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Best Chicago Shopping

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In Chicago’s shopping scene, the big chains (Macy’s, the Gap, Pottery Barn and the like) cluster downtown, while the eclectic boutiques and bookstores dot the neighborhoods. If you’re from a town without much in the way of retailers, or you want to get a big chunk of holiday shopping done, by all means hit the Magnificent Mile. But if you want a one-of-a-kind item, you’ll have to head elsewhere. Some tips on shopping in Chicago: Lincoln Park is best for trendy apparel and shoes, while bookworms should make the trek to Hyde Park for both new and used tomes. Looking for vintage records? Wicker Park will set you up. Charming housewares and furnishings abound in Andersonville, near the intersection of Clark Street and Foster Avenue. For hip kids-wear, toys and books, Lincoln Square can’t be beat. Bargain fiends who plan their visits carefully can hit one of Chicago’s big flea markets, which are usually held on weekends in the summer months. We recommend Wolff’s Flea Market in Rosemont, a suburb about 30 minutes’ drive northwest of downtown.

Southport Corridor

Neighborhood: Lakeview
In the Lakeview neighborhood, several cute shops are scattered along Southport Avenue between Belmont Avenue and Clark Street. You’re much likelier to find a one-of-a-kind item here than anywhere downtown. A few not to miss: Candyality, a retro sweet shop that carries Zotz, Necco Wafers, MoonPies and other childhood favorites (3425 N. Southport Ave.). Gourmet food items—and vanilla cupcakes to die for—are the stars of Southport Grocery (3552 N. Southport Ave.). And Uncle Fun, a toy and souvenir shop, is crammed with holographic postcards, tiny harmonicas, bobble heads of every description, and a ton of other weird, entertaining and cheap items (1338 W. Belmont Ave.).

Magnificent Mile

Neighborhood: Downtown
Stretching from the Chicago River to Oak Street, the Magnificent Mile (aka North Michigan Avenue) gathers in one place just about every chain retailer you can think of: Victoria’s Secret, Borders, Crate and Barrel, H&M, Tiffany and dozens more. One of the most popular stores is American Girl (in Water Tower Place, 835 N. Michigan Ave.—just look for the happy little girls carrying red shopping bags). The Mag Mile gets crazy-crowded on weekends and holidays, so if you need a respite from the hordes, head to the Fourth Presbyterian Church (126 E. Chestnut St.) and sit in the courtyard for a quick breather.

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Magnificent Mile  

P.O.S.H.

Neighborhood: Downtown
Vintage restaurant china and glassware, hotel silverware and miscellaneous adorable items make for excellent browsing in this downtown shop. The goods here aren’t the standard dusty antique-shop miscellany, but rather the kinds of things you never knew you wanted till you saw them—like the cereal bowls from a Greek diner, chicken-shaped egg cups or a Belgian hotel desk bell. Owner Karl Sorensen trolls through warehouses, flea markets and auction houses to find these one-of-a-kind gems. And the prices are surprisingly affordable; a vintage mustard pot goes for just $4.

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P.O.S.H.  

The Boring Store

Neighborhood: Wicker Park
Whether you need a pair of glasses with hidden rear-view mirrors, a safe that looks like a soda can or just a fake mustache, you’ll find it here. This small but highly entertaining Wicker Park shop sells spy-themed toys and novelty items. Its name is a tongue-in-cheek attempt at keeping the store itself undercover—hence its self-description as “The Least Intriguing Retail Outlet in the Midwest.” The shop is the retail arm of 826CHI, an educational center that offers free writing classes and tutoring to kids, and all of the proceeds support those efforts. In our opinion, there’s no better excuse to splurge on a banana-shaped cell-phone cover.

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The Boring Store  

State Street

Neighborhood: Downtown
State Street (specifically, the portion of it between Randolph and Jackson streets) represents the bargain alternative to the Magnificent Mile. Several discount stores are clustered here—including Loehmann’s, Filene’s Basement, T.J. Maxx and Nordstrom Rack—making it retail heaven for people who enjoy pawing through a pile of marked-down cardigans. For a taste of Chicago history, wander through Macy’s at 111 N. State St.; it was once the flagship location of iconic department store Marshall Field’s, and many Chicagoans are still bitter about the 2006 buyout. The food court in the basement is a nice place to catch your breath.
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