Uncover the darker, electrifying chapters of Chicago history — Prohibition speakeasies, Al Capone's empire, and the St. Valentine's Day Massacre — with a private expert historian on a cinematic walking and driving tour.
What to expect
Your historian-guide leads you into the South Loop, Streeterville, and the Gold Coast — neighbourhoods that witnessed Prohibition's most spectacular crimes. You'll stand outside the site of the Green Mill jazz club (still a working speakeasy), trace Capone's operational territory, and hear the true story of the 1929 massacre that shocked the nation. The guide weaves in the parallel narratives of immigrant communities, corrupt politicians, and jazz-age glamour that made 1920s Chicago the most fascinating city in America. Private vehicle tours extend the geography to Bridgeport and Pilsen. Utterly gripping for history lovers.
Good to know
Tours depart from central Chicago locations; confirm exact meeting point at booking. Private tours can be tailored to focus on Prohibition, the Great Fire, or the Civil Rights era. Book at least one week ahead. Tours run year-round; evening departures add atmospheric value.