Holiday Shopping Wonderlands

This holiday season, take a seat in a private lounge while a stylist brings clothes to you. Or go to a mall to shop among modern art exhibits and listen to a DJ spin tunes.

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To compete with online retailers, brick-and-mortar stores in Chicago are making shopping more of an experience, and for the holidays, they’ve upped their game. Their goal? To make tackling your gift list much more enjoyable than sitting in front of a computer screen. Before you order online, check out some of these fun shopping experiences in Chicago and the surrounding suburbs.

Sleek style

Buying cosmetics and perfume is a high-tech, hands-on experience at Michigan Avenue’s flagship Sephora, filled with iPad and Google Assistant stations that let you take beauty classes, experiment with products (both virtually and in real life) and then share your new look online. Shopping is like hanging out at a friend’s hip River North condo at Trunk Club, an appointment-only adult clothing store owned by Nordstrom. Start with a complementary cocktail or coffee at their bar until a stylist brings you to a private living room space. There, they’ll bring out clothes and offer fashion suggestions.

RH (Restoration Hardware) is a gorgeous space filled with cozy seating and the beloved 3 Arts Club Café, located in the indoor garden courtyard. Everything you see, eat or drink at RH–like fur pillows, stylish home decor, plush throws, or a nice bottle of wine—is for sale. The stunning design makes it a great place to bring guests for both lounging and relaxed holiday shopping.

Downtown Chicago’s newly opened and buzzed about AmazonGo stores let you buy gifts like made-in-Illinois foods, artisan chocolate or wine and “just walk out.” Here’s how the cashier-less stores work: scan the app when you walk in, and then cameras and sensors automatically scan what you take off the shelves. It charges you for what’s in your bag as you exit.

Family favorites

A December shopping trip to Macy’s State Street must begin with a peek at its animated outdoor holiday window displays. They’ve been a Chicago tradition for generations, dating back to when it was a Marshall Field’s store. Afterward, go inside and shop the eight-floor department store that encircles Macy’s 45-foot Great Tree. Snag gifts like Frango Mints (an old-school Chicago treat), Chicago sports team merchandise and Chicago-themed Christmas ornaments. Long line to pay? Not if you use Scan & Pay in the Macy’s app. Just scan your items, pay through the app, and then whip through the Scan & Pay service kiosks for security tag removal and shopping bags.

Parents whose children are American Girl Doll fans will love shopping in their two-level store in Water Tower Place. Besides doll and doll accessory shopping, the store contains a hair salon and restaurants where the staff caters to the children and their dolls. Go to the 7th floor of Water Tower Place to get fun stocking stuffers at Candyality. Check out the mannequins dressed in clothing made from candy wrappers, shop the big selection of retro candies (“Oh, I used to love those!”), and ask the cashier to tell you your “Candyscope”—what your candy choices say about your personality.

Pop-up markets

Unique, locally made products and a festive spirit make pop-up markets, both indoors and outdoors, some of the hottest shopping spots in Chicago. During the holidays, the granddaddy of all of them is Christkindlmarket. The long running German-theme market has three Chicago locations and one in west suburban Naperville.

Grab a bag of warm candied nuts coated with crispy cinnamon-sugar and walk along rows of stands selling all sorts of items, including German-made products like cuckoo clocks, beer steins and sparkly ornaments. It’s a tradition for visitors to drink Glühwein, served in collectible souvenir mugs that change each year.

Hear live music performances or DJs spinning tunes while snacking on Yvolina’s homemade tamales and shopping at the Pilsen Community Market. The market, in the gentrifying Pilsen neighborhood, teems with products by Latina artists, bakers, and produce makers. It’s held every other Sunday from mid-November through April at the Honky Tonk BBQ (try their bacon candy).

Check Do312 to find a listing of most 1- to 3-day independent holiday markets, like the One of a Kind Holiday Show at the Merchandise Mart that sells unique and eclectic work from 600 artists (December 6–9) and the Lincoln Park Zoo Holiday Market (November 27), set up among the zoo animals and 2.5 million Christmas lights.

Beyond the Loop

Modern art displays draw shoppers’ eyes at the Fashion Outlets of Chicago in Rosemont, a giant designer outlet mall near O’Hare International Airport. With free shuttles from the airport and luggage check in the mall, even a long layover is enough time to shop for discounted things like Lululemon yoga pants or Gucci shoes. The mall’s Santa HQ, done in partnership with HGTV, has free interactive kid-friendly features like an electronic naughty-or-nice meter. Rent motorized zoo animals at the Bitty Bee Safaris kiosk and slowly cruise around the mall. 

Everyone loves to shop at Abt, a gigantic, family-owned electronics store in Glenview. Besides sitting in recliners, watching TVs, and eating the fresh-from-the-oven chocolate chip cookies they hand out on Saturday and Sunday afternoons, the store has displays like an Olympic torch and one-of-a-kind spinning “TV windmill.” Play in a contraption that covers you in one giant soapy bubble, or stare at the giant fish tanks and dancing fountain while pondering your holiday purchase.

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