Find something for everyone on your list (including yourself) at Chicago’s top boutiques, retail centers, and shopping district. Our guide to shopping in Chicago during the holidays has everything you need to find one-of-a-kind gifts, from handmade crafts to artisan chocolate to luxury goods and beyond. to Explore holiday markets, neighborhood boutiques, high-end showrooms, and more in Chicago.

The Magnificent Mile on Michigan Avenue

Magnificent Mile Chicago Shopping

900 North Michigan Shops
Located at the north end of The Magnificent Mile shopping district, the 900 North Michigan Shops is a chic indoor shopping destination with 70 luxury stores such as Gucci, St. Croix and Michael Kors, all anchored by a six-story flagship Bloomingdale’s.

The Shops at North Bridge
Spread throughout six city blocks, shoppers can explore 50 stores, such as BOSS Hugo Boss, Lucky Brand, MAC and more, as well as a flagship Nordstrom and 20 restaurants including the massive Italian emporium Eataly.

Water Tower Place
With more than 100 shops, including Macy’s and a flagship American Girl Place, this spectacular, eight-level mall offers an array of retail options across all price ranges (from American Eagle Outfitters and Abercrombie & Fitch to Pandora and Swarovski), as well as dining, spas and more.

State Street: Shopping Chicago’s Loop

Macy’s on State Street
A must-visit gem in Chicago, this nine-floor flagship offers up everything on your shopping list: perfume, jewelry, handbags, clothing, housewares, toys, and of course, Frango® chocolates. It is an anchor of the State Street shopping district and is particularly festive around the holidays with its famed window displays and 45-foot Great Tree. The architecturally rich building is a National Historic Landmark, and boasts the first restaurant in a department store, The Walnut Room, which opened in 1907.

Block 37

Block 37
This landmark development features exciting retailers such as Anthropologie, Disney Store, Sephora, and Zara, an AMC Dine-in Movie Theatre, Magnolia Bakery, and vibrant Latinicity Food Hall & Lounge, all in a beautiful five-story building. This shopping destination also touts direct access to the CTA Red Line and Blue Line ‘L’ trains.

Neighborhood shopping

This charming area is known for its diversity, especially when it comes to shopping. Forget chain stores; this Andersonville’s commercial district is lined with independent boutiques and specialty shops like antiques at Roost, women’s clothing at Milk Handmade, and local art at Andersonville Galleria.

Looking for hip gift ideas? Hit up one of Lakeview’s vibrant retail corridors, like North Broadway or the bustling Southport Corridor, where you’ll find vintage shops, esoteric book stores, alternative clothing boutiques, and offbeat home décor. Don’t miss Foursided for quirky gifts and work by local artists.


Lincoln Park
For independent boutiques and high-end retailers, stroll down Armitage Avenue for a day of shopping. From upscale pet accessories to sophisticated home décor stores to trendy fashion boutiques, this is the spot to shop for well-heeled gift recipients. Laudi Vidni, for instance, sells custom-made leather goods for a truly one-of-a-kind gift.

Lincoln Square
Old World charm abounds in this German neighborhood, where you’ll find quaint shops like Merz Apothecary and Timeless Toys. When you’re ready for a break from shopping, refuel in one of the cozy bistros or sausage shops.

Roscoe Village
This casual neighborhood offers a welcoming mix of shopping centered on Roscoe Street. From vintage clothing stores to unusual knick-knack shops to upscale baby clothing, you’ll find it all at this “village within a city.”


Wicker Park/Bucktown
Get an urban shopping fix in this stylish neighborhood, where high-end antique stores and fashion industry icons are sidled alongside bohemian boutiques and eclectic art galleries, all along North, Milwaukee, and Damen Avenues.

West Town
This eclectic community (it’s comprised of the West Town, Noble Square, Ukrainian Village, and East Village neighborhoods) offers up a mix of funky thrift stores and independent retailers along Division and Chicago Avenue. While around Grand Avenue, those with an eye for design should hit the furniture showrooms, antique shops, and architectural salvage warehouses for unique finds.

Holiday markets & shopping events

  • Christkindlmarket
    Deck the halls after a trip to this annual outdoor market, which celebrates the holiday season with German-American traditions. Buy ornate, hand-blown glass ornaments, gorgeous nutcrackers, charming cuckoo clocks, and other wooden handicrafts. You also can sip on hot, spiced wine, nosh on sausages and potato pancakes, and sample many other German holiday delicacies.
  • One of a Kind Show
    Peruse the handmade wares of more than 600 artists and makers at the mammoth Merchandise Mart. While you’re there, catch an exciting artist demonstration, watch a fashion show or even create something original at a crafting workshop.
  • Julmarknad
    Travel to Sweden — or as close as you’ll get to it in Chicago — with this annual Swedish American Museum festival, where shoppers can stock up on traditional handcrafts and delight in free performances, such as Nordic folk dancing and Swedish choir recitals.
  • Renegade Craft Fair
    Head over to the Bridgeport Art Center for this festive holiday market, where more than 100 independent designers and artisans will be showing off their handmade jewelry, one-of-a-kind clothing, funky accessories, unique stationery, and more.

Discount outlet malls near Chicago

Chicago Premium Outlets
With 120 outlet stores, such as Cole Haan and Armani, deal hunters will be in shopping paradise while scoring discounts up to 65 percent off.

Fashion Outlets of Chicago
Do some deal hunting at this retail complex, where stores like Aldo, Nike, and Bath & Body Works are interspersed between upscale bargain shops like Neiman Marcus Last Call and Saks Avenue Off 5th and luxury labels like Gucci and Prada.

Pleasant Prairie Premium Outlets
This retail outlet in Wisconsin promises 90 stores offering impressive savings. You’ll find everything from Banana Republic and Hugo Boss to J. Crew and Nike.