Chicago's Best Shopping Is In the Heart of its Neighborhoods

One of the best things about shopping in Chicago is the diversity and support for independent shops within neighborhood communities. Sure, the shopping along the Magnificent Mile and Water Tower Place is pretty sweet but if you want to get a real taste of what Chicago offers, step away from Michigan Avenue and hit up the neighborhoods.

For high-end boutiques like Tod’s and Prada, head towards tony Oak Street, literally steps away from Michigan Avenue. Just a touch west is River North where warehouses have been transformed into art galleries within walking distance of one another.

State Street, also known as That Great Street, is home to Macy’s and several discount chains such a Nordstrom Rack, Old Navy and DSW Shoe Warehouse. Just one block east of the southern end of State Street is Wabash Avenue, home of Jewelers Row.

Independent designers can be found at boutiques that line Division Street in Wicker Park and some outlets within neighboring Bucktown. A host of great indies can be found in family friendly outposts in Andersonville and Roscoe Village as well.

For a little more funky and irreverent, you can’t go wrong in East Lakeview / Boystown.

Whatever your taste or budget, there is a Chicago shopping district that is sure to fit like a glove.

Water Tower Place
There is more to do than just shop at Water Tower Place, an eight-level shopping center located at the northern tip of the Magnificent Mile. In addition to more than 100 stores, there are several restaurants and even a 550-seat theater that is part of the Broadway in Chicago family. Shops like a massive Lego Store, Macy's, Nine West, Banana Republic, Forever 21 and Sephora share space with foodlife, a unique dining venue which features 14 kitchens serving food made from scratch daily. American Girl Caf� on the second level offers children and adults the opportunity to bring their favorite American Girl doll to brunch, lunch, afternoon tea or dinner. (312-440-3166)

Long ago Swedes settled into this North Side neighborhood, leaving the name Andersonville behind to more contemporary residents. Catering to their disposable income and refined tastes, the stretch of Clark Street from Foster Avenue north a dozen blocks features independently owned boutiques, galleries and restaurants. The only chain around? Starbucks. The collection is particularly strong in funky home shops, starting with Brimfield which mixes flea market finds with recovered furniture, plaid woolen blankets and other rustic accessories. Clean, mid-century-modern decor and accessories mixed with primitive pieces and second-hand art distinguish neighbor Scout. Despite gentrification, Andersonville remains a creative neighborhood. Roughly 100 area artists show at the grab-bag market of art, craft and design known as the Andersonville Galleria. The Chamber of Commerce is very active and hosts events throughout the year.

River North
Just a few blocks from Michigan Avenue is Chicago's gallery district in the River North neighborhood. While there are several pockets throughout the city that is home to great art galleries, this has the city's densest concentration and it's also within walking distance to the Merchandise Mart and furniture showrooms. Former warehouses have been turned into exhibition spaces. Several galleries and studios open collectively on a single night about every 6-8 weeks to welcome visitors. Chicago Gallery News, a publication geared toward the art gallery community, hosts free gallery tours every Saturday where attendees visit four galleries (different galleries are chosen for each week). (NA)

Roscoe Village
Next door to Wrigleyville, the refreshingly quiet neighborhood of Roscoe Village has a growing presence of locally owned shops. Spend hours looking through specialty stores along Roscoe Street from children's boutiques and women's apparel and accessories to home décor and furniture. Populated in large by families, the area is very family-friendly so expect to see strollers along the route. The area also boasts several great local coffee shops, restaurants and bars so after a day filled with shopping, hop into vegetarian-friendly Victory's Banner for a meal or Full Moon Tavern for a burger and a beer. If gelato or coffee is more your taste after shopping, stop in Paciugo Gelato & Caffe. (NA)

Magnificent Mile & Streeterville
Apple, Cole Haan, Vince, Ermenegildo Zegna, Giorgio Armani, Salvatore Ferragamo, Burberry, Cartier and Tiffany and Company all have homes on this one mile stretch but nestled within towering skyscraper malls you'll find even more luxury shopping opportunities. Water Tower Place and the 900 North Michigan Shops on one end of the strip count Macy's, Bloomingdale's and Saks Fifth Avenue among their anchors. Just south is Chicago Place which includes Prada among its tenants. On the southern part of the Mag Mile is The Shops at North Bridge which includes a four-story Nordstrom with a first floor shoe department larger than several of neighbor boutiques combined. For a massage or facial, stop by The Peninsula Spa in The Peninsula Hotel just steps away from Michigan Avenue.

East Lakeview/Boystown
Like every neighborhood in Chicago, local stores reflect local tastes. Shops in East Lakeview, also known as gay-friendly Boystown, carry everything from adult novelty gifts to faddish clothes and accessories. This is not the place to find brand names. The true allure of Boystown lies in eclectic, independent boutiques. Locals love digging through the latest stock at consignment stores like Brown Elephant. Others prefer the mix of retro and vintage at Beatnix (which is also drag-friendly). Unabridged Books has a solid collection of gay titles while He Who Eats Mud is the place to go if you need funny, irreverent cards and gifts. (NA)

State Street
Shopping on State Street is Chicago's downtown area is divided in two parts: North and South. North of the Chicago River is a cluster of exclusive boutiques, especially near Rush Street. To the south of the River is where you'll find Macy's as well as discount chains like DSW, Nordstrom Rack, Burlington Coat Factory and T.J. Maxx. Historic buildings and art installations line the famous street but venture one block east of State Street and south of the River and you'll hit Wabash Avenue also known as the Historic Jewelers Row with several old school jewelers happy and willing to show you their displays of diamonds and other gems. (NA)

Lincoln Park
Some of the city's trendiest shops, bars, and theaters call this neighborhood home, as does the famous Steppenwolf Theatre Company. Named for the park that encompasses its eastern border, the neighborhood of Lincoln Park runs from Diversey Parkway to North Avenue. Head towards walk-able Armitage Avenue which much-loved indie shops like Lori's, Vosges Haut Chocolate, Art Effect and Thread Lounge which sit alongside national brands such as BCBGMaxAzria, Intermix, Lush and Nike Training Club. Don't even try to get away with parking in a metered spot and not paying. We're convinced the meters send out a signal to parking patrol attendants as soon as someone parks. If you're lucky to score a parking spot, pay the meter and then shop away!

Oak Street
Oak Street is at the top of Chicago's most prestigious shopping destinations. Prada, Barney's New York, Tod's and Agent Provocateur are just a few high-end shops that adorn the one block shopping district, many of which are located in converted town homes. Oak's collection of shops is wedged between Michigan Ave and North Rush Street and, oddly enough, curiously located on this main street for socialites is Bravco, a long and narrow drugstore that stocks a great selection of hair and beauty products for less than you'd find at a salon. For a see and be seen hot spot, order a glass of champagne at Fred's at Barney's New York. (NA)

Wicker Park & Bucktown
The intersection at North, Damen and Milwaukee Ave form the "fashion triangle" in Wicker Park. Local designers have set up a number of original boutiques, covering clothing and jewelry to worldly home furnishings. Bucktown sits on the hip of Wicker Park. The area is worth distinguishing from its neighbor because of its discount and antique furniture shops. The area is a continuation of urban boutiques and specialty thrift stores. Rule of thumb, if you don't know where else to find it, Bucktown is your best bet. The area is well-known for its arts and dining scene so after you're done shopping, be sure to hit up one of the restaurants.

Megy Karydes has spent more than 20 years as a professional writer and most of her life in Chicago. While she’s traveled extensively internationally, visiting each of the 50 states is on her bucket list. An adventure seeker, she’s game for anything from mixed martial arts training to competing in obstacle course races. A self-proclaimed coffee snob and “greenie” who loves farmer-grown food and locally-grown craft beers & wine. She’s yet to find an outdoor beer garden she doesn’t like.  Mixing writing and food/drink is her specialty, especially when it involves travel. To read her work, visit

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Maps and Directions

Water Tower Place 10Best List Arrow
Type: Malls, Shopping Centers
Neighborhood: Magnificent Mile
Andersonville 10Best List Arrow
Type: Art Galleries, Bookstores, Boutique, Clothing Stores, Contemporary Art Galleries, Farmers Markets, Food / Gourmet Stores, Furniture / Home Decor, Gardening / Nurseries, Gift Stores, Local Picks, Museum Stores, Paper, Arts and Crafts Supplies, Shoes and Accessories, Shopping Districts, Toys and Games, Vintage Clothing Stores, Women's Clothing, Young and Trendy Clothing
River North 10Best List Arrow
Type: Art Galleries, Contemporary Art Galleries, Fine Craft Galleries, Furniture / Home Decor, Sculpture Galleries, Shopping Districts, Specialty Shops
Neighborhood: River North
Roscoe Village 10Best List Arrow
Type: Art Galleries, Boutique, Clothing Stores, Fine Craft Galleries, Furniture / Home Decor, Gift Stores, Jewelry Stores, Local Picks, Men's Clothing, Paper, Arts and Crafts Supplies, Shoes and Accessories, Shopping Districts, Specialty Shops, Women's Clothing, Young and Trendy Clothing
Neighborhood: Roscoe Village
East Lakeview/Boystown 10Best List Arrow
Type: Antique Shops, Bookstores, Boutique, Clothing Stores, Flea Markets, Gift Stores, Local Picks, Men's Clothing, Shoes and Accessories, Shopping Districts, Specialty Shops, Toys and Games, Vintage Clothing Stores, Women's Clothing, Young and Trendy Clothing
Neighborhood: Lake View
State Street 10Best List Arrow
Type: Bookstores, Boutique, Clothing Stores, Department Stores, Fine Craft Galleries, Furniture / Home Decor, Gift Stores, Haute Couture, Jewelry Stores, Local Picks, Men's Clothing, Paper, Arts and Crafts Supplies, Perfume, Cosmetics, Shoes and Accessories, Shopping Districts, Specialty Shops, Women's Clothing, Young and Trendy Clothing
Neighborhood: Downtown
Lincoln Park 10Best List Arrow
Type: Shopping Districts
Neighborhood: Lincoln Park
Oak Street 10Best List Arrow
Type: Boutique, Haute Couture, Men's Clothing, Shoes and Accessories, Shopping Districts, Specialty Shops, Women's Clothing
Neighborhood: Gold Coast
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