Best Shopping in Chicago

Shopping in Chicago: sweet spots abound all around town

Chicago has department stores a la Macy's, Nordstrom and Bloomingdales offering sprawling floors of inventory as well as plenty of independently owned shops stocking the uncommon while sporting a ton of heart and personality. 

Visitors and locals adore shopping along the Magnificent Mile and Water Tower Place (as evidenced by the throngs no matter the weather) because, honestly, it's all there from Uniqlo to Tiffany, American Girl Place in Water Tower Place to 50 stores and 20 restaurants in The Shops at North Bridge. You can stroll and window shop outdoors and pop into one of the indoor malls like 900 N. Michigan Shops for a breather from icy winds or thick-as-pea-soup humidity in the summer. Attracting tons of international tourists, Michigan Avenue is perfect for people watching, too. Those shopping according to Gywneth's Goop, may want to take a turn just a tad west for Oak Street's couture and class.

Like many urban downtown areas, State Street had its tacky era but the Great Street is back teeming with college students and their fave shops like American Apparel and Urban Outfitters. Macy's, ensconced in our beloved Marshall Field's building, is a testament to the rich history of American department stores.

Chicagoans love their neighborhoods and the indie retailers lining Wicker Park, Bucktown, Andersonville, Lincoln Square, Lakeview and others. Take a water taxi to Chinatown for great eats and shops offering inexpensive imported treasures. 

The suburbs beckon with an impressive designer outlet mall with permanent and rotating art exhibits in suburban Rosemont, next to O'Hare, and one of the largest indoor malls in the country, Woodfield Mall, lies just a little further northwest in suburban Schaumburg.


Lincoln Park

Some of the city's most impressive boutiques and attractions call this neighborhood home - does Steppenwolf Theatre Company ring a bell? Named for the park that encompasses its eastern border, Lincoln Park runs from Diversey Parkway to North Avenue and it's filled with delightful discoveries among the Victorian row houses. Art Effects looks as though it's all about home decor but check out the back room for women's clothes, accessories, and jewelry. The flagship Tie Bar offers new apparel and accessory releases monthly which will put you together from tie to toe. Head to Laudi Vidni (the name of the shop is "individual" spelled backward) for custom leather bags and accessories individually handcrafted. Lori's Shoes is known for Italian exclusives and affordable prices. Guys should check off stops at the Black Tux, Bonobos, Indochino and Mugsy Jeans. And everyone will want to work in an appointment at Kohler Waters Spa - no need to trek to Wisconsin, just Lincoln Park.

Recommended for Best Shopping because: The neighborhood is more than an historic park and zoo. Lincoln Park is packed with world-class shopping, interesting dining and one-of-a-kind entertainment options.

Jacky's expert tip: Take a break for a festive beverage, lunch or dinner at the new Kala, a Mediterranean dining experience.

Read more about Lincoln Park →


During the 19th-century immigrant Swedish farmers began to move north from the center of the city into what was then considered a suburb of Chicago. By the 20th century, the entire commercial strip was dominated by Swedish businesses and today the smorgasbord includes the Swedish American Museum and one-of-a-kind, locally owned, independent businesses. Among the shops in the National Historic District, you'll find 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. The community celebrates neighborhood-wide seasonal fests and spectacular sidewalk sales in summer. The Andersonville Galleria features over 90 tenants stocking apparel, jewelry, artwork, home goods, antiques fair trade and gourmet items. Unfortunately, Swedish Bakery recently closed after 88 years but you can still get Swedish meatballs, pickled herring or the Stockholm Special at Svea.

Recommended for Best Shopping because: It's refreshing to shop among so many indie businesses in a culturally rich neighborhood.

Jacky's expert tip: Andersonville restaurants are notable especially in the dessert department with standouts like Lost Larsen, Taste of Heaven, First Slice Pie Cafe and Defloured, a gluten-free bakery.

Read more about Andersonville →

Fashion Outlets of Chicago offers more than 130 designer outlets, high-end amenities and a contemporary art collection. The art program, THE COLLECTION: Where Art Meets Fashion, has a rotating exhibition and 19 site-specific permanent commissions by established artists. The Rosemont mall is anchored by Bloomingdale's The Outlet Store, Forever 21, Nordstrom Rack and Saks Fifth Avenue OFF 5TH. You'll find world-renowned brands like Gucci, Prada, Tory Burch, Michael Kors, Burberry, as well as national brands like Banana Republic, J.Crew Factory, Swarovski, Nike, Under Armour and Cole Haan. Those with little consumers appreciate Fashion Outlets' children's wing with Disney Outlet, Carter's, Oshkosh B'gosh and Gymboree Outlet, all situated on level one. Because it's five minutes from O'Hare, expect a bevy of traveler-friendly services, like taxi service, luggage check and boarding pass printing.

Recommended for Best Shopping because: It's infinitely better than hanging around O'Hare if you have a long layover or flight delay.

Jacky's expert tip: Free parking in an indoor seven-level "smart" garage utilizes red or green lights above each space indicating availability for drivers to easily find a parking space.

Read more about Fashion Outlets of Chicago →


Chicago's gallery district in the River North neighborhood is just a few blocks from Michigan Avenue and if you're shopping for original art, this is your bliss among the former warehouses turned exhibition spaces. If the creme de la creme of furniture and home decor is calling, you're a few blocks from the Merchandise Mart's furniture showrooms. The first week of December, it's the One of a Kind Show and Sale at The Mart when hundreds of artists and and designers offer truly unique goods. River North is home to home design showrooms, bespoke suit and tux shops as well as Glamour Closet where brides-to-be can choose among designer wedding gowns at up to 75% off retail. Treat yourself at the chocolate shop/café, L.A. Burdick, and P.O.S.H. has been enchanting locals and visitors for years with its flea market finds, hotel silver and French kitchen accessories.

Recommended for Best Shopping because: River North is awash in art galleries, fine furnishings, new bars and restaurants.

Jacky's expert tip: The Merchandise Mart is not only a landmark building, but it's also a great place to shop for higher-end furniture in its many showrooms.

Read more about River North →


Like many urban downtown areas, State Street had it's sad, downtrodden days but the Great Street is back teeming street musicians, college students and their favorite shops like American Apparel, Puma, Sephora, Forever 21 and Urban Outfitters. Macy's, ensconced in our beloved Marshall Field's building and the second largest department store in the world, is a testament to the rich history of American department stores, and don't miss Block 37 with its eclectic mix of retail and dining in a five-story shopping mall. Notable shops in Block 37 include Anthropologie, L'Occitane en Provence, Sephora and fun spots to nosh like Gayle V's Best Ever Grilled Cheese. The food court at Seven on State in Macy's offers Chicago favorites, tacos and even the famous chicken pot pie from the Walnut Room. Basketball fans should head for the House of Hoops by FootLocker.

Recommended for Best Shopping because: It was the center of the Chicago shopping universe for generations of Chicagoans.

Jacky's expert tip: Lunch at the Walnut Room, the first restaurant ever opened in a department store (1905), on the seventh floor of Macy's.

Read more about State Street →

Lakeview encompasses West Lakeview, the Southport Corridor, Wrigleyville and Northalsted. Then there's adjacent Roscoe Village (nicknamed "The Village Within the City" for it charming small town feel). It adds up to a plethora of actually fun shopping. Lakeview is home to the Cubs, so fans and tourists have their choice of souvenir shops. Expect clothing and accessory boutiques, art galleries, antique shops plus the Brown Elephant is a must for resale furniture, clothing and books. The Southport Corridor boasts wonderful clothing and accessory boutiques. Belmont and Lincoln Avenues, Clark, Halsted and Broadway Streets feature retro finds, gourmet groceries, and biker gear combined with great joe at Heritage Bicycles. Get that new or vintage ax at The Chicago Music Exchange. Roscoe Village is a joy to shop for vintage finds, accessories, shoes, apparel and kids' stuff. When it's time to refuel, the Mediterranean French cuisine at Le Sud never disappoints.

Recommended for Best Shopping because: Serious shoppers who eschew run-of-the-mill chain stores will be pleased with the eclectic finds in Lakeview/Roscoe Village.

Jacky's expert tip: Visit the Roscoe Village Farmers Market Sundays from June to October or pencil in a visit during the annual Roscoe Village Burger Fest.

Read more about Lakeview/Roscoe Village →

European ambiance, cobblestone streets and quaint storefronts make Lincoln Square (and the Ravenswood corridor) an appealing outing for shopping, dining, drinking and discovery. Home to the Old Town School of Folk Music where you can catch a concert in an intimate space and then purchase a mandolin, Lincoln Square feels like the Chicago immigrants built in the 19th/20th centuries. Stop in Gene's Sausage Shop and Delicatessen, a full range European market. See what local artists and artisans are creating at a bevy of boutiques and galleries and don't miss Merz Apothecary, Chicago's oldest pharmacy, established in 1875. Gear Head Outfitters is a huge outfitter for outdoor apparel and travel gear. There are shops specializing in books, clothing, jewelry, home decor and vintage goods. And don't get us started on the restaurants. Newer additions include Alma Curiosa; Raw Edge; and Bon Femmes for art and home decor made and designed by women.

Recommended for Best Shopping because: Lincoln Square/Ravenswood may be the best example of Chicago's small business community.

Jacky's expert tip: Take the time to sense the rich history of Lincoln Square through its murals and other public art.

Read more about Lincoln Square/Ravenswood →

Gold Coast

If words like Prada, Hermes, Christian Louboutin, Chanel, Graff, Richard Mille and Escada increase your pulse rate, Oak Street should be your shopping destination in Chicago. High-end shops, from international couture houses to local boutiques, adorn the one block shopping district, many of which are located in converted townhomes. Oak Street"s collection of shops and eateries are wedged between Michigan Ave and North Rush Street. There are plenty of stylish spots to nosh and get plied with bubbly after a foray to the in-house Vera Wang bridal salon at Bella Bianca (on Rush St.) Then visit Harry Winston, Graff or Buccellati to pick out the rings.

Recommended for Best Shopping because: It's only one block and infinitely more civilized (and spendy) than the mall.

Jacky's expert tip: Treat yourself to inspired Japanese/Latin fusion at Mansion on Rush that also offers a perch for people watching.

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Once the purview of Nelson Algren, Wicker Park and Bucktown have been disparaged as "hipster central" but take it from someone who grew up in the hoods pre-gentrification - this is cool, too - and safer. Browse Japanese and Danish design at Moth; on-trend clothing, apothecary home decor and gifts at Una Mae's; great vinyl at Reckless Records or Shuga Records; and p.45 for a curated collection of emerging and nationally recognized designers. Enaz, unique to the Chicago area, has a new location here offering denim, sweaters, t-shirts, dresses and accessories. Asrai Garden, since 1999, stocks fine jewelry and "magical curiosities." The area is a magnet for artists who work on canvas and the plate so don't leave without having a bite and a pint. Better yet, plan to visit during one of the annual events like the WPB Summer Sidewalk Sale and Wicker Park Fest.

Recommended for Best Shopping because: Bucktown and Wicker Park are magnets for artists, musicians, modern indie shops and chefs.

Jacky's expert tip: Duck into Piece Brewery and Pizzeria, one of the friendliest eateries in these parts.

Read more about Wicker Park & Bucktown →

Apple, Nike, Cole Haan, Uniqlo, Burberry, Neiman Marcus, and Tiffany & Co. all call the famous shopping stretch home. On the north end of the strip is Water Tower Place and the 900 North Michigan Shops, with stores like Gucci, Max Mara, J. Crew, Sur La Table and Bloomingdale's among the anchors. You'll find The Shops at North Bridge on the southern section which includes a four-story Nordstrom with a shoe department that occupies the entire first floor. Hello, Manolo! Among the 450 retailers on the Mag Mile are sports stores; boutiques for pets and children; Fine Art galleries; designer and luxury shops; jewelry shops; gourmet food stores; home goods and florists; cosmetics' hubs; all kinds of dining; and the ginormous Starbucks Roastery to help fuel you through this daunting shopping experience. And the Museum of Ice Cream just opened in Tribune Tower.

Recommended for Best Shopping because: Unequaled 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