Photos by Aaron Watts

By Jackson Greenleaf, Staff Writer

Chicago is famous for its deep-dish pizza, the dominance of Michael Jordan and the Bulls, and its status as the hometown of the first African American U.S. President, Barack Obama. But beyond these cultural staples, another aspect of the city that deserves praise is its vast architectural lore and diverse construction styles.

The Great Chicago Fire of 1871 produced a new era of architecture, driven by necessity and reinvention. The city had become a playground for some of the greatest architects in history, including Louis Sullivan, Daniel Burnham, and Frank Lloyd Wright. These visionaries turned the Windy City into a beacon of modern design, giving birth to the skyscraper and establishing Chicago as a world leader in architectural excellence.

The story of Chicago’s architecture is not just about the buildings themselves, but also about the people who designed, built, and lived in them. It’s a story of diversity and innovation, as the city continually pushed the boundaries of what was possible.

From the iconic Willis Tower (formerly Sears Tower) to the modernist brilliance of the John Hancock Center, Chicago’s skyline is a testament to the city’s enduring architectural legacy. I was able to experience this rich history from a Chicago river cruise tour. Recognized three years in a row as one of the best boat tours in North America by the USA Today Readers’ Choice Awards and named the Best Tour in 2023 by the Chicago Reader, the Chicago Architecture Center River Cruise aboard Chicago’s First Lady offers a beautiful perspective on the city’s architectural triumphs. The success of this great tour can be attributed to its guide and main architectural expert, Harold Hirsch, a Chicago native currently living in Evanston, Illinois. Hirsch’s passion for the city’s history and architecture is illuminating.

A lifelong Chicagoan, Hirsch’s connection to the city runs deep.

“I’ve always been interested in history and geography,” he shared. “When I was a kid in the 40s, I used to travel by myself on the streetcar around the city, just learning new parts of the city.”

Hirsch’s expertise isn’t just limited to the well-known structures that dominate Chicago’s skyline. He brings to light hidden gems and lesser-known areas of the city that are often overlooked.

“Garfield Park and the Garfield Park Conservatory are wonderful, but people don’t go there because they’re afraid of the West Side,” Hirsch noted.

His insights add layers to the tour, giving participants a broader understanding of Chicago’s architectural and cultural landscape. The cruise offered a comprehensive overview of Chicago’s architectural evolution. It’s more than just a sightseeing tour; it’s an educational journey through the city’s history, offering insights into how Chicago’s skyline came to be and the cultural and historical context that
shaped it.

As you sail along the Chicago River, you’ll see the city from a perspective that few others experience. The stories of these buildings are not simply tales of brick and mortar, but of human ambition, creativity, and the relentless pursuit of progress. In Chicago, the skyline is like a canvas, with each building serving as a brushstroke in the masterpiece that is the Windy City.