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 designers 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.
A giant designer outlet mall is in suburban Rosemont, next to O'Hare, and one of the largest indoor malls in the country, Woodfield Mall, is a little further northwest in suburban Schaumburg.
For fun and inexpensive shopping for little tchotkes, try looking in the bins at Chinatown.
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)
Every imaginable national clothing store chain is inside this massive, indoor mall – one of the largest in the United States. You'll find everything from Claire's Boutique to Coach, plus kiosks in between the stores inviting customers to sample new products. A dozen restaurants are scattered throughout and entertainment options include Improv, a comedy club, a new 5-D movie theater and a Yu Kids Island, a toddlers play area. For those who want to incorporate exercise with their shopping mix, fitness leaders lead free classes and provide fitness tips on weekly on Thursdays, Fridays and Sundays at the Microsoft store. (847-330-1537)
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.
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). There are excellent boutiques here, too, including the popular Trunk Club, for men's clothes, and Veruca Salt, for women's clothes. (NA)
Need a Jake Arrieta jersey, a Cubs hat, or even Chicago Blackhawks, Bulls and Bears gear? Then head to Wrigleyville, where you'll find the best sports shopping in the city. the best sports shopping is available. Even though these stores are in the shadow of Wrigley Field, where the Chicago Cubs play, they sell gear for all Chicago sports teams and even some non-local teams (just not rivals like the St. Louis Cardinals or Green Bay Packers). On game days, you'll find T-shirt vendors selling less expensive, more creative (and sometimes raunchy) shirts and hats, usually about drinking or about rival teams like the Chicago White Sox. (773-883-2079)
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. People come from all over the world to shop with their children at the American Girl Place store and cafe. (312-440-3166)
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)
Fashion Outlets of Chicago
Fashion Outlets of Chicago is a new mall, with designer shops like Burberry and Prada on the second floor, and less expensive stores like Under Armor, Converse and GAP on the first floor. Because it's next to O'Hare, there are all sorts of traveler-friendly services, like bag checks, free shuttles to and from the airport, and a service deck that tracks your flight. There are lots of specialty, like sports jerseys and hats from Chicago teams, or a Nike store that sells Chicago T-shirts with the Nike logo. But the largely international crowd tends to stay on the designer stores upstairs. (847-928-7500)
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.
Magnificent Mile & Streeterville
Huge stores from huge names - including Apple, Nike, Cole Haan, Uniqlo, Crate & Barrel, Burberry, Neiman Marcus, Old Navy and Tiffany & Co. all have homes on this famous shopping stretch along Michigan Avenue. On the north end of the strip is Water Tower Place and the 900 North Michigan Shops, with stores like 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 shoe department that occupies the entire first floor. There's even a new Chicago Blackhawks store, packed with every imaginable piece of memorabilia from the Stanley Cup champion team.
About Jamie Bartosch
Jamie Bartosch is a lifelong Chicagoan who thinks her hometown is the greatest city in the world. She is an award-winning newspaper reporter, a freelance travel writer, and the mother of two great kids.
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