The Best Chicago Shopping Streets, Neighborhoods and Malls

The city of Chicago is one of the world’s largest shopping meccas. You’ve probably heard of The Magnificent Mile—the Near North Side stretch of Michigan Avenue that features 460 stores, 275 restaurants, and 60 hotels. Magnificent Mile is home to three multi-level shopping centers, as well, but that’s just one piece of the city’s diverse shopping scene. More department stores can be found on nearby State Street, and the city’s most luxurious outpost are located on the Gold Coast’s Oak Street.

Of course, many neighborhoods feature shopping enclaves beyond mass retailers. Find handcrafted gifts, vintage wares, and contemporary clothing in Andersonville. Shop the hipster-friendly Wicker Park and Bucktown for record shops, consignment boutiques, and independent retailers. Or, scour for loose diamonds on jewelers row and design your own custom creation. Here, the possibilities are endless.

The Magnificent Mile

The Magnificent Mile is synonymous with Chicago shopping. The illustrious stretch north of the Chicago River along Michigan Avenue features three vertical shopping centers surrounded by the world’s best retail outposts. Shop luxury designers like Louis Vuitton, off-price chains like Nordstrom Rack, and children’s favorites like The Disney Store and American Girl Place.

Water Tower Place

Water Tower Place is one of the most prominent malls on the city’s most well-known shopping Avenues: Magnificent Mile. It features anchor stores American Girl Place and Macy’s, as well as the Ritz-Carlton Hotel and a live Broadway theater.

The Shops At North Bridge

The Shops At North Bridge are woven into the fabric of the iconic Magnificent Mile. There is a four-story shopping center as well as street-level stores with designer offerings like Boss, Louis Vuitton, and Alex & Ani. It is also anchored by a four-level Nordstrom, complete with its own cafe.

900 North Michigan

900 North Michigan is The Magnificent Mile’s luxury outpost. The impressive mall is anchored by Bloomingdale’s and full of luxe retailers spanning J. Crew to Gucci. Also, the building houses the Four Seasons Hotel, an Equinox Fitness club, and an array of high-end experiences.

Oak Street Luxury Shops

Oak Street is a high-end enclave in the city’s Gold Coast neighborhood, called the Rodeo Drive of Chicago. Here, you’ll find high-end designers like Georgio Armani, Hermés and Escada as well as luxe jewelry stores including Buccellati and Harry Winston.

State Street Shopping

Anchored by the historic Macy’s, State Street has been an enclave for Chicago shopping since the turn of the century. Today, you can find an array of fast-fashion favorites and trendy boutiques selling everything from apparel to footwear, jewelry, and sporting goods.

River North Gallery District

Art lovers won’t want to miss a visit to the River North Gallery District, home to the world’s largest concentrations of art galleries outside of Manhattan. Here, you’ll find an array of contemporary works and installations to delight and inspire. Not sure where to begin? Take CGN’s tour each Saturday.

Lincoln Square Shops

This North Side neighborhood has German heritage and a small-town feel. Wander the cobblestone streets and stop into the area’s independent boutiques, spanning a retro toy store to an outdoor emporium, with lots of German beer and brats along the way.

Wicker Park/Bucktown Shops

Northwest of the Loop, these trendy hipster neighborhoods host a treasure trove of unique retailers. Find popular outposts like Urban Outfitters and Free People tucked among an array of independent boutiques, vintage stores, and record shops.

Andersonville Shopping Village

Located within the Edgewater neighborhood on Chicago’s north side, Andersonville has a hotbed of locally owned shops along its bustling Clark Street. Take a stroll to enjoy handcrafted gifts, vintage wares, and contemporary clothing while taking in the historic architecture and Swedish culture.

Jewelers Row

In the heart of the Chicago Loop just west of Millennium Park, this stretch of Wabash Avenue features some of the city’s top jewelers. Here, you can shop custom engagement rings, loose diamonds and gems, and beautiful vintage pieces. Or, bring in your pieces to be appraised.

Fashion Outlets of Chicago

Just a half-mile from O’hare airport, Fashion Outlets of Chicago is a shopping mecca of 130 stores. Enjoy off-price bargains from high-end department stores with anchor outlets including Bloomingdale’s Outlet, Saks Off Fifth, Neiman Marcus Last Call, and Nordstrom Rack.