

    A no-nonsense boutique without pomp, circumstance, or even signage, Blake displays clean-lined clothes in a pristine setting. You'll find designers...Read More

  • 9. Brooks Brothers

    Near North | Clothing

    This bastion of conservative ready-to-wear fashion still sells boatloads of their classic 1837 navy blazer. But this one-stop shop for Oxfords...Read More

  • 10. Burberry

    Near North | Clothing

    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...Read More

  • 11. 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

  • 12. Chanel Boutique

    Near North | Clothing

    Ensconced in the Drake Hotel, this shop carries the complete line of Chanel products, including ready-to-wear, fragrances, and cosmetics. ...Read More

  • 13. 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

  • 14. Ermenegildo Zegna

    Near North | Clothing

    The sportswear, softly tailored business attire, and dress clothes of this Italian great are gathered all under one roof. ...Read More

  • 15. 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

  • 16. Florodora

    Loop | Clothing

    This boutique’s location in the historic Monadnock Building complements the vintage-inspired clothing and accessories it carries. Just down...Read More

  • 17. Fox's

    Lincoln Park | Clothing

    Snap up canceled and overstocked designer clothes from the likes of Tahari and ABS at 40% to 70% discounts. Shipments come in several times...Read More

  • 18. G Boutique

    Bucktown | Clothing

    Here's an all-in-one stop for women planning on a little romance. G Boutique sells beautiful lingerie from brands such as Eberjey and Cosabella...Read More

  • 19. Giorgio Armani

    Near North | Clothing

    An airy, two-floor space displays Armani's discreetly luxurious clothes and accessories. The store includes the top-priced Black Label line...Read More

  • 20. Gucci

    Near North | Clothing

    Though the prices aren't for the faint of heart, there are some pieces here that will last a lifetime. ...Read More

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