How to Tour Chicago Like a Local

See the top family-friendly activities and attractions in Chicago, curated by a professional tour guide.

Meet Amanda Scotese:  She’s a professional tour guide in Chicago, who has a passion for local architecture. She’s been showing people around the Windy City since 2010, but her love of travel began nearly a decade earlier. “I actually got into being a tour guide in Italy. I had traveled there and a friend told me about the job,” she says. “That’s how I got my start: In Italy, working with groups of Americans.”

Amanda may have grown up in Kalamazoo, Michigan, but she always felt equally at home in Chicago. The two cities are a two-hour drive apart and her family is originally from the Chicago area. “As I traveled the world and came to know other American cities, I kept finding that no other city was quite as amazing as Chicago,” she says.

“Chicago is the world’s biggest small town,” Amanda says. “While there are all the amenities of a big city, there’s a personal feel to the city that I think is really different from other large cities around the world.”

Exploring Chicagoland: The Musts

Amanda says one of the most incredible things about Chicago is the architecture. “I would recommend the Loop Interior Architecture Walking Tour,” she says. “It highlights the most interesting elements of the city’s history and culture and gives people valuable insight into why Chicago is so famous for its architecture.” 

One of Amanda’s favorite stops in the entire city is the Chicago Cultural Center. It was built in 1897 as Chicago’s first central public library. The building features sparkling Tiffany mosaics and the world’s largest Tiffany stained glass dome. “You always see a mix of people there — people taking breaks from their downtown jobs, college students, families and seniors,” Amanda says. “It’s a truly public place in the city.” The building houses rotating exhibits on art and architecture, as well as free music, theater and dance performances.

While her tours focus primarily on the history and architecture of Chicago, there’s plenty to see and do outside the heart of downtown Chicago. Amanda always advises visitors to go out and explore the city’s different neighborhoods. “It’s where we live, and that’s where all the culture is.” To experience Chicago's local culture firsthand, Amanda recommends visiting these four must-see neighborhoods:

Cultural Center

Find Swedish Soul in Andersonville
Distance from downtown: About 30 minutes by car

One of the North Side’s most popular neighborhoods, Andersonville is known for its Swedish heritage. The quaint community was established by Swedish immigrants, and summertime visitors can thank this historical influence for Midsommarfest, one of the city’s most vibrant annual festivals. The neighborhood’s commercial center, Clark Street, is densely lined with small, locally owned businesses. Boasting eclectic boutiques, inviting bakeries and vibrant nightlife, Andersonville offers truly unique living, shopping and dining experiences.

A Mexican Culture Immersion in Pilsen
Distance from downtown: About 10 minutes by car

Amanda also suggests visiting Pilsen in the Lower West Side. It’s a popular destination for Mexican immigrants and Mexican-Americans alike. This neighborhood has been a colorful epicenter of Latin heritage since the 1960s, when many Latinos displaced by the expansion of the University of Illinois at Chicago found a new home in Pilsen. Because of the strong Mexican influence, visitors can expect authentic and flavorful cuisine. For example, Birrieria Reyes de Ocotlan is popular for its traditional goat stew.

A Taste of Germany in Lincoln Square
Distance from downtown: About 30 minutes by car

To experience German culture, drive to Lincoln Square in northern Chicago. The area boasts several traditional German businesses including the popular Gene’s Sausage Shop Delicatessen, Dank Haus German American Cultural Center and Merz Apothecary, which was founded in 1875. If exploring Lincoln Square works up your appetite, Amanda suggests refueling at the Chicago Brauhaus. “It’s a German-American tradition here to get a big stein of beer and a brat,” she says.

Lincoln Square

A Mind-Expanding Trip to Hyde Park
Distance from downtown: About 20 minutes by car

Amanda recommends venturing to the South Side to visit Hyde Park. “Hyde Park is absolutely gorgeous,” she says. Visitors will find the Chicago Museum of Science and Industry and the University of Chicago campus there. And when it comes to dining, the South Side has plenty to offer. “There’s a whole culture devoted to fast food that only exists on the South Side,” Amanda says. To get a taste, she recommends grabbing a breaded steak sandwich at Johnny O’s in the Bridgeport neighborhood, just north of Hyde Park.

Hyde Park
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About the Author

Amanda Scotese

Amanda Scotese is founder and executive director of Chicago Detours, a tour company for curious people. Visit her Vayable guide page for more information.