[2023 GUIDE] The Best 16 Places for Shopping in Chicago | TrotterHop

Shopping in Chicago is some of the best things to do in the city, truly a great destination for a shopping spree. With a huge variety of retail options, ranging from discount outlet malls to high-end fashion, there is something for everyone. Stroll through charming areas and browse specialty boutiques or take in the view of the city while shopping in a skyscraper. There are also many malls and plazas to choose from.

Chicago is the largest and most vibrant city in the United States. It offers a home away from home feeling to all who visit. From towering skyscrapers and brightly lit streets to world-class museums, Michelin-star restaurants, and entertaining theater performances, the city is sure to impress.

Shopping enthusiasts will be thrilled by each street’s numerous boutiques and designer labels. Chicago is the perfect place to explore and enjoy a luxury and affordable shopping experience.

The Best 16 Places for Shopping in Chicago

1. Magnificent Mile (Michigan Ave.)

The Magnificent Mile is one of the most iconic shopping areas in the world. Located between the Michigan Avenue Bridge and Oak Street, this cosmopolitan strip on downtown Michigan Avenue is packed with history. There are department stores, multistory retail centers, luxury boutiques, and brand-name retail chains, all within a scenic stroll of each other.

One of grand boulevard’s three multistory malls is 900 North Michigan Shops. There are 70 stores spread across seven levels, offering national brands and unique boutiques.

Water Tower Place is another historic mall located on the Magnificent Mile. It has an eight-level atrium with stores like Coach, Finish Line, American Girl Place, and the LEGO Store.

The Shops at North Bridge is another shopping and dining destination on the Magnificent Mile. It spans six blocks and features 50 world-class specialty shops, 20 restaurants, and three hotels. There are a variety of retailers here, from Louis Vuitton to Nordstrom.

2. State Street

Chicago’s State Street is a one-stop spot for the city’s best shopping. Locals and visitors flock here for the blocks on blocks of modern malls, historic department stores, specialty shops, bargain options, and more – all located in the central area just a few blocks from Millennium Park, the Riverwalk, Theatre District, and more classic Chicago sights. Here’s where to go during your shopping spree on Chicago’s State Street.

Macy’s on State Street is a National Historic Landmark, boasting a grand exterior of towering granite columns and the massive Great Clocks that greet shoppers. Inside is equally impressive with a shimmering Tiffany ceiling that soars above the first-floor cosmetics department and the historic Walnut Room, the first restaurant in a department store, with Austrian chandeliers, century-old wood paneling, and Mrs. Hering’s Chicken Pot Pie, a staple on the menu since 1907.

For a true State Street shopping experience, stick to the stretch of State between Lake Street to Jackson Boulevard. Here you’ll find trendy shops, mega-retailers, local boutiques, and more. Block 37, just across the street from Macy’s, is a hip shopping hub filled with cool stores and eateries.

Nearby, Merz Apothecary is tucked away inside the Palmer House Hilton Hotel, offering hard-to-find perfumes and colognes, old-school shaving products, and specialty toiletries. Around the corner, AKIRA, the Chicago boutique, is a stylish Midwest staple stocked with statement-making women’s clothing. You can also find all your favorite trend-setting stores, like UNIQLO, TJ Maxx, Nordstrom Rack, Express, Old Navy, Target, Journeys, and Zumiez.

3. South Loop

If you’re looking to spice up your wardrobe, South Loop is the perfect place. This vibrant Chicago neighborhood is home to the Roosevelt Collection Shops, an open-air shopping center with various clothing stores. Banana Republic, Nordstrom Rack, H&M, Old Navy, LOFT, Francesca’s, and Victoria’s Secret are just some of the brands featured in the mall. You’ll also find a movie theatre, restaurants, and other retailers in the complex.

In addition to the shopping center, the South Loop offers a selection of boutiques off the beaten path. A’nies Accents is an upscale spot for female fashion in the area, and you can make private appointments with an in-store stylist. Flaunt is another cozy boutique with clothing and accessories for all your fashion needs. The store frequently holds purse swaps and trunk shows.

You can explore the stores throughout the Loop for more shopping options. These stores are easily accessible by foot, public transit, or shared rides from South Loop.

4. West Loop

West Loop, Chicago, remains one of the Windy City’s most popular neighborhoods, offering an array of trendy dining, living, and retail options. If you’re seeking retail therapy, you’ll find some of the best shopping opportunities in West Loop. 

Randolph Street is widely known as ‘Restaurant Row’, but it also provides shoppers with a selection of stores. You’ll discover national retailers like Anthropologie and Free People and local boutiques like the Fig Tree. 

In the past year, the neighborhood has welcomed several new stores. Reality Star, Kristin Cavallari, opened a second Uncommon James Store in West Loop, offering jewelry and home goods. Madewell also made its debut, offering women’s apparel. Men can find stylish attire at Independence, a menswear boutique with over 50 American-made brands. 

These shopping options make West Loop one of the Windy City’s hottest neighborhoods.

5. Hyde Park

Hyde Park is a renowned cultural center in the city. It was President Obama’s past home and is known for the esteemed University of Chicago, with many Nobel Prize winners from the neighborhood.

You can find some of the city’s best boutiques within the area. 57th Street Books offers a fascinating selection of books with a labyrinth of rooms to explore, helpful staff, and rare finds. Toys et Cetera stocks creative, constructive, and enjoyable toys. Dearborn Denim offers comfortable jeans made and cut in Chicago.

The Silver Room is also a great place to check out. With a mission to form a global community through art and culture, it provides a variety of apparel, apothecary, accessories, books, and gifts.

6. River North

Located in Chicago’s River North neighborhood, the gallery district is just a few blocks from Michigan Avenue. This district is a paradise for anyone buying original art, filled with former warehouses converted into exhibition spaces. Additionally, those looking for furniture and home decor can visit the Merchandise Mart to find the creme de la creme of furniture showrooms.

The first week of December is an especially exciting time to visit the River North neighborhood, as the One of a Kind Show and Sale is held at The Mart. This event features hundreds of artists and designers who offer truly unique goods. In addition, River North is home to home design showrooms, bespoke suits, tux shops, and Glamour Closet, where brides-to-be can purchase designer wedding gowns at up to 75% off retail.

Finally, visitors to the area can indulge in a luxurious treat at the chocolate shop and café, L.A. Burdick, or take a look around P.O.S.H., which has been enchanting locals and visitors for years with its flea market finds, hotel silver, and French kitchen accessories.

7. Oak Street (Gold Coast)

Oak Street in Chicago is a one-block shopping district with high-end stores and eateries. Many stores are in converted townhomes, making it a unique shopping experience. Located between Michigan Ave and North Rush Street, Oak Street is the place for luxury shopping. From Prada to Christian Louboutin to Hermes, there is something for everyone. 

After a shopping spree, there are plenty of stylish spots to nosh and get plied with bubbly. For brides-to-be, there is the in-house Vera Wang bridal salon at Bella Bianca (on Rush St.) Or, if you are looking for rings, check out Harry Winston, Graff or Buccellati. 

Oak Street is the perfect destination for luxury shopping in Chicago.

8. Old Town

Old Town has been a popular retail and manufacturing destination in Chicago for decades. Companies like Crate & Barrel and Dr. Scholl’s opened their first stores in this neighborhood. 

Visitors to Old Town today have many different stores to choose from. These stores have been part of the neighborhood for over 15 years, providing the local community with a wide range of products and services.

9. Lincoln Park

Armitage Avenue and Halsted Street are home to some of the city’s most popular shops. You can find designer shoes, one-of-a-kind art, and gifts. Art Effect is a great place to find Pinterest-worthy home decor. This welcoming shop offers a fun and affordable selection, with a back room full of women’s clothes, accessories, and jewelry.

All She Wrote is another great shop in the area. This stationery shop has thoughtful gifts and cards for every occasion. Lastly, Laudi Vidni is a must-visit for custom leather bags and accessories. They are handcrafted and shipped within a few weeks.

10. Southport

The Southport Corridor is ideal for those who prefer shopping in independent stores. Easily accessible via the CTA Brown Line, Southport is a short walk from Wrigley Field. The area represents what Chicago is all about, with an eclectic mix of clothing and accessory boutiques, delicious restaurants, and family activities.

Krista K is a popular local boutique that stocks a selection of both emerging designers and classic favorites. For stylish men’s apparel, visit the Denim Lounge for Men. For stylish bags and gifts, M2 Boutique is the place to go. Additionally, Uncle Dan’s is a long-standing outdoor and equipment store that offers clothing and accessories for men, women, and kids.

When it’s time for a break, head to Frio Gelato to enjoy a scoop of fresh gelato or sorbet. Southport Corridor also features several upscale national stores such as Anthropologie, Kendra Scott, Lush Cosmetics, Bonobos, Evereve, Lou & Grey, and Johnny Was. Plus, there’s an Amazon Store located in the area.

11. Lakeview & Roscoe Village

Lakeview is a unique area that is made up of many smaller communities. Each of these communities has its own shopping districts and local businesses. We recommend visiting Broadway in Lakeview East, Belmont and Broadway in Northalsted, and Southport Corridor near Wrigleyville. 

There are some great boutiques that you should visit while in Lakeview. Heritage Bicycle General Store is a great local coffee shop that sells custom handmade bicycles made in Chicago. Waxman Candles is a family business that continues to make handmade candles and ceramics. Inkling is a shop filled with interesting curiosities, including quirky gifts, greeting cards, housewares, and jewelry by talented artists.

12. Andersonville

Andersonville is known as the “shop local Capital of Chicago,” making it an ideal place to explore the city’s local boutiques. The neighborhood has a unique personality, born from its history as the heart of Chicago’s Swedish immigrant community. Visitors can find various stores, from the Andersonville Galleria, with over 100 vendors, to the Clark Street shops, which offer unique clothing, accessories, housewares, and books.

Women and Children First have been an Andersonville institution since 1979. It is one of the largest feminist bookstores in the country, offering a selection of books and events that celebrate women and LGBTQ+ authors. Milk Handmade is another Andersonville favorite, featuring handmade clothing, accessories, apothecary, and home goods created by local independent designers.

13. Wicker Park/Bucktown

If you’re into all things fun and funky, Wicker Park and Bucktown is the place for you. This trendy area is known for its hipster culture, thriving arts community, and indie shopping. You’ll find boutiques and vintage stores throughout the bustling “six corners” intersection of Milwaukee, Damen, and North Avenues. 

For example, Transit Tees features apparel and accessories from local artists and artisans. At the same time, Shuga Records is a music label and a record store with friendly staff to guide you through its massive selection of vinyl. There’s also Asrai Garden, which sells luxurious fine jewelry and unusual curiosities, Vintage Underground, full of gently used clothing and costume jewelry, and Penelope’s and Gemini for carefully curated collections of hip men’s and women’s clothing. Lastly, Una Mae’s is the perfect place to find unique contemporary clothing labels, lifestyle products, and gifts.

14. Lincoln Square

Lincoln Square and the Ravenswood corridor offer a unique experience for visitors. Streets are lined with cobblestone and quaint storefronts that add to the cozy European ambiance. This area is the perfect destination for shopping, dining, drinking, and discovering.

The Old Town School of Folk Music is one of the most popular attractions. This intimate space hosts concerts and also sell mandolins. Gene’s Sausage Shop and Delicatessen is also a popular destination, as it is a full-range European market. Visitors can also explore a variety of boutiques and galleries showcasing unique artwork from local artists and artisans. Merz Apothecary, established in 1875, is the oldest pharmacy in Chicago and is worth a visit. Gear Head Outfitters is a great place to find outdoor apparel and travel gear. Additionally, plenty of shops specialize in books, clothing, jewelry, home decor, and vintage goods.

For dining, Lincoln Square and the Ravenswood corridor certainly don’t disappoint. Recent additions include Alma Curiosa, Raw Edge, and Bon Femmes, which feature art and home decor made and designed by women.

15. Pilsen

Pilsen is a vibrant and funky neighborhood in Chicago known for its Mexican heritage. It offers plenty of cool bars, family-owned taquerias, and unique shopping experiences. If you’re looking for unique treasures, 18th Street is the place to be. You’ll find many vintage shops, such as Pilsen Vintage and Knee Deep Vintage.

You can also find secondhand novels at employee-owned Pilsen Community Books, sustainable goods at eco-boutique The Shudio, and vinyl at 606 Records. To bring home a piece of Mexican artistry, visit Mestiza, a colorful boutique founded by two artists in 2004. You can also find artistic objects at the gift shop for the National Museum of Mexican Art.

16. Rosemont (Fashion Outlet of Chicago)

Fashion Outlets of Chicago is more than just a shopping destination. The outlet mall offers a collection of 130 designer outlets, high-end amenities, and a rotating art exhibition. THE COLLECTION: Where Art Meets Fashion showcases 19 permanent commissions by established artists. The mall is anchored by Bloomingdale’s The Outlet Store, Forever 21, Nordstrom Rack, and Saks Fifth Avenue, OFF 5TH. World-renowned brands like Gucci, Prada, Tory Burch, and Michael Kors, and national brands like Banana Republic, J.Crew Factory, Swarovski, Nike, Under Armour, and Cole Haan, can be found here.

The mall also caters to families with its children’s wing on level one, featuring Disney Outlet, Carter’s, Oshkosh B’gosh, and Gymboree Outlet. For travelers’ convenience, Fashion Outlets of Chicago offers taxi service, luggage check, and boarding pass printing, all just five minutes away from O’Hare.

Shopping in Chicago FAQ

What is the famous shopping street in Chicago?

The Magnificent Mile is one of the world’s most famous shopping streets in Chicago. There are many opportunities to eat and shop around this iconic street.

Is Chicago known for shopping?

Yes, Chicago is renowned for its shopping opportunities. It offers various options, from discount outlet malls to high-end fashion and luxury art and jewelers.

What is the most popular shopping area in Chicago?

The most popular shopping area in Chicago is the Magnificent Mile and Streeterville. Water Tower Place and the 900 North Michigan Shops are located at the north end of the strip and boast stores such as Gucci, Max Mara, and others.

What famous stores are in Chicago?

Chicago is home to famous stores, such as The Shops at North Bridge, Patek Philippe, Rolex Boutiques by Razny Jewelers, 900 North Michigan Shops, Shinola, Under Armour, Bloomingdale’s, and Roots.