Absolutely Chicago Segway Tours

The Ghosts and Gangsters tour offers a fun way to explore Chicago while connecting with its history.

With infamous denizens like Al Capone and historic tragedies like the 1903 Iroquois Theater fire in which more than 600 people perished, it is little wonder that Chicago has its fair share of ghost stories. 

For those who are motivated by the thrill of the haunt and adventurous enough to steer a Segway two-wheeled personal transporter, Absolutely Chicago Segway Tours’ Chicago Haunted Tour — Ghosts and Gangsters offers a fun way to explore the city while connecting with its history.

Led by a certified Segway guide, the tour begins with an orientation on how to use the two-wheel, self-balancing transporters (you get the hang of it quickly) and then it is time to wheel on into the night. 

The Chicago River with its dark waters reflecting the colorful city lights belies a horror that occurred on it more than a century ago. That is when 2,763 Western Electric Co. workers and their families, as well as crew members, crowded aboard the Eastland for an excursion. 

But the boat flipped upside down while still tied to the dock, and 800 people died in the accident. First-person accounts from that day recall the screams for help and waters filled with struggling passengers. Visiting the site at night, you almost can’t help but listen for these whispers from the past. 

At Chicago’s majestic Buckingham Fountain, learn about Al Capone’s yacht and the famous gangster’s legendary criminal deeds, including being the suspected mastermind of the St. Valentine’s Day Massacre where seven members associated with Bugs Moran’s gang were murdered. 

Other highlights of the tour include a glide down the Alley of Death, which held the 600 bodies from the Iroquois Theater fire, and past the site of Fort Dearborn, where Potawatomi Native Americans killed more than 50 soldiers and civilians during the War of 1812. 300 E. Monroe St., Chicago, Illinois 60601, 312/552-5100, chicagosegways.com