These 5 Chicago history tours will show you a different slice of the city
In a city with a history as rich as Chicago’s, summertime is full of opportunity to explore outside your neighborhood, fire up your kids’ summer brains or simply try something different.
This list presents you with options.
Head underground … and watch for rats
Why go on a walking tour that openly plugs rats? Because those critters own this city just as much as we do. For proof — and to earn a new appreciation for our fellow citydwellers — sign up for local tour guide Mike McMains’s “Underground Chicago (Plus Rats!) Tour," a 90-minute exploration of the city under the city. Departing from the Mag Mile and quickly descending into the lower regions and underbelly of the city, it’s an educational way to learn something new about Chicago, entertain guests hankering for a tour or simply avoid the hot summer sun. $30, 90 minutes, tourswithmike.com.
Stroll the Jaffee History Trail
If you haven’t taken the time to explore the Jaffee History Trail, which opened in 2021 just east of the Chicago History Museum, put it on your list. Encompassing 4.5 acres of landscaped grounds planted with native pollinators, the little trail features eight informative stops with representations of the city’s history — from the giant hunk of metal discovered in the museum’s back yard to the infamous Couch Tomb. Free; explore at your own pace; daily; chicagohistory.org/exhibition/jaffee-history-trail.
Take a bus tour with Dilla
Most locals know Auburn Gresham–based historian Sherman “Dilla” Thomas from his viral TikTok videos proving “everything dope about America comes from Chicago.” But have you ever taken one of his neighborhood tours? Book tickets and board the bus for one of Dilla’s Mahogany Tours through neighborhoods on the South and West sides such as North Lawndale, Englewood or Bronzeville. $45, durations vary; weekends; chicagomahogany.com.
Learn about a seminal architectural style
If you pay any attention to residential buildings in older parts of town, you may be familiar with the typical workers cottage: small, 1½-story homes built for working-class families between the 1880s and 1919. Across the city, there are nearly 60,000 of these homes, but they’re rapidly being demolished. Enter the Chicago Workers Cottage Initiative, a small group who organized in 2021 to celebrate these little houses and preserve them from demolition. During the warmer months, the group occasionally leads informative, intimate tours of neighborhoods with a lot of workers cottages such as McKinley Park and Logan Square. Donation, 90 minutes; weekends; workerscottage.org.
This photo shows an aerial view after the first atomic explosion at the Trinity Test Site near Alamogordo, N.M., on July 16, 1945. Trinity Site, a designated National Historic Landmark, only opens to the public twice a year. But the University of Chicago campus also played a vital role, and visitors can walk a historical route there nearly any day of the year.
AP Photo, File
Dig into the city’s love affair with film
Yes, we know about the Art Institute’s Ferris Bueller’s Day Off tour — but this one’s better. “From Fairgrounds to Film Set: Chicago’s Midway, Movies, and the 1893 World’s Fair” starts from the Midway Plaisance, whose ties go back to the World’s Fair, then winds along the tree-lined streets of Hyde Park to showcase five stops tied to the movies. It’s worth your time just to stroll through the leafy University of Chicago campus, and you’ll walk away with a new appreciation for our city’s role in the film industry. $29.99, 75 minutes; chicagomovietours.com.
Want to take your own film-related tour? Stream the Oscar-winning movie Oppenheimer, then take this self-led tour of the relevant atomic sites on the campus of the University of Chicago.
Lauren Viera has covered Chicago’s arts and cultural scenes for more than 20 years. She is the author of "The 500 Hidden Secrets of Chicago" (Luster) and lives in Logan Square.