Find something for everyone on your list (including yourself) at Chicago’s top boutiques, retail centers, and shopping districts. 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. Explore holiday markets, neighborhood boutiques, high-end showrooms, and more in Chicago.

Holiday markets and shopping events


This quintessential Chicago Christmas market celebrates the holiday season with German-American traditions. Find 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 500 artists and makers inside THE MART in River North. Discover thousands of handmade goods, including accessories, gourmet items, paintings, ceramics, home goods, holiday decor, jewelry, and beyond. While you’re there, catch an artist demonstration, watch a fashion show, or even create something original at a crafting workshop.

Pre-Kwanzaa Marketplace
Enjoy shopping, food, workshops, dancing, raffles, and more at this celebratory market hosted by Africa International House. The free event honors the Kwanzaa principle of ujamaa, or cooperative economics.

Renegade Craft Fair
Head over to the Morgan Manufacturing event space in the West Loop for this festive holiday market. More than 170 curated independent designers and artisans will be showing off their handmade jewelry, one-of-a-kind clothing, funky accessories, unique stationery, and more.

Find more holiday markets with unique gift options all around Chicago.

The Magnificent Mile on Michigan Avenue

Clayton Hauck for Choose Chicago

The Magnificent Mile is one of the most famous shopping areas in the world — home to a dizzying array of popular stores, restaurants, and attractions all on one iconic street. During the holidays, the street’s more than 200 trees are covered with millions of twinkling lights for a festive feel.

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, Aritzia, 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, White House Black Market, MAC Cosmetics, and more, as well as a flagship Nordstrom and 20 restaurants including the massive Italian emporium Eataly.

Water Tower Place
With nearly 100 shops, including 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 Aéropostale to Sephora and Lacoste— as well as dining, spas, Broadway Playhouse, and more.

Check out our full guide to shopping on The Magnificent Mile.

State Street: Shopping Chicago’s Loop

Chicago’s State Street is a one-stop spot for some of the city’s best shopping, with blocks on blocks of modern malls, historic department stores, specialty shops, bargain options, and more. Plus, it’s home to Macy’s on State Street, an iconic Christmas destination.

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. An anchor of the State Street shopping district, the department store 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
This landmark development features exciting retailers such as Anthropologie, Sephora, and Zara, along with plenty of dining options like an AMC Dine-in Movie Theatre, Magnolia Bakery, and The Dearborn, all in one modern five-story building. This shopping destination also touts direct access to the CTA Red Line and Blue Line ‘L’ trains.

Find more in our shopping guide to Chicago’s State Street district.

Neighborhood shopping

Chicago’s many neighborhoods are filled with charming boutiques, bookstores, gift shops, and more with one-of-a-kind gifts you won’t find anywhere else. Check out some of our favorite area’s for holiday shopping.

This charming area is known for its diversity, especially when it comes to shopping. Forget chain stores — Andersonville’s commercial district is lined with independent boutiques and specialty shops like Chicago souvenirs at Transit Tees, 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, low-key bookstores, alternative clothing boutiques, and offbeat home décor. Don’t miss Foursided for quirky gifts and work by local artists and Unabridged Bookstore for a curated literary selection.


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.

Hyde Park
This historic community has a bustling, tight-knit feel thanks to the nearby University of Chicago campus. Find the perfect gift at unique shops like Toys Et Cetera’s, 57th Street Books, or The Silver Room.

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.” Local favorites include Shangri-La Vintage, Bazar women’s boutique, and Twinkle Twinkle Little One.


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.

Lincoln Square
Old World charm abounds in this tiny neighborhood, where you’ll find nods to the area’s German heritage alongside modern shops and restaurants. Make time to stop into 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.

Discount outlet malls near Chicago

Snag great deals at these outlets malls in the Chicagoland area.

Fashion Outlets of Chicago
Do some deal hunting at this retail complex, where stores like Aldo, the Nike Factory Store, and Bath & Body Works are interspersed between upscale bargain shops like Nordstrom Rack and Saks OFF 5TH, as well as luxury labels like Gucci and Prada.

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.