10 Best Shopping Spots In Chicago, Illinois

shopping in chicago
Ryan Joshua
Ryan Joshua 
| 4 min read

Known as the Windy City, Chicago is regarded as the largest yet the most lively city in the whole United States. Everyone surely feels at home when they live in the city. The city surely has much to offer everyone in its high-rise buildings and skyscrapers, affluent streets, and many more places of interest. The city also boasts of its very posh shopping spots that has become a haven for shopaholics. The streets of Chicago is lined with a lot of sophisticated boutiques from the world’s biggest brands. Keep on reading and get to know the best places to shop in Chicago, Illinois.

1. Loop

Chicago L in the Loop
Source: Photo by Wikimedia Commons user FTSKfan used under PUBLIC DOMAIN

The Loop is considered as Chicago’s official downtown area and is one of the most important business districts in the world. Aside from its very unique and modern architecture plus its very busy environment, this urban jungle has the most number of cultural attractions, urban park areas, superb restaurants, and a haven for shopaholics.


Address: Community Area 32, Chicago, IL

Website: Loop

Visited this place?

2. Lincoln Square

Willis Tower Seen From Lincoln Square - panoramio
Source: Photo by Wikimedia Commons user Colin Andersen Ph... used under CC BY-SA 3.0

Lincoln Square is where Chicago’s rich history and the modern times merge into a single location. There are still some areas in Lincoln Square that feature traditional German dining halls and some European-style architecture. But aside from those historical, old-fashioned shops and streets made from cobblestone, Lincoln Square boasts of its unique array of restaurants, bars, boutiques, and other places of interest.

Lincoln Square

Address: Lawrence, Western and Lincoln Avenue, Chicago, IL

Website: Lincoln Square

Visited this place?

3. State Street

Macy's State Street
Source: Pixabay

State Street is the Loop’s main shopping district. From designer brands to specialty shops that are rare finds, State Street surely has something for you. Macy’s on State Street, the world’s second largest department store, can be found here. You’ll surely shop ‘til you drop in their whopping eight-floor building filled with amazing apparel, accessories, and home furnishings.

State Street

Address: State Street, Chicago, IL

Visited this place?

4. Maxwell Street Market

Maxwell Street Market
Source: Pixabay

The Maxwell Street Market features all of Chicago’s best bargains from all over the world. It has an amazing mix of merchandise and some of the best Latin and Mexican street foods in Chicago. You get to buy all sorts of things–from tools, dresses, toys, home items, and many more–at an amazing price.

Maxwell Street Market

Address: W Maxwell St, Chicago, IL

Website: Maxwell Street Market

Opening hours: Sun: 9am - 4pm (closed Mon - Sat)

Visited this place?

5. Magnificent Mile & Streeterville

20070513 Magnificent Mile
Source: Photo by Wikimedia Commons user TonyTheTiger used under CC BY-SA 3.0

The Magnificent Mile in Chicago has a myriad of activities for you to see and do and that includes Chicago’s best attractions and landmarks. Shopping is truly vibrant in the Magnificent Mile with its more than 460 stores that are open to serve you. The stores are very diverse and includes popular brands, major department stores, international luxury brands and designer labels, and some vertical shopping malls. Some of the most popular stores include 900 North Michigan Shops, Water Tower Place, and Saks Fifth Avenue.

Magnificent Mile

Address: North Michigan Avenue, Chicago, IL

Website: The Magnificent Mile

Visited this place?

6. River North

River North Neighborhood, Chicago, Illinois (9179467083)
Source: Photo by Wikimedia Commons user Ken Lund used under CC BY-SA 2.0

River North is one of Chicago’s most affluent neighborhoods. With its proximity to the Magnificent Mile and the Loop, River North is one of the places where you can go see some fine art. It is home to the famous and massive Merchandise Mart, together with several trade showrooms that furniture and design aficionados flock to.

River North

Address: River North, Chicago, IL

Website: River North

Visited this place?

7. Andersonville

Andersonville, Chicago
Source: Photo by Wikimedia Commons user Zagalejo used under PUBLIC DOMAIN

Andersonville is regarded as home to one of the city’s biggest gay and lesbian communities. Known for its diversity with a bizarre environment yet unique flavor, the area is now rapidly becoming one of the North Side’s most popular neighborhoods. The area boasts of its several art stores, community diners, and restaurants.


Address: Lawrence Street, Chicago, IL

Website: Andersonville

Visited this place?

8. Bucktown and Wicker Park

Wicker Park
Source: Photo by Wikimedia Commons user Nitram242 used under CC BY 2.0

The Bucktown and Wicker Park area is regarded as one of the centers of Chicago arts and creations. The neighborhood has been known to be the go-to place for live music, nightlife, dining spots, and art galleries. There’s also a very nice array of vintage and old-fashioned shops, small boutiques, and luxurious establishments with items for home and beauty.

Bucktown and Wicker Park

Address: N Damen Ave, Chicago, IL

Website: Bucktown and Wicker Park

Visited this place?

9. Oak Street

Having a great contribution to the Chicagoan history because of the Chicago fire of 1871, a lot of wealthy citizens moved to Oak Street and built their European-inspired homes and mansions. But now, the historical Oak Street has combined modernity with its rich history. It is now the center of beauty in Chicago and is also known as the “most prestigious shopping street in Chicago”, with its array of boutiques and salons which are regarded as the best in the world. Indeed, Oak Street is recognized as the street of the rich and the sophisticated. Some of the most well-known shops along Oak Street include Barneys New York, Chanel, Giorgio Armani, Dior, Hermes, Jimmy Choo, Dolce and Gabbana, Prada, Marc Jacobs, Yves Saint Laurent, and Versace.

Oak Street

Address: Oak Street, Chicago, IL

Website: Oak Street Chicago

Visited this place?

10. Gurnee Mills

Gurnee Mills wide
Source: Photo by Wikimedia Commons user Interiot used under PUBLIC DOMAIN

Known as the largest outlet and value shopping in Illinois, Gurnee Mills offers more than 200 stores for you to choose from. Shop ‘til you drop at stores such as Macy’s, Neiman Marcus Last Call, Saks Fifth Avenue OFF 5TH, Forever 21, Kohl’s, Bed Bath & Beyond, Buy Buy Baby, and Bass Pro Shops Outdoor World. Dine after you shop at great restaurants like Rainforest Cafe and be entertained at the Gurnee Marcus Cinema, ice skating, miniature golf, and laser tag.

Gurnee Mills

Address: 6170 W Grand Ave, Gurnee, IL

Website: Gurnee Mills

Opening hours: Mon - Sat: 10am - 9pm; Sun: 11am - 7pm

Visited this place?

Shop 'til you drop while in Chicago

With all of these shopping districts all around Chicago, you will surely have everything you want while you are in the city. For all of you shopaholics out there, make sure to pay a visit to these great shopping areas while you’re in Chicago!

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Ryan is a Computer Engineer with a heart for traveling and writing. Born in Pasay City, Philippines, and raised in Melbourne, Australia, he is now based in the Philippines' City of Smiles, Bacolod...Read more

 Want to contribute as a Local Expert?
Explore Chicago
Looking for accommodation?
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.