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Summertime doesn’t have to mean taking a break from learning. Here are some of the best walking tours for taking in Chicago history, including a jaunt from the Chicago Workers Cottage Initiative.

Courtesy of Tom Vlodek/Chicago Workers Cottage Initiative

These five Chicago history tours will show you a different slice of the city

This summer, brush up on your local history with tours that highlight everything from architectural styles to underground critters.

In a city with a history as rich as Chicago’s, summertime doesn’t always have to mean taking a break from learning.

Whether you want 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. Next tour is July 6.


The Jaffee History Trail features eight informative stops with facts about the city’s history.

Courtesy of the Chicago History Museum

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 this summer. 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.


Chicago historian Shermann “Dilla” Thomas speaks to local high schoolers playing in the Double Duty Classic baseball game during a bus tour in 2023 in Chicago.

Owen Ziliak/Chicago Sun-Times

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.

Chicago Workers Cottage Initiative 3.jpeg

The Chicago Workers Cottage Initiative leads informative tours of cottage-heavy neighborhoods such as McKinley Park and Logan Square.

Courtesy of Tom Vlodek/Chicago Workers Cottage Initiative

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, 1 1/2-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 of people who organized themselves in 2021 to celebrate these little houses in attempts to preserve them from demolition. During the warmer months, the group occasionally leads informative, intimate tours of workers cottage-heavy neighborhoods such as McKinley Park and Logan Square. Donation, 90 minutes. Weekends.

This photo shows an aerial view after the first atomic explosion at the Trinity Test Site near Alamogordo, N.M., on July 16, 1945. Chicago's role in the atomic race gets a bit part in the movie Oppenheimer.

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 UChicago 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. Next tour is June 30.

Want to take your own film-related tour? Stream the Oscar-winning movie Oppenheimer, then take this self-led, WBEZ created 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.

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