5.0 ★ · 411 reviews · from USD35
Walk in the footsteps of Al Capone, John Dillinger, and real life ghost stories while hearing tales of Chicago's haunted past. Visit Prohibition Era speakeasy bars, sites of real life mob shootouts, and haunted tragedies that shape the city's legacy. This walking tour blends ghost stories, true crime history, and architectural landmarks to reveal the beauty and horror from one of America's most famous time periods, right where it happened. You'll gain special access to architectural interiors tied to famous history, as you are led by a trained historian tour guide through these famous sites. Learn where Chicago's history still whispers after dark!
Check Availability✓ Expert Tour Guide
✓ Go Inside Famous Hotels
✕ Tips and Gratuities for Tour Guide
15 min
Our expert host will meet you at the starting point and begin to explain the architecture and haunted history along the Chicago River.
15 min
You will see historic buildings that operated as speakeasy bars of the Prohibition Era, and see famous spots connected to legendary bank robber John Dillinger.
15 min
Interact with the largest Picasso in the world as you learn about Chicago corruption, and the ghostly hauntings of the Chicago Theater District.
15 min
Go underground and explore the site of a famous 1920s gangster 'whack.' Learn about the exciting height of Prohibition gangster history, right where it happened.
15 min
Learn about the ghosts of the Art Institute, haunted hotels, and more paranormal activity around Chicago's biggest landmarks.
15 min
The tour ends a 5 minute walk from the start. Your host will end with incredible true crime stories, additional recommendations around Chicago, and will assist you with anything else you may need after your experience.
We meet in front of Chase Bank at the corner of State Street and Wacker Drive.
End Point
We end at 78 E. Washington Street, a 5 minute walk from the start of the tour.