Holiday Shopping Experiences

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.


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. From the Magnificent Mile to pop-up markets, Illinois Makers and other quaint shopping experiences beyond the city, read on to discover the best ways to enjoy the holiday shopping season.

  • Magnificent Mile + Macy's

    Big City Shopping

    Stroll the sparkling Mag Mile, marvel at Macy's animated holiday window displays and be sure to take a break at the new Starbucks Reserve Roastery or one of the many holiday pop-up bars.

Sleek Style

The Magnificent Mile

If you're looking to get all your holiday shopping sorted in one convenient stretch, look no further than Chicago's Magnificent Mile. Dining, lodging and entertainment combine with world-class shopping that includes flagship retailers and department stores with all your favorite brands. Nike, Lululemon, Gucci, Hugo Boss, Patagonia, Bloomingdales, Sephora, MAC, Apple, Pandora, Cartier and literally EVERYTHING in between. And when you've shopped till you dropped at Water Tower Place relax by the Historic Water Tower while you plan your next stop. Check out the details below for more information on select stores that truly transform the in-person shopping experience.

    • Buying cosmetics and perfume is a high-tech, hands-on experience at Michigan Avenue’s flagship Sephora, filled with iPad stations that let you take beauty classes, experiment with products 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 complimentary 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. Everything you see, eat or drink at RH–like 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.

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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.

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Macy's Holiday Windows

Take a Break

Let's be honest, shopping is thirsty work. You've earned a break, so make it a good one by visiting a holiday pop-up bar for a celebratory beverage.

    • If you're seeking energy for the final stretch, look no further than Starbucks Reserve Roastery for all your caffeine-related needs. The largest Starbucks location in the world, this four-story shrine to coffee also features a full kitchen/bakery and mixologist-crafted beverages.
  • Locally made products & festive spirit

    Pop-up Markets

    Locally made products and a festive spirit make pop-up markets, both indoors and outdoors, some of the hottest shopping spots in Chicago.

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 will have two Chicago locations this year; one in the Loop and one in Wrigleyville. 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 2–5).

  • Discount Outlets and Charming Main Streets

    Beyond the Loop

    While Chicago is an epicenter for a wide variety of holiday shopping, there are plenty of other spots throughout the state to satisfy your gift-buying needs.

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.

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.

If the bright lights of big cities and designer brands aren't really your cup of tea, charming Main Street Galena is sure to fulfill your needs. Boasting half a mile of more than 125 independently owned shops and restaurants, Galena's Main Street is the perfect shopping destination for unique gifts and one-of-a-kind experiences. From candy and ice cream shops to spas, wine tasting and amazing dining options, the Galena shopping experience is downright surreal because it all happens along an 1800s street with original buildings and no routine ‘brand’ shops. You'll find yourself crossing off your list without the draining neon lighting and loud music. Visitors to the Helluva Half Mile, get the amazing experience but still have energy left at the end of the day to enjoy the unique restaurants and nightlife that is found mingled amongst the shops.

  • Find gifts made right here in Illinois

    Illinois Made Holiday Gift Guide

    From sparkling wine to Butter Rum popcorn, hand-crafted kitchenware to alpaca wool beanies, the Illinois Made gift guide has unique gift ideas for all.

    Read More
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