City guides

Best places to shop in Chicago

Discover the top shopping destinations in the Windy City that cater to every style and budget.

September 19, 2023
 min read
Last updated:
Jan 15
A view of the Chicago skyline, with the Chicago river in the foreground.

Chicago, with its rich history and vibrant culture, is also a shopper's paradise. From luxury boutiques to quirky local stores, the city offers a shopping experience like no other. Let's dive into some of the best places to indulge in retail therapy in Chicago.

Woodfield Mall

Located just a short drive from downtown Chicago, Woodfield Mall is a sprawling shopping complex that offers a diverse range of retail options. From high-end luxury brands to popular high-street names, this mall caters to every shopper's needs. The architecture is modern, with spacious walkways and a plethora of dining options to refuel after a long shopping spree. Whether you're looking for the latest fashion trends, tech gadgets, or unique home decor, Woodfield Mall promises a delightful shopping experience. 


Andersonville is not just a shopping destination; it's a journey into Chicago's rich cultural tapestry. This historic neighborhood is known for its Swedish heritage, and this influence is evident in the local boutiques and eateries. As you stroll through the tree-lined streets, you'll come across stores selling handcrafted goods, vintage clothing, and artisanal food products. The vibe here is relaxed and community-driven, making it a perfect spot for those who prefer a more intimate shopping experience. Don't forget to stop by a local cafe and savor some Swedish delicacies! 

River North

River North is the epitome of urban chic. This upscale neighborhood is a melting pot of art, fashion, and culture. The streets are lined with art galleries showcasing contemporary works, designer boutiques offering the latest trends, and chic cafes serving gourmet delights. If you're someone who appreciates the finer things in life, River North is the place to be. The area is also known for its vibrant nightlife, so after a day of shopping, you can unwind at one of the many trendy bars or restaurants. 

State Street

State Street is often referred to as the "heart of Chicago's shopping scene." This bustling street is a blend of historic charm and modern retail. The iconic Macy's building stands as a testament to the area's rich history, while the plethora of other retail outlets cater to the modern shopper's needs. From fashion to electronics, books to beauty products, State Street offers a comprehensive shopping experience. And when you need a break, there are numerous eateries where you can grab a quick bite or indulge in a gourmet meal. 

Fashion Outlets of Chicago

For those who love branded goods but also love a good bargain, the Fashion Outlets of Chicago is a dream destination. Located in Rosemont, this outlet mall houses some of the biggest names in fashion, all offering their products at discounted prices. The mall's sleek and modern design makes for a pleasant shopping environment. And with a range of dining and entertainment options, it's easy to spend an entire day here, hunting for the best deals and taking breaks in between to relax and refuel.

The Magnificent Mile

The Magnificent Mile, often referred to as "Mag Mile," is Chicago's premier shopping district. Stretching along Michigan Avenue, this bustling boulevard is a blend of historic architecture and modern skyscrapers. It's home to some of the world's most renowned luxury brands, making it a haven for fashion enthusiasts. But it's not just about high-end shopping; the Mag Mile also offers a range of dining, entertainment, and cultural attractions. The historic Water Tower, one of the few structures that survived the Great Chicago Fire, stands as a symbol of the city's resilience. As you walk along the Mag Mile, you'll be treated to stunning views of the Chicago River, making the shopping experience even more memorable. 

Water Tower Place

Water Tower Place is more than just a shopping center; it's an iconic landmark in Chicago. Situated on the Magnificent Mile, this multi-level mall offers a curated selection of brands, catering to a diverse clientele. The mall's atrium design, with its glass elevators and cascading water features, adds to the overall shopping experience. Apart from retail outlets, Water Tower Place also houses theaters, restaurants, and even a hotel. Whether you're in the mood for some serious shopping or just want to enjoy the ambiance, Water Tower Place promises a delightful experience. 

Oak Street

Tucked away from the hustle and bustle of the Magnificent Mile, Oak Street is Chicago's luxury shopping destination. This tree-lined street is home to some of the world's most exclusive brands, from fashion to jewelry. The shopping experience here is intimate, with boutiques offering personalized services to discerning clients. But Oak Street isn't just about shopping; it's also a cultural hub, with art galleries and theaters dotting the landscape. After a day of indulgence, you can relax at one of the many upscale restaurants or cafes that line the street. 

Merchandise Mart

Merchandise Mart is a testament to Chicago's architectural prowess. This massive building, spanning two city blocks, was once the largest building in the world. Today, it's a hub for design and commerce. Housing showrooms for everything from furniture to fashion, Merchandise Mart is a must-visit for design enthusiasts. The building also hosts various trade shows and events throughout the year, making it a buzzing center of activity. With its Art Deco design and rich history, Merchandise Mart offers a shopping experience that's truly unique. 

Hyde Park

Hyde Park, located on Chicago's South Side, is a blend of history, culture, and commerce. This neighborhood, best known as the home of the University of Chicago, offers a diverse shopping experience. From independent bookstores to boutique fashion outlets, Hyde Park caters to a range of tastes. The area is also rich in history, with landmarks like the Robie House and the Museum of Science and Industry. As you shop, you'll also get a glimpse into Chicago's academic and cultural heritage, making Hyde Park a destination that offers much more than just retail therapy.

Chicago's shopping landscape is as diverse as its cultural tapestry. Each destination, from the bustling streets of the Magnificent Mile to the serene lanes of Hyde Park, offers a unique experience. So, the next time you're in the Windy City, make sure to explore these shopping hotspots and immerse yourself in the city's vibrant retail scene.


*Prices fluctuate based on season and day of the week.

In this article:

Share article

You may also like


Super is dedicated to helping people get more out of life by providing them with ways to build credit, save money, travel more, and earn cashback rewards.