Things You Might Not Know About Chicago

Chicago is often admired for its towering skyline, deep-dish pizza, and its historic contributions to jazz and blues. But beneath these widely known traits lies a city rich with unexpected details, cultural quirks, and fascinating legacies that even longtime residents may not know. This blog invites you to discover a more nuanced, surprising side of the Windy City—a metropolis layered in invention, resilience, and charm.

Many people assume that Chicago earned the nickname “The Windy City” because of the gusts off Lake Michigan. But the phrase originated in the late 19th century as a jab at the city's politicians and promoters, who were deemed to be full of hot air. Rival cities like Cincinnati used the term derisively, particularly during the competitive bidding process for the 1893 World’s Columbian Exposition. While the city is indeed breezy, the nickname is far more political than meteorological.

In 1885, Chicago revolutionized architecture when it unveiled the world’s first skyscraper: the Home Insurance Building. Standing a modest ten stories tall, it was the first building to use a steel-frame structure, making it significantly lighter and stronger than traditional masonry.

Although the original building was demolished in 1931, its innovation laid the foundation—literally—for modern high-rises around the world.

In one of the greatest feats of civil engineering, Chicago reversed the flow of the Chicago River in 1900. This project was undertaken to protect the city’s drinking water by preventing sewage from Lake Michigan contamination. Engineers accomplished this by constructing a canal that diverted the river’s flow toward the Mississippi. The reversal was so monumental that it remains one of the few man-made projects visible from space.

Chicago has a long legacy of innovation. Gideon Sundback, a Swedish-American engineer working in Chicago, was instrumental in developing the modern zipper in the early 20th century. Meanwhile, Edward Seymour and his wife Bonnie revolutionized DIY culture by inventing spray paint in the city in 1949. From fashion to art to industrial design, these modest-sounding inventions quietly transformed the world.

Chicago’s Pedway system is a little-known network of underground tunnels and overhead bridges that connects over 40 blocks in the downtown area. Spanning more than five miles, the Pedway is used by thousands of commuters daily, especially in the colder months. But even many locals are unaware of its full extent or the obscure shops, art installations, and secret corners hidden within.

The historic Route 66, also known as the “Main Street of America,” begins in downtown Chicago at the intersection of Adams Street and Michigan Avenue. While travelers often associate Route 66 with the deserts of Arizona or the hills of California, its journey starts amid the bustling energy and historic architecture of Chicago. This iconic road has played a pivotal role in American mobility and continues to attract road-trippers from around the globe.

Chicagoans wear their city flag with immense pride—literally. You’ll find it emblazoned on murals, t-shirts, even tattoos. Designed in 1917, the flag features four red six-pointed stars and two blue stripes symbolizing the North and South branches of the Chicago River. Each star represents a key historical event: Fort Dearborn, the Great Chicago Fire, the World’s Columbian Exposition, and the Century of Progress Exposition. This civic emblem resonates so deeply with residents that it's often mistaken for a national flag.

Before New York’s Broadway became the global standard, Chicago was already a booming theater town. In the early 20th century, it boasted more live theaters than any other U.S. city. Today, with institutions like The Second City, Steppenwolf Theatre, and Goodman Theatre, the city continues to serve as a cradle for dramatic innovation and comedic brilliance. Many top Hollywood and Broadway stars first graced the stage in Chicago.

While deep-dish pizza and Chicago-style hot dogs are internationally recognized, the city’s culinary offerings go much deeper. Italian beef sandwiches, jibaritos (Puerto Rican sandwiches made with fried plantains instead of bread), and Garrett’s caramel-and-cheese popcorn mix are all local treasures. The city is also home to an impressive array of Michelin-starred restaurants, experimental dining experiences, and food festivals that draw in gourmands year-round.

After the Revolutionary War, there were serious discussions about relocating the U.S. capital to a more centralized location. Due to its strategic position near the Great Lakes and its role as a transportation hub, Chicago was a strong contender. While Washington, D.C., ultimately prevailed, this historical footnote hints at just how vital Chicago was to the early ambitions of a growing nation.

Uncovering these lesser-known facets of Chicago reveals a city that thrives on history and culture, resilience, innovation, and community pride. Whether you’re looking to move into one of its vibrant neighborhoods, invest in historic architecture, or simply deepen your relationship with the city, having the right real estate guide can make all the difference.

For those looking to call Chicago—or anywhere in Illinois—home, Jerry Goodwin offers unparalleled insight, experience, and dedication. As a top Illinois real estate agent, Jerry understands the unique character of each neighborhood, from the legacy-rich streets of Hyde Park to the up-and-coming corners of Logan Square. His commitment to excellence and personalized service has helped countless clients navigate the complexities of buying and selling in the Chicago area.

Explore listings, learn more about Jerry’s approach, or get in touch to start your journey at jerrygoodwin.com. Discover the difference a knowledgeable and passionate local expert can make. Whether you're relocating, upgrading, or investing, Jerry Goodwin is your key to unlocking Chicago’s best-kept secrets—both on the map and in the market.