Historic Chicago Tour

As with any great city, Chicago inspires its share of myth and lore. Travelers can get the inside scoop on what’s real and imagined from longtime city tour guides. Did you know that Chicago is home to the third largest Chinatown in America? That the city underwent its first urban renewal program more than 100 years ago? And that it didn't really earn its "Windy City" nickname because of the weather? Walk this way for more city surprises and tips. 

Chicago Greeter Program
You don't need to pay a bundle for a tour of Chicago. Through the city's free Chicago Greeter Program, get a personalized tour of the city from a local volunteer. The most popular tour option is the "Greeter's Choice,” where a volunteer greeter leads visitors through popular city sections. This is a unique opportunity for visitors to get personal tours of Chicago attractions such as the Crown Fountain in Millennium Park, a pair of 50-foot towers made with 10,000 glass bricks. 

Chicago Cultural Center
Rich in history, the Chicago Cultural Center is a good place to start your journey, says Ed Mazur, a tour guide with the city's Chicago Greeter Program. The center features the world’s largest Tiffany glass dome, plus a room that once served as the meeting place of the Grand Army of the Republic (an association of Civil War veterans). Columns in the center's Preston Bradley Hall detail in gold leaf frieze the names of key Civil War battles. The building also offers great views from the top floor of Millennium Park, the public park near Lake Michigan.

Chicago’s Architectural Greats
Here's something that may surprise you -- given how long ago it was. "Chicago had its first urban renewal program in 1871," says Mazur, a former Chicago history and politics professor at the University of Illinois. "Of course, that's because the Great Chicago Fire happened in 1871," he adds. In the years to come Chicago rebuilt, becoming home to skyscrapers such as the iconic Willis Tower (formerly the Sears Tower), the famous Wrigley Building and the groundbreaking Chicago Building, whose steel-frame construction showcased what would become known as the Chicago school of architecture. Mazur recommends using Chicago Transit Authority’s buses and trains to get around. In fact, Mazur notes, the Chicago Greeter Program offers visitors free 1-day CTA passes. 

Chicago’s Ethnic Neighborhoods
Did you know Chicago boasts the nation’s third largest Chinatown, after NYC and San Francisco? Get a flavor of the world created by these immigrants at Chinatown Market on Archer Avenue and noodle and dumpling shops such as Joy Yee's Noodle Shop on South China Place. For Greek flavor, head to Chicago's Greektown, on North Halsted Street, by West Adams Street. Established in the 1840s, Greektown is filled with grocery stores selling Greek foods such as gyros and spanakopita. Chicago's Little Italy on the city's west side is home to the Holy Guardian Angel, Chicago's first Italian congregation and the National Italian American Sports Hall of Fame. Italy lovers can also swing by Conte di Savoia for Italian imports like coffee and olive oil.

Chicago, From Up High
Taking in Chicago's famous skyscrapers from up high can come at a premium; some buildings charge an observatory entrance fee as high as $31. But city insiders know that your money could be far better spent on a tasty meal, overlooking 360-degree views of the city. "The John Hancock Building has a restaurant [Lavazza Expression Café] on the 95th floor," says Mazur. "And the Trump Tower’s has a restaurant [Sixteen] on the 16th floor that overlooks the Chicago River and Lake Michigan."

Now, about Chicago's Windy City nickname: It was actually inspired by the “hot air” blowing from the mouths of city politicians. You'll get the inside scoop on fun facts like these as you dive into Chicago’s towering past.

Valerie Conners is a freelance writer and editor who has worked for media outlets such as the Travel Channel, Discovery Channel, Animal Planet, Boston Globe, Philadelphia Inquirer and Frommer's Travel Guides.