Best of the Grid Trolley Tour
Chicago’s street system is not just a monotonous grid of right angles. Northwestern University professor and writer Bill Savage reinforces that idea on this trolley tour that explores the history hidden in addresses that are on the wrong side of the street, roads that don’t run east-west or north-south, along with fascinating alleys, boulevards, bridges, and viaducts.
Recommended Shows (29)
Blues Bus Tour
Explore Bronzeville and the South Side to discover how America’s only truly indigenous art form was brought to Chicago during the Great Migration and evolved into its own distinct sound. Stops include Buddy Guy’s Legends, Pilgrim Baptist Church, and Chess Records. Meet at the Chicago History Museum. Tour runs about 4 hours and involves stair climbing.
Ride Ravenswood Bike Tour
Pedal through Ravenswood and Lincoln Square with writer and educator Sam Anderson-Ramos. Hear about how this bustling residential area founded in 1868 was once a manufacturing hub for industries such as Abbott Laboratories. Take in murals, tree-lined streets, and cultural spaces, including Dank Haus, Old Town School of Folk Music, and the Lillstreet Art Center. Tour meets in the plaza north of the Western Brown Line stop and runs approximately 2–2.5 hours. Participants must bring their own bike and helmet.
Pizza with the Hungry Hound Trolley Tour
Join ABC-7 food reporter Steve Dolinsky to explore three distinct styles of pizza: deep dish at Bebu, tavern-style at Side Street Saloon, and artisan at Labriola.
Chicago Herstory Trolley Tour
Join CHM educator Megan Clark on a trolley tour to find out more about the famous, infamous, and little-known women of Chicago who have left their indelible marks on the city.
Boystown Walking Tour
Queer femme historian Andie Meadows reveals how women, femmes, and transfolk helped shape Boystown, the country’s first officially recognized LGBTQ district.
Chicago's Fabulous Fountains Walking Tour
Join Greg Borzo, author of Chicago’s Fabulous Fountains, to explore this unique form of public art that unites water, stone, and steel. Stops include the Board of Trade Fountain, the Aon Center fountains, the Vietnam Veterans Memorial Fountain, and many more.
Union Station Walking Tour
Take a closer look at one of America’s last great railway terminals, which bustles with action day and night. Find out why it was once called a “city within a city” and learn the hidden stories that go unseen by thousands each day.
Over/Under the Chicago Loop Walking Tour
Turn the city upside down and inside out on a fun and zany tour with professional guide and comedian Margaret Hicks. Find the super-secret Pedway entrance into Millennium Park, travel from Upper Randolph to Lower Randolph to Lower-Lower Randolph, and discover excellent (and little-known!) views of the Loop from public buildings.
Ghost Hunt Trolley Tour
Discover the characters of nineteenth-century Chicago with Ursula Bielski, paranormalist and author of the newly released Haunts of the Devil. As you traverse the city by trolley, hear stories of famous evildoers such as H. H. Holmes and miraculous protectors like Father Damen whose prayers reportedly saved his church from the Great Chicago Fire.
Sacred Spaces Bus Tour
This annual holiday favorite returns! Join Rolf Achilles, professor of historic preservation at the School of the Art Institute of Chicago and author of Stained Glass in Houses of Worship, to explore some of Chicago’s most beautiful and non traditional sacred spaces.
Tour runs 3.5 to 4 hours and meets at the Chicago History Museum.
Above the City Train Tour
Explore the historic buildings and back porches of the North Side Brown Line on the city's most picturesque L line.
Movement of the People Train Tour
Discover the story of the Blue Line.
Graceland Cemetery Tour
Discover the remarkable stories of the Chicago elite buried in this famous cemetery. Featuring beautifully landscaped grounds and grand monuments, these walking tours led by historian Al Walavich reveal the history of the city's growth and its diverse inhabitants.
Gold Coast Walking Tour
Whisk away to a time when Chicago's rich and famous caroused on the coast.
Old Town Walking Tour
Step into the Old Town Triangle, where each structure has a story, from elaborate Queen Anne-style homes to balloon-frame cottages to the iconic St. Michael's Church.
Devil in the White City Bus Tour
Inspired by Erik Larson's best-selling book, go back to 1893 to follow the trails of Daniel Burnham and the devilish doings of H.H. Homes.
Leopold and Loeb Walking Tour
On May 21, 1924, a young boy went missing. The next morning, his father received a phone call informing him that his son had been beaten to death. This gruesome, senseless act stained Chicago’s history and still leaves many baffled. Tour the Kenwood neighborhood with author and historian Paul Durica, visiting the scene of the crime and other sites connected to the murder of Bobby Franks.
Meet at Forty-Ninth Street and Ellis Avenue. Walking tour runs 1.5–2 hours.
Bohemian National Cemetery: After Hours Walking Tour
Walk the grounds after the gates are locked. Bring your own flashlight or headlamp. Enter thru service drive at 5255 N Pulaski Rd. Approx 2 hours.
Garden of the Dead Walking Tour
Chicago’s early dead were trafficked into and out of its first municipal graveyard, the Chicago City Cemetery. Pamela Bannos of the Hidden Truths project shares stories of grave robbers, improper burials, and the confusion that led to the creation of Lincoln Park. Before midnight strikes, explore the gone-but-not-forgotten-history buried in the Museum’s backyard.
Meet at the Chicago History Museum. Bring your own headlamp or flashlight. Tours run 1.5–2 hours
Sheffield Stroll Walking Tour
Explore the history of the Sheffield/DePaul neighborhood, from its earliest German settlers to today's well-heeled residents.
Bronzeville Walking Tour
The Great Migration made its biggest impact on Chicago in Bronzeville, which became the center of African American culture from the 1920s through the 1950s.
Joe on the Go Coffee Trolley Tour
Find out what it’s like to be a master taster at a cupping demo, which is the practice of observing the flavors and aromas of brewed coffee. Tastings included.
Giants in the Park Bike Tour
Lincoln Park, historically Chicago’s great place of leisure, is sometimes compared to an outdoor art and history museum. Join Krista August, author of Giants in the Park, on a ride through this North Side playground and meet the heroes of our Chicago forefathers, celebrated in enduring bronze.
Playboy Walking Tour
The men's magazine that propelled the sexual revolution was first published in Chicago in 1953.
History Fun Run: Life & Style
This running tour features a variety of architectural styles and notable characters from Catholic cardinals to Playboy bunnies.
What The Lady Wants Walking Tour
Professional guide Wendy Bright’s tour of Marshall Field & Company brings together the history of Chicago’s landmark department store.
Pilsen Murals Walking Tour
Walk through Pilsen and get the larger meaning behind the artwork in Chicago’s capital of Mexican culture.
Augmented Reality: The Eastland Disaster
This interactive digital tour takes you to the site of the Eastland Disaster, the worst accident in the history of Great Lakes shipping.