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Chicago's Dark Side

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The city’s often-mysterious history offers plenty of material for group exploration, and two top touring companies make it easy for planners to delve into the dark side.

Chicago Hauntings provides completely narrated outings to spooky spots throughout the metropolis that are sure to stir some group goose bumps. From supposedly haunted homes to abandoned graveyards, the tours definitely provide a different take on the city, and even have been rumored to include some actual ghost sightings.

Chicago Crime Tours shines the spotlight on the compelling crime history of the city, taking groups all over town in a comfy climate-controlled bus to investigate crooked characters ranging from Al Capone and John Dillinger to Leopold and Loeb. Stops include the site of the Valentine’s Day Massacre, the most infamous gangland slaying in America’s history.

“Chicago Crime Tours is a fun and interactive experience,” says Lauren Singer, the company’s creative director. “[Participants] escape into Chicago’s criminal past of gangsters and mobsters through hard-hitting facts, entertaining stories, exploration of historic crime scenes and trivia.”

The crime tours can be customized for private groups, themed around topics such as speakeasies, pub crawls and even pizza.

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Zachary Chouteau