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The History of Chicago Retail

At Innovative, we are fortunate to practice our art in a city with such a rich and inspiring retail history. Chicago has been a hub for innovation and commerce for centuries. For our upcoming Holiday 2024 Retail Audit, we visited downtown Chicago where it all began. 


Let’s talk about Chicago’s retail history and explain why we’re proud to be part of its thriving retail community.


Early Beginnings: Chicago as a Trading Hub

Chicago’s retail story begins in the early 1800s, when it was a busy trading post due to its strategic location along Lake Michigan and the Chicago River. As the city grew, so did its markets. By the mid-1800s, Chicago became a major trade center, and early marketplaces like the Randolph Street Market set the stage for what would become a retail powerhouse.


The Rise of Department Stores: 1800s to Early 1900s

The late 19th century saw the rise of iconic department stores like Marshall Field’s (founded in 1852), which set new standards for customer service and shopping experience. These stores helped put Chicago on the map as a leader in retail, combining luxury and accessibility, and changing how people shopped forever. 


Marshall Field's Staff, Early 1900s

The original Marshall Field's building, now Macy's on State Street, is a Chicago architectural landmark. Completed in 1907, it features the world’s largest Tiffany ceiling made of over 1 million pieces of glass in 6,000-square-feet.


Tiffany Mosaic Ceiling inside Macy's

Marshall Field's became famous not only for its architectural beauty but also for its legendary holiday displays. These festive displays, featuring intricate scenes and life-sized figures, became an annual tradition, enchanting both children and adults alike, and cementing the store's place in Chicago's holiday celebrations.


Malls and Modern Retail: 1950s-1990s

In the mid-20th century, shopping malls became central to Chicago’s retail landscape, with iconic centers like Water Tower Place (opened in 1976) offering a blend of shopping, dining, and entertainment under one roof. This era also saw the rise of Michigan Avenue’s Magnificent Mile, which attracted luxury brands like Chanel and Louis Vuitton.


As for the suburbs, Woodfield Mall, opened in 1971 in Schaumburg, Illinois, became another key shopping destination. At the time, it was one of the largest malls in the United States, with over 1.6 million square feet of retail space. Its success helped establish Schaumburg as a major retail hub.


Woodfield Mall, Opening Day 1971

Chicago Retail Today

Chicago continues to prove it can adapt to new retail trends, mixing high-end shopping with accessible, interactive retail experiences. But what makes Chicago unique is the history that lives on today. The Randolph Street Market is a celebrated monthly event, recognized as one of the top urban flea markets in the country. Woodfield Mall is still making headlines, including almost 30 million dollars in renovations in the past 10 years. Macy’s on State Street draws Chicagoans from every corner in the wintertime to see holiday displays that started at Marshall Fields over 100 years ago.


Macy's Holiday Displays

As for Michigan Avenue’s Magnificent Mile, flagship stores were heavily targeted during the 2020 riots. The last four years have seen several closures and relocations along "Mag Mile," especially in the technology vertical. However, we've also excitingly seen an influx of experiential retail and pop-ups such as the Museum of Ice Cream and the current Coach Pop-up. 


Today, retail hubs continue to thrive both in the city and in the surrounding suburbs. The spirit of innovation, creativity, and resilience continues to define Chicago's retail scene.


Why We're Grateful to be Here


What makes practicing the art of retail in Chicago truly special is the city’s vibrant, supportive retail scene. 


From its rich retail history to its cutting-edge future, Chicago offers an inspiring environment for our team to thrive. We’re grateful to be part of this legacy and excited for the future of retail in such a dynamic, forward-thinking city.

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