Walk the streets where Al Capone once moved and discover Chicago’s Prohibition-era underworld on a focused, one-hour guided tour. Expect a mix of archival history, urban geology, and clear directions on where to look and why it mattered.
More ways to explore the area's outdoor wonders
A brisk spring wind off Lake Michigan cuts through Michigan Avenue as your guide gathers the group outside the South Garden of the Art Institute. Voices drop as the city’s polished facades give way to stories of speakeasies, backroom deals and the crackle of Prohibition-era radios; pavement becomes a timeline where each corner keeps a secret.
Difficulty
easy
Duration
1 hour
Fitness Level
Suitable for most fitness levels; requires standing and walking for the duration
Wildlife
History
Chicago’s gangster era peaked during Prohibition (1920–1933), when bootlegging and organized crime reshaped local politics and business.
Conservation
This tour emphasizes respectful tourism and preservation of historic façades; avoid touching or climbing on older masonry to protect fragile architecture.
Reserve your spot on the Gangs and Mobsters Crime Tour at Chicago today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Meet at the South Garden
Arrive 10–15 minutes early at the Art Institute’s South Garden; guides wear white Junket shirts, so you’ll find them easily.
Wear supportive footwear
Paved sidewalks and a steady one-hour pace favor sturdy walking shoes over dress shoes or sandals.
Hydrate, especially in summer
Carry a small water bottle—Chicago humidity can make an easy walk feel much hotter in July and August.
Use public transit to avoid parking hassles
Several bus and El stops are nearby; public transport is often faster than parking downtown.
Supportive walking shoes
Paved urban sidewalks and a steady pace require comfortable, grippy footwear.
Light jacket or windbreaker
Lake Michigan breezes can be chilly in spring and evenings.
spring
Reusable water bottle
Staying hydrated keeps you attentive during summer tours.
summer
Portable phone charger
Useful for photos, maps and saving digital tickets