Find the best shopping in Chicago, no matter who’s on your holiday gift list, with this year’s holiday shopping guide. From outlet malls in the Chicago suburbs to shopping in downtown Chicago, there’s plenty to find for label lovers and bargain hunters alike.
Michigan Avenue “The Magnificent Mile”
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, in addition to one of the best-known department stores in the world: 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, Joe’s Stone Crab, and The Purple Pig — all in the expansive North Bridge District.
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.
This landmark development features exciting retailers such as Sephora and Zara, restaurants and specialty food stores like Latinicity and Magnolia Bakery, plus The Chicago Design Museum, all in a beautiful five-story atrium. This shopping destination also touts direct access to the CTA Red Line and Blue Line ‘L’ trains.
Home to the Swedish American Museum and one of the city’s largest LGBTQ communities, this area is known for its diversity, especially when it comes to shopping. Forget chain stores; this neighborhood’s commercial district is lined with independent boutiques and specialty shops like Roost, Milk Handmade, and Andersonville Galleria.
Looking for hip gift ideas? Hit up one of Lakeview’s vibrant commercial districts, located along Belmont Avenue, Lincoln Avenue, Southport Avenue, Clark Street, Halsted Street, or Broadway Street, where you’ll find vintage shops, esoteric book stores, alternative clothing boutiques, and offbeat home décor.
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.
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.
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.”
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.
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.
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.
Holiday markets & shopping events
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.
- Randolph Street’s Holiday Market
Antique shoppers will love this one-of-a-kind market, where fabulous finds are at every beautifully curated corner. Browse memorable keepsakes, timeless antiques, vintage furs, estate jewelry and more at this posh event.
- 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.
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.