Trace a century of daring architectural gambles in Chicago's Loop. From six-foot brick walls to soaring glass curtain walls, discover how engineers conquered swamp soil, roaring fires, and howling winds to invent the modern skyscr... More

Enjoy a private, fully personalized sunset tour along Chicago’s scenic lakefront. Travel in comfort with your English-speaking driver, who shares insights into the city’s architecture, skyline, and history while guiding you to... More

Winner of 10 Best History Tours by USA Today in 2026, and the "ORIGINAL" Chinatown tour since 2001. Discover the history, culture, and hidden stories of Chicago’s Chinatown on a guided walking tour through one of the city’s ... More

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Englewood, led by Historian Dilla, who uncovers the unique stories and contributions of these communities,... More

Uncover the chilling history of Chicago's gangsters and ghosts on this thrilling late-night Halloween walking tour. Delve into the dark secrets of the South Loop, once a vice district, as your historian guide shares captivating ta... 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

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy to customize the tour itinerary and content for your group. Discover the amazing hist... More

Bucktown has a knack for keeping secrets - and most of them are deeply unsettling. On this self-guided walking tour, you'll hear the true stories behind the neighborhood's murders, hauntings, and disappearances, encountering a rea... More

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Chatham, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, p... More

Discover Hollywood magic in the heart of the Midwest on the Chicago Suburbs Movie Sites Tour. Visit real filming locations from classics like Ferris Bueller’s Day Off and Home Alone to modern hits like The Dark Knight. Led by a ... More

Explore Chicago with a passionate local guide on a small-group walking tour that takes you beyond the city's most recognizable landmarks. As you stroll through the heart of the city, you'll uncover fascinating stories, admire worl... More

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always accurate. On this tour, you’ll hear how the culture in turn-... More

Visit the most beautiful interiors in Chicago with a local guide bringing their stories to life. Step into stunning centuries-old architecture on a guided walking tour of downtown Chicago. We go in buildings no other walking tou... 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

The route to Lake Geneva follows the incredible coastline of Lake Michigan and eventually into the rolling green hills of Wisconsin. Your group will stop to see landmarks such as the Gold Pyramid House and the stunning Bahāʾī t... More

Turn heads and take in the views with your Premier Chicago Tour Experience! Your journey begins in the passenger seat of an automotive masterpiece. Tour downtown Chicago in an Exotic Sports Car where you'll discover the luxury b... More

On this private walking tour our expert local guide will take you to see some of Chicago’s best-known attractions! The day will begin with you meeting with your friendly local guide at Millenium Park, home to Cloud Gate.From t... More

Explore the festive charm of Chicago during the holiday season on a double-decker bus tour showcasing the city's dazzling lights. This BYOB tour allows you to sip your favorite beverages while taking in iconic holiday displays, fr... More

This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the neighborhood’s transition from a wealthy enclave to a gritty artist ... More

With over 10 years of birding, Wayne can not only identify birds out in the wild through sight, but also through their many calls! Interested in starting out with birding? Maybe you're visiting for a day and looking for a specific... More