Discover Chicago's Dark and Mysterious Past

Step into the notorious past of Chicago with this Gangsters & Ghosts Guided Walking Tour, combining true crime and paranormal history. Over about two hours, you'll trace the footsteps of infamous criminals, see legendary locations, and uncover secrets that shaped the city during the Prohibition Era and beyond. Led by engaging historians, this walking tour turns stories into vivid experiences, letting you explore the hidden side of Chicago's famous downtown area, The Loop.

Follow the Trails of Notorious Gangsters

The Loop is where history took a dramatic turn under the influence of legendary crime figures like Al Capone and John Dillinger. Your guide will recount events from the roaring 1920s and 1930s, giving insight into how speakeasies, underground tunnels, and illicit deals dominated the streets. Visit sites where major crimes unfolded and gather inside buildings that have stood since gangsters ruled the city.

• Listen to tales of criminal plots and infamous Chicago mobs

• See the secret spots used to evade justice

• Explore buildings that played central roles in the city's underground world

Haunted Landmarks and Ghostly Legends

Beyond gangsters, Chicago harbors tales of ghosts and restless spirits. As you move through the city, your guide will share chilling stories about unexplained occurrences and long-reported haunts. Notable stops include the historic Congress Plaza Hotel, often called one of America’s most haunted hotels, and The Palmer House, where the past lingers in every corridor. Prepare for stories that blend history with the mysterious.

• Tour haunted hotel lobbies and corridors

• Hear renowned local ghost stories

• Uncover why certain sites have a reputation for paranormal activity

A Comfortable, Informative Experience

This family-friendly experience is designed to offer both thrills and fascinating facts without being too intense for younger guests. The walk covers about 1.5 miles with frequent breaks for refreshments and restroom stops. Along the way, your knowledgeable guide ensures the perfect balance of entertainment and historical context, making it ideal for history buffs, true crime fans, and visitors seeking something different.

• All ages welcome

• Opportunities to rest along the route

• Guided by a historian for accuracy and engaging storytelling

See Chicago Differently

Whether you're a first-time visitor or a local, this walking tour offers a unique glimpse into a lesser-seen side of Chicago. It’s a chance to stand in the footsteps of infamous personalities and hear firsthand accounts that make history come alive.

Book your Chicago: Gangsters & Ghosts Guided Walking Tour tickets now!