13 Best Places to Go Shopping in Chicago

Woodfield Mall is an indoor shopping centre with almost 300 unique shops, restaurants, and big-name stores. You’ll find the mall located just off Interstate 290 on Woodfield Mall Drive. Shopping ranges from department stores like JCPenney and Macy’s to small speciality 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 PAC-MAN Entertainment, where you can bowl, play table tennis, or grab a drink at the bar.

Andersonville is a area with a Swedish background that features authentic restaurants and a wide variety of locally owned shops, including furniture and antique stores. You can find Andersonville situated on the North Side of Chicago, and the best shopping is located on Clark Street. There are many unique shops for you to browse through, including Alley Cat Comics, Tilly Vintage Boutique, and Green Sky, which sells eco-friendly handmade crafts. You can 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 streets away from Michigan Avenue. The area is well known for its wide variety of galleries where you can shop for fine art and jewellery. 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 speciality 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 Forever 21 and Old Navy, as well as family-owned shops like AKIRA boutique and Merz Apothecary. 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 the Disney Store along with tasty bites from Latinicity’s street food 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 away from the airport in Rosemount, Illinois. If you're looking for a new outfit for your holiday, you can stop by Gucci, Michael Kors, or Banana Republic, to name a few. Amongst the offerings here, you'll also find a wide selection of art for sale. If you're travelling 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, speciality 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 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 speciality 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 city centre Chicago just off of Michigan Avenue and is well known for luxury shopping, world-class restaurants, and spas nestled within historical buildings. Here, you will find an impressive array of high-fashion and brand-name designers, fine jewellery, and boutique stores, including Giorgio Armani and Buccellati jewellers. 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 T.J. Maxx, Garage, 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 centre on a Sunday, you can browse the stalls at the open-air New Maxwell Street Market. 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 Coach, J.Crew, a 2-level Gucci, and a 6-floor Bloomingdale.

The fancy shopping centre 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.

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 more than 50 world-renowned stores, also featured are 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 20 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 best-known shopping area, “The Magnificent Mile,” which contains endless shopping options amongst more than 450 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. There are also unique stores, such as Dylan’s Sweets Bar and UNIQLO. A massive Nordstrom features 4 stories of shopping opportunities where you can find everything from housewares to children’s toys.

Jewellers' Row is the name of Chicago's diamond district and is a popular area to find fine diamonds and other gemstones and jewellery. You'll find Jewellers' Row located between East Monroe Street and East Washington Street on Wabash Avenue. The shopping options here are endless. The Jeweler’s Centre houses 200 jewellery stores to shop from, or you can visit Donna Jewellery Co, a family-owned store that offers engagement rings and custom-made jewellery. The Classic Gem Fine Jewellery offers custom orders and an extensive selection of loose gems As you stroll down the street, you can admire historic early-20th-century buildings.