Where to shop in Chicago: from mega-malls to small boutiques

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.

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...  Read More


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...  Read More


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...  Read More

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...  Read More

Photo courtesy of Photo by Jamie Bartosch

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...  Read More

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...  Read More

Gold Coast
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...  Read More

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...  Read More

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...  Read More

Magnificent Mile & Streeterville
Photo courtesy of Photo courtesy of Choose Chicago

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...  Read More


Meet 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.