Chicago Gangsters, Crime & Prohibition: A Dark History Itinerary
No American city wears its criminal past like Chicago. This dark-history itinerary follows Al Capone, the Prohibition-era mob wars and the city's haunted corners — from bus tours of infamous gangster sites to speakeasy walks and after-dark ghost tours. Here is how to spend the day, with the best-rated tours to book for each.
At a glance
- 1Al Capone & mob bus tour
- 2Prohibition & speakeasy history
- 3Haunted Chicago after dark
- 4River North & the Loop on foot
Al Capone and the mob: a gangster tour
No city wears its criminal past like Chicago. A gangster tour — by bus or on foot — traces the world of Al Capone, the Prohibition-era mob wars and infamous sites like the Biograph Theater, where John Dillinger was shot, and the location of the 1929 St. Valentine's Day Massacre. Knowledgeable guides separate Hollywood myth from documented fact, and the bus versions cover ground across the North and South Sides that would take hours on foot.
Prohibition and the city's speakeasies
Chicago's mob money flowed through the speakeasies of the 1920s, and a prohibition tour brings that hidden world back to life. Guided walks and bus tours visit the sites of former gin joints and Loop watering holes, telling the story of bootlegging, corruption and the Volstead Act. Some experiences end in a modern speakeasy-style bar or dinner theatre with a period cocktail in hand — intimate, small-group tours that are popular, so book a few days ahead.
Haunted Chicago after dark
After dark, Chicago's history takes an eerie turn. Haunted walking tours and ghost cruises link the city's true-crime past to its most storied sites — the alleys of the old Levee district, Lincoln Park and the stretch of river tied to the 1915 Eastland disaster. Guides blend documented history with local legend, and the night-time setting makes the stories land. Evening ghost-and-gangster combos are a natural way to round out a day of dark history.
The neighborhoods where history happened
By day, the same stories live in the streets themselves. A history or neighborhood walking tour of River North, the Loop and beyond shows how the Great Fire, the World's Fair and waves of immigration shaped modern Chicago. Small-group tours of the North and South Sides pass the landmarks the crime tours mention, adding architecture, politics and everyday life. It is the best way to understand how the city that gave us Capone also gave us the skyscraper.
Book the experiences in this itinerary
Top-rated tours for exactly what this plan recommends in Chicago — prices per person.
