13 Best Places to Go Shopping in Chicago

Woodfield Mall is an indoor shopping center with almost 300 unique shops, restaurants, and big-name stores. You’ll find the mall located just off Interstate 290 on Woodfield Road. Shopping ranges from department stores like JCPenney and Macy’s to small specialty stores such as Mia’s Wish and Native Arts.

You can choose from restaurants offering fast food, falafels, Chinese, pizza, Mexican, and much more. If you’re looking for something different, the Improv Comedy Club presents comedy acts to enjoy while you eat. For even more fun, you can check out Enterrium, where you can bowl, play arcade games, or grab a drink at the bar.

Andersonville is a neighborhood with a Swedish background that features authentic restaurants and a wide variety of locally owned shops, including furniture and antique stores. Andersonville is situated on the North Side of Chicago, and you can find the best shopping opportunities on Clark Street.

There are many unique shops for you to browse through, such as the Alley Cat Comics. You can also find several fantastic Swedish eateries, as well as restaurants serving Irish, Middle Eastern, and Japanese cuisines.

River North features luxury shopping, trendy restaurants, popular landmarks, and numerous entertainment options and can be found a few blocks away from Michigan Avenue. The neighborhood is well known for its wide variety of galleries where you can shop for fine art and jewelry. You can also find high-end furniture and decor and designer clothing boutiques.

You'll have a wide array of restaurants to choose from, but the area is best known for its upscale steakhouses and fusion restaurants. While you’re in River North, you may also enjoy attractions such as Navy Pier or the Museum of Contemporary Art.

State Street offers a little bit of everything, from malls and department stores to bargain shops and specialty stores, with the best shopping located between Jackson Boulevard and Lake Street. As you walk down State Street, you can shop at a wide variety of popular stores, such as Urban Outfitters and Foot Locker, as well as local boutiques.

You can shop familiar brands at Macy's while enjoying the architectural beauty of its massive granite columns, historic Burnham Fountain, and sparkling Tiffany ceiling. State Street's Block 37 features shops like Anthropologie and Zara along with tasty bites from Which Wich superior sandwiches and Magnolia Bakery’s cupcakes.

The Fashion Outlets of Chicago complex features more than 130 stores with heavily discounted goods and is located about 5 miles (8 km) away from the airport in Rosemount, Illinois. If you're looking for a new outfit for your vacation, you can stop by Gucci, Michael Kors, or Banana Republic, to name a few.

Among the offerings here, you'll also find a wide selection of art for sale. If you're traveling to or from the airport, the outlet offers services such as boarding pass printing and luggage storage for added convenience.

Water Tower Place features 8 levels of shopping and includes popular stores, spas, boutiques, specialty shops, and restaurants, and it's found along the iconic Magnificent Mile, north of Pearson Street. Whether you’re looking for men’s and women’s fashion, electronics, health and beauty, or fitness gear, you're sure to find it here.

When you're ready for a lunch or dinner break, there are several fast-food restaurants, or you can duck into Harry Caray’s 7th Inning Stretch Restaurant and Sports Bar to watch a game while you enjoy a bite to eat at the bar.

Lincoln Square, on the north side of Chicago, features a variety of specialty stores for all ages and is a great spot to enjoy a nice stroll as you shop. If you're looking for gifts to bring home, make a stop at Merz Apothecary to pick up natural lotions, candles, and more, or try Laurie’s Planet of Sound for Indie records.

Children will love Timeless Toys with its educational toys, books, and puppets or Quake Collectibles, featuring vintage and modern toys. With all the unique offerings, you're sure to find something for yourself or for a perfect gift.

Oak Street is situated in downtown Chicago just off of Michigan Avenue and is well known for luxury shopping, world-class restaurants, and spas nestled within historical buildings. Here, you’ll find an impressive array of high-fashion and brand-name designers, fine jewelry, and boutique stores, including Giorgio Armani and Buccellati jewelers. 

When you’ve shopped to your heart’s content, you can treat yourself to a gourmet meal at one of the area’s many fine-dining restaurants or grab a drink at a swanky bar and lounge.

The Maxwell lies a few blocks west of South Loop and the Chicago River. The ground-level mall features a variety of casual restaurants and retailers, including Burlington and Nordstrom Rack. Since it’s a relatively small mall, you can enjoy a relaxed shopping experience as you won’t need to fight large shopping crowds.

If you visit the shopping mall on a Sunday, you can also check out the open-air Maxwell Street Market on Maxwell Street, just a few minute’s drive from the mall. Here you’ll find artisan food, fresh produce, and sometimes live music.

900 North Michigan Shops takes luxury shopping and entertainment to new heights, starting with its stunning architecture. You’ll find a chef-driven food court, indoor golf simulator, and more than 70 high-end retailers here. Shops include J.Crew, a 2-level Gucci, and a 6-floor Bloomingdale.

The fancy shopping mall is situated within a lofty skyscraper on the north end of Chicago’s Magnificent Mile. You could combine a shopping spree with a visit to the iconic 875 North Michigan (formerly the John Hancock Building), with its 360-degree Observation Deck.

The Shops at North Bridge is a stylish spot in Chicago offering an answer to your retail therapy needs. Spanning 6 blocks along Chicago’s Magnificent Mile, you’ll find all of the major retail stores next door to each other. From a flagship Nordstrom to 50 world-renowned stores, The Shops at North Bridge features an impressive lineup including APM Monaco, Untuckit, MCM Worldwide, and White House Black Market.

When you need to take a break, you can refuel at one of the mall’s several eateries. With so much to see and buy, you could easily spend a couple of hours or more here.

Streeterville is home to Chicago’s most well-known shopping area, "The Magnificent Mile," which contains endless shopping options and is home to hundreds of stores. Magnificent Mile spans 13 blocks, from Oak Street to the Chicago River.

If you’re searching for fashion items, you’ll find clothing stores such as Burberry and Chanel as well as footwear from the Ugg Store and Nike. A massive Nordstrom features 4 stories of shopping opportunities where you can find everything from housewares to children’s toys.

Jewelers' Row is the name of Chicago's diamond district and is a popular neighborhood to find fine diamonds and other gemstones and jewelry. Jewelers' Row is located between East Monroe Street and East Washington Street on Wabash Avenue. 

The shopping options here are endless. The Jeweler’s Center houses 180 jewelry stores to shop from, or you can visit Donna Jewelry Co, a family-owned store that offers engagement rings and custom-made jewelry. As you stroll down the street, you can admire historic early-20th-century buildings.