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101 things to do in Chicago: shopping

Whether you're looking for upscale stores, trendy boutiques or antique furniture, Chicago's shopping scene has it all

The chain stores on the tourist-choked Mag Mile are fine and all, but if you want a real flavor of Chicago’s shopping scene you need to explore beyond that ritzy strip. Quirky antique stores stocking vintage clothing and decor line Clark Street in Andersonville and Edgewater; the Grand Avenue design district is the place to go for salvaged and new contemporary furniture (usually at eye-popping prices); and Wicker Park​’s “crotch” is the nexus of trendy indie boutiques in Chicago. The best part: Most of these areas are also chock full of bars, restaurants and coffee shops, so you can fuel up between stores.

RECOMMENDED: Take a look at all 101 things to do in Chicago

Chicago's best shopping

Break the bank at Randolph Street Market Festival

Some of the best vintage and antique vendors in the city assemble at this monthly shopping extravaganza. In the summer, the amount of wares to peruse is almost overwhelming—eight acres, both inside the gorgeous Beaux Arts Plumbers Union Hall Building and outdoors in the huge parking lot. In the winter months, the market heads indoors. Prices can be steep, but many vendors like a good haggle.

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Get in the Christmas spirit at Christkindlmarket

For one month spanning November and December, Daley Plaza becomes the happiest place on earth. Nearly 60 Bavarian-style wooden stands are set up to hawk German goods like beer steins and ornaments, and delicious food like potato pancakes, sausages and the holiday market’s signature drink, gluhwein (warm mulled wine). You’ll find Loop workers downing wursts on their lunch break, families visiting Santa, and canoodling couples all getting their fill of holiday cheer.

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Go back in time in the Edgewater/Andersonville vintage district

Clark Street from Carmen to Hollywood Avenues has become a shopping and dining destination over the past several years, but vintage-lovers are especially drawn to the area for its many antique shops. Among the best: Brimfield, which specializes in mid-century furniture and tartan plaid; Scout, a small store with a curated selection of vintage furniture; Room Service, a gorgeous showcase for high-quality, Mad Men–worthy pieces; and Brownstone Antiques, a mess of a store but your best bet for a great deal on a shabby-chic piece. Head northeast to Broadway for the vintage megastores Broadway Antique Market and Edgewater Antique Mall.

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Score a one-of-a-kind contemporary piece in the Grand Avenue design district

Interior design shops and high-end contemporary and vintage furniture dealers line this short stretch of Grand Avenue from Ashland to Western Avenues. Here, you’ll find that very cool (and likely very expensive) piece of furniture that everyone compliments you on when they walk in your home. The crown jewel of this district is Salvage One, which manages to find some of the most unique vintage items we’ve ever seen. It’s also a killer spot for a wedding.

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Pretend you’re in Europe in Lincoln Square

This former German enclave boasts one of the cutest streets in the city, Lincoln Avenue from Leland to Lawrence Avenues. Life moves a little slower on this stretch—literally, as the constant stream of pedestrians crossing this one way street means cars can only crawl. Peruse the produce, Euro chocolates and fantastic international beer selection at Gene’s Sausage Shop; have a glass of wine and pick up the latest best-seller at The Book Cellar; step back in time at Merz Apothecary, in business since 1875; and rest your feet on the shaded Giddings Plaza, featuring a lovely Art Deco fountain.

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Get overwhelmed (and overeat) at Eataly

With 22 restaurants in this Italian megastore—and each one of them packed—you’re going to have some time to peruse Eataly’s vast selection of pasta, olive oil, cheeses, produce, books and more while you wait for your table. Luckily, you can do your browsing while sipping a glass of wine, which always makes shopping more enjoyable, and more prone to impulse purchases.

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Eat and shop till you drop at Maxwell Street Market

This Sunday-only South Loop market is the place to find bargains on such necessities as shoelaces, VHS tapes and cases of off-brand potato chips. But the real reason to go is to eat your way through the many food stands, offering some of the best Mexican food in the city, including huaraches, tacos, birria, elotes, tamales and churros.

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Decorate your walls with prints from Galerie F

If you’re in the market for a screen printed masterpiece that complements your decor, begin your search at Galerie F. From killer concert posters to whimsical prints, you’ll find something frame-worthy at this Logan Square gallery, which stocks pieces from local and national artists. Visitors are always welcome to stop by and admire the work on display, including the shop’s monthly curated exhibitions.

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Shop for toys at Rotofugi

There’s nothing quite like this designer toy store in Lakeview. Grown-ups and kids will love their vinyl figures, capsule toys and limited edition large-format collectibles. Don’t miss the store’s adjoining art gallery, which features monthly exhibits from both rising and established artists.

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Go crate digging for records at Dusty Groove

Record collectors, if you’re looking for deep, deep rare finds, we have to report that the old shops have long ago been picked over by DJs. Still, those needing funky wax must visit this West Town shop specializing in global rhythms, soul, jazz, funk and soundtracks. Bring a tote bag to the posh and comfortable space, as you’re likely to walk out with several pounds of tropicalia, bop and Kinks reissues.

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