Chicago Haunted History and Gangster Tour

Fell the tug of history and dive into the breathtaking events of the past. On this intriguing and unusual tour, you will explore another side of famous locations and get acquainted with haunted places filled with a spirit of gangsters and speakeasies of the roaring 20s.
Hear the captivating stories of Chicago’s past and feel the curiosity level rising as you immerse yourself into those times.

Discover the dark and mysterious history of the Chicago downtown
Be entertained by the expert local guide who knows the true history of the city
Get to know what lies beyond the famous Chicago facades and what is hidden from the mainstream tours
Visit the most impressive and exciting sites.

Meeting Point

71 E Wacker Dr

71 E Wacker Dr, Chicago, IL 60601, USA

Meet the guide under the "Hoyt's" sign in front of Hoyt's Restaurant at The Wyndham Grand Riverfront Hotel

What's included:

• All fees and taxes
• Ghost stories and spooky haunted sites
• Iconic views of Chicago
• Tales behind Chicago’s gangster past
• Historian local guide with expert knowledge

Not included:

• Gratuities

What to expect:

Duration: 2 hours

Downtown / The Loop

Chicago, Illinois

Explore the famous neighborhood from a different perspective. Get to know the gangster tales and listen to the facts about the infamous crimes, which took place there. Follow the traces of Al Capone and other criminals who operated during the 1920s-1930s. Learn everything about Chicago underground as you wander around the district.

50 minutes

Millennium Park

Chicago, Illinois

Visit Millennium Park, one of the principal attractions of Chicago with a lot of landmarks and fascinating art objects, including the famous Cloud Gate. Learn some surprising facts about the place and its history.

15 minutes

Palmer House Hilton Historic Lobby

17 E Monroe St, Chicago, 60603-5608, Illinois

Get inside the oldest hotel in the Windy City. Its history won’t leave anyone indifferent. Hear the tales and legends of the place as you admire its interiors and get ready to see some ghosts since it is considered to be haunted.

15 minutes

Chicago Riverwalk

22 E Wacker Dr, Chicago, 60601, Illinois

Stroll along the Riverwalk, listening to the vivid tales of your history guide. Imagine yourself traveling to the past, walking among the buildings which remember those events. Feel the atmosphere and be comforted by your safe and interesting adventure.

15 minutes

Cloud Gate

201 E. Randolph St., Millenium Park, Chicago, 60602, Illinois

Take some pictures with “the Bean”, an iconic landmark situated in Millennium Park. Marvel at the Chicago cityscape reflections

Pass by without stopping

The Chicago Theatre

175 N State St, , Chicago, 60601-3623, Illinois

Discover the legendary Chicago Theatre and its splendid marquee, which is considered an unofficial emblem of the city. You may recognize it from different movies, artworks, and images.

10 minutes

The Congress Plaza Hotel & Convention Center

520 S Michigan Ave, Chicago, IL 60605, USA

Finish your itinerary at the Congress Plaza Hotel, which is thought to the most haunted site in the whole state. Al Capone himself was reported to be seen here many times on the 8th floor. Get inside and maybe you will have a chance to see him with your own eyes.

10 minutes