Explore the highlights of Chicago’s Chinatown in just 90 minutes with our expert-guided History and Culture Tour. This tour takes you through iconic landmarks, historic streets, and cultural sites, sharing authentic stories and ... More

Get a closer look into how alcohol flowed through the streets of Chicago! From the “down and dirty” gangster hangouts, to the “jackets required” establishments for Chicago’s elite, learn what it took for all Chicagoans t... More

Go beyond Capone. An expert guides uncovers the Beer Wars, the ambushes, and the brutal rivalries on these exact streets.... More

Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “Murder in The Chicago Loop” transports you to the year 1923. You are a detective in Chicago and a woman has been found murdered... More

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once seemed as though the stunning architectural details of Chicago's Old P... More

The streets of Chicago hold clues to a chilling murder. Can you piece together what happened on this self-guided walking quest? Your smartphone delivers clues, witness statements, and puzzles as you navigate between real-world loc... More

An amazing, local's guided tour of one of Chicago's coolest neighborhoods. Learn the history and get advice from a local who knows this area and make your Chicago experience a memorable one. Get out of downtown, come and experienc... More

We wrote the book(s) on Chicago ghosts! Now in our 26th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's haunted history over more than two decades. Chicago Hauntings is the original Chicago... More

Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour through downtown Chicago, you’ll hear untold stories of Black excellence, resilience, and activi... More

Take a time travel journey inside Chicago's best-kept secret: a 125-year-old architectural marvel. This extraordinary building was envisioned by renowned architect Solon Spencer Beman, famous for designing the town of Pullman and ... More

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant city at your own pace. Begin at Millennium Park where Anish Kapoor's Cl... More

Uncover the essence of Chicago's sports culture on this guided tour through the downtown area. Learn about the city’s iconic sports figures, explore fascinating stories, and discover the hidden sports landmarks that define the l... More

We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explorations for high school students, to tavern tours tracing Chicago’s ... More

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians w... More

This private historical ghost walking tour in Chicago explores stories rooted in the city’s layered past. You will walk through Lincoln Park, an area shaped by transformation from cemetery grounds to residential district. What t... More

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour small group (12 Guest Maximum) guided walking tour is perfect f... More

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the first Europeans to come through here, the Great Chicago... More

Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden gems and untold stories that shaped the city’s cultural heart. Bo... More

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a little bit of culture, some amazing architecture, & a ton of great photos then this is the tour ... More

This private architectural walking tour in Chicago explores residences that reflect the city’s design evolution. You will begin along Lake Shore Drive, where early high-rise living reshaped urban life. What architectural movemen... More