Chicago’s Loop is home to some of the city’s most perfectly preserved Art Deco architecture designed during the Roaring 20s. See 7 stunning Art Deco buildings, all masterpieces in their unique & individual ways, as well as 4-5... 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

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

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

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

Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets our tour apart is the seamless blend of three iconic destinations—the P... More

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through Chicago’s most illustrious addresses, where each step tells a story of architectural brilliance, historical grandeur, and cultur... More

Skip the crowds this is a private tour for your group only! “Lincoln Park Spirits: A Ghostly Walk Through Chicago’s Past” takes you on an eerie exploration of the Lincoln Park neighborhood. Begin at Julia Porter Park, a sere... More

Step into the eerie past of Chicago on this thrilling 2-hour private ghost tour led by a local through the haunted corners of the Lincoln Park area.... 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 Chicago’s bold spirit through its iconic landmarks, from the Gothic Holy Name Cathedral to the gleaming Cloud Gate. Hear untold stories of resilience, art, and innovation. Optional: see the Chicago Theatre, Cultural Cent... More

Explore Chicago's iconic skyline on this enlightening Riverwalk architectural tour. Experience the rich tapestry of history and innovation as "you get your steps in" along the scenic Riverwalk, revealing the stories behind the cit... More

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through the Loop’s architectural wonders with our Loop Architecture Tour in Chicago. Explore the iconic Chicago Board of Trade Building ... More

Immerse yourself in the vibrant food culture of Chicago with a guided walking tour, led by a knowledgeable local guide. Traverse Downtown's diverse culinary landscape, tracing the influence of immigrants on the city's gastronomy. ... More

Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’s spirit to life—one ste... More

Looking for something truly local, active, & unforgettable for your kids while you explore Chicago? Bobby’s Chicago Kids Camp is a one-of-a-kind day camp Chicago experience designed with both visiting families and locals in mind... More

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour circles Wicker Park, showcasing stunning Victorian mansions o... More

Explore the underground drinking culture of Chicago during the Prohibition era on this captivating app-guided walking tour. Uncover the secrets of hidden bars and speakeasies while learning about the city's notorious figures like ... More

Discover the local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit built to meet your style and wishes. Learn more about the art of styling your body features and ta... More