Designer, Vintage, Contemporary and Antique: Chicago's shopping hubs have it all

Chicagoans needn't travel very far to reach designer, artsy, chain or indie shops and tourists from around the world adore coming to the city to shop. Especially since many impressive shopping centers, Water Tower Place900 North Michigan Shops and the Magnificent Mile, are a short stroll or cab ride from downtown hotels. You'll find major national and international brands alongside local, independent favorites. Many malls include entertainment and other amenities, like the Chicago Sports Museum in Water Tower Place or three spas in 900 North Michigan Shops located on the north end of the Magnificent Mile.

Venture just outside the city limits and additional shopping experiences await including the massive indoor mall, Woodfield. If you have access to a car, or need to kill some time while waiting for a flight out of O’Hare International Airport, be sure to visit Fashion Outlets of Chicago in Rosemont. It’s an international shopping mecca with outlet stores like Burberry, Longchamp and Prada, as well as less pricey brands like Nike, PUMA and GAP.

As indoor malls try to reinvent themselves in the Amazon age, neighborhoods like Andersonville and markets such as Randolph St. Market and Vintage Garage Chicago have an independent appeal affording shoppers genuinely unique experiences and goods. Chefs and home cooks adore Green City Market located in Lincoln Park.


900 North Michigan Shops
Photo courtesy of Photo courtesy of Choose Chicago

This shopping center features more than 450,000 square feet of space and includes many well known, upscale stores like a massive Bloomingdale's, MaxMara, Gucci, Micheal Kors, Kate Spade New York, L'Occitane and J. Crew. The complex also includes dining options that range from sophisticated Allium, inside the adjacent Four Seasons Hotel Chicago, Oak Tree (a neighborhood tradition for 38 years) and various casual and grab and go outlets. Out-of-town visitors can stop at the Concierge Desk to receive the Exclusively 900 Card which entitles them to an array of incentives and savings throughout the center. Scan the web site for details on special pop up shops, too.

Recommended for Shopping Malls and Centers because: There is parking outdoors as well as a self park garage attached to the 900 North Michigan Shops.

Jacky's expert tip: Check the web site for special tax-free shopping days and partnerships with Chicago cultural institutions.

Read more about 900 North Michigan Shops →


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 inviting customers to sample new products. Nearly 30 full and quick service eateries are scattered throughout and a new dining pavilion is in the works. Entertainment options include The Improv, a comedy club, and Yu Kids Island, a toddler play area. Mall exercisers can blow out their pedometers walking the more than 2.2 million square feet and if you can take even more retail exposure, hop the trolley to more shops outdoors at Woodfield Village Green and The Streets of Woodfield.

Recommended for Shopping Malls and Centers because: The nearly 300 stores, attractions and restaurants will put you in a shopping stupor.

Jacky's expert tip: Travel during non-rush hour to avoid backed-up exit ramps around the mall.

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As malls lose stores and customers, entrepreneurs find available space and turn it into a shopping experience. Housed in covered parking garage, Chicago's only all-vintage market boasts 75 to 100 vendors filling the space with colorful, retro decor, furniture, clothing, jewelry, art and other fun stuff. In addition, if you have something from grandma's attic, bring it in and experts help figure out what it is and what it's worth. Taking place each month on the third Sunday, the market thrills those searching for vintage lighting, industrial decor, vintage music and vinyl records. Themed shopping events include Midcentury Modern; Vintage Wedding; Record Ramp; Rockabilly and Vintage Clothing; and every year there's the Chicago Vintage Clothing & Jewelry Show and a separate Holiday Market when you can snag classic holiday trees, ornaments, toys, and lighting.

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The urban mall in the core of the Loop draws lots of shoppers from nearby dorms and apartment buildings as well as those who still love State Street shopping. The five-story shopping and entertainment center is home to a two-level Anthropologie, AKIRA Chicago, Zara, Sephora, L 'Occitane en Provence, Disney Store and others. As stores fold, malls are filling square footage with entertainment and in the case of Block Thirty Seven, there's an AMC dine-in movie theater; a climbing and fitness center; and restaurants, including Magnolia Bakery, a grilled cheese joint, Farmer's Fridge for grab 'n' go healthy food, a Kefir shop and Latinicity, an upscale Latin food court and market with 10 innovative kitchens. Block 37 features direct access to Chicago's Pedway, the CTA Red Line and Blue Line.

Recommended for Shopping Malls and Centers because: It's one of the newer malls in downtown Chicago with a decidedly young bent.

Jacky's expert tip: Block Thirty Seven takes its name from the original 58 city blocks established in 1830.

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Lincoln Park

As restaurants proliferate emphasizing the farm-to-table concept and seasonal fare, Chicago's Green City Market has become a lifeline for chefs. The not for profit organization has stocked an extensive selection of conscientiously raised produce and other products for nearly 20 years. Nose around the largest and first year-round sustainable farmers market and nibble cheese, fresh crepes, a slice of Hoosier Mama Pie or Gayle's Best Ever Grilled Cheese. Visit with local farmers and revel in all of the fresh flowers; attend chef demonstrations; and visit the Edible Garden to learn more about gardening through free hands-on workshops. During November and December the market moves indoors assuring comfort as you shop. Not all vendors take credit cards, so carrying cash is smart. Consider the annual Chef BBQ, featuring samples from top restaurants using locally grown produce, responsibly raised meats and craft beverages.

Recommended for Shopping Malls and Centers because: Green City Market the largest and first year-round sustainable farmers market.

Jacky's expert tip: Green City Market outdoor season operates May-October, Wednesday and Saturday from 7am to 1pm. November to April head indoors to Peggy Notebaert Nature Museum.

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Fashion Outlets of Chicago opened in 2013 and quickly became one of the most popular shopping spots near Chicago for tourists and locals. The mall's upper level has high end stores like Burberry, Longchamp and Prada, with the first-floor occupied by favorites like Nike, GAP, PUMA and Saks. There's a free shuttle to the mall from O'Hare International Airport, which is just a few minutes away. The mall's guest services area offers a wide range of travel-related services, including airline baggage check-in and boarding pass issuance. The mall also has several good food options, including health food from Freshii, Vegetarian at Maoz, or confections from Lindt, Häagen-Dazs or Godiva. The facility also offers a multifaceted public art program, THE COLLECTION: Where Art Meets Fashion, site-specific commissions by established and mid-career artists, as well as rotating exhibitions featuring a variety of artists throughout the year.

Recommended for Shopping Malls and Centers because: The large indoor designer outlet mall is close to O'Hare International Airport.

Jacky's expert tip: Parking is free in the indoor lot. Look for green lights above the parking spaces, which indicate an open spot.

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On Chicago's north side, Andersonville is known for its Swedish roots, unique shopping, destination dining and busy urban corridor, Clark Street. Among the shops in the National Historic District are more than a few antique and vintage stores; candy shops; bookstores; lots of spots featuring clothing and accessories; furniture; music; kitchenware; pet supplies; shoes; and food and wine. Visit during the annual Sidewalk Sale that coincides with the annual used book sale. A few of the standouts that you won't find elsewhere in Chicago include the refined presentation at SCOUT;, an array of oddities at Woolly Mammoth Antiques and Oddities; and refurbished large-scale antique cabinets and dining tables at Andersonville Antiques. Cowboys and Astronauts stocks menswear, home comforts and grooming products. Gethsemane Garden Center is known for fresh floral and easy-to-care-for plants and Dearborn Denim creates Made in Chicago jeans that are custom tailored in shop for each and every customer.

Recommended for Shopping Malls and Centers because: Andersonville checks in with over 330 businesses in the Chamber of Commerce membership affording shoppers a unique experience.

Jacky's expert tip: Andersonville is recognized as the "shop local capital of Chicago," with the largest network of local and independent businesses. It is also home to one of Chicago's largest LGBTQ+ populations.

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Named USA Today's "Top 10 American Flea Markets," Randolph Street Market celebrates 15 years in 2018 in Chicago's West Loop neighborhood. Pickers find a one-stop-shop extravaganza with an array of goods plus entertainment, food and fun from more than 300 vendors. The European-style antiques and vintage market (some call it "the Barney's of Vintage") stocks home design, antiques and vintage, fashion, artwork, jewelry and all kinds of treasures. It's strictly indoors during winter but spills out onto the property outside from late spring through fall expanding to over five acres of shopping, continuous live music and refreshments, not to mention people watching. Check the web site for the dates of the monthly two-day market festival that takes place rain or shine.

Recommended for Shopping Malls and Centers because: It's one of the largest, longest running, and highly praised vintage markets in Chicago.

Jacky's expert tip: May-September, a free trolley shuttles shoppers non-stop from Water Tower Place to the market and back.

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Magnificent Mile
Water Tower Place

There's more than shopping at Water Tower Place, an eight-level shopping center located at the northern tip of the Magnificent Mile. In addition to 104 stores, there are myriad dining options, a theater that is part of Broadway in Chicago and the Chicago Sports Museum. Shops like a massive Lego Store, Macy's, Forever 21 and Sephora share space with foodlife, which features 14 kitchens serving food made from scratch daily. People come from all over the world to shop at the American Girl Place store. New shopping include IRL (in real life) an immersive experience that aims to keep brick and mortar shopping alive. You are encouraged to touch, learn and experience new products from brands that are normally only available online. Forever 21's new beauty boutique. Riley Rose, is a bright and colorful new space focused on accessories, cosmetics and home goods for millennials.

Recommended for Shopping Malls and Centers because: In addition to 104 shops, there are full and quick service restaurants plus Foodlife and Foodease with 14 restaurants in a food hall.

Jacky's expert tip: There's a new co-working space with meeting rooms so you can shop, dine and set up work space to use while enjoying the Magnificent Mile.

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"The Magnificent Mile," is perhaps the best known place to shop in Chicago. It's also the most crowded especially in the summer and during holidays. The stores - clothing designers like Chanel, Giorgio Armani, Salvatore Ferragamo, and Burberry, and other stores like Apple, Nike, Sugar Bliss, Uniqlo, Dylan's Candy Bar - are nestled among the skyscrapers. There are malls along the "Mag Mile" as well, including Water Tower Place and the 900 North Michigan Shops, and The Shops at North Bridge, which includes a four-story Nordstrom with a massive shoe department that takes up the whole first floor. The Amazon pop-up and the new Apple Store represent a move forward in tech and in-store tech amenities have advanced for the shopper experience across the board for the past couple of years. Ulta flagship store, Ugg Store and Canada Goose are the latest additions.

Recommended for Shopping Malls and Centers because: Unequalled shopping in Chicago mixed with street performers, historic buildings and great people watching make the Mag Mile one of the country's best shopping districts.

Jacky's expert tip: Start your shopping sojourn early on weekdays for the least crowded experience.

Read more about Magnificent Mile & Streeterville →


Meet Jacky Runice

Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and...  More About Jacky