St. Charles Air Line Bridge, Chicago, Illinois, USA

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Chicago’s troubled past—violent mob-related murders, fatal disasters on a grand scale, and chilling cold cases—makes for restless spirits. But what makes ghosts speak "especially loudly here,” says Ursula Bielski, owner of the Chicago Hauntings tour company, is the city's history of covering up the tragedies. In a grassy area on North Clark Street, you might hear barking, when there is no dog in sight: Believers say that it’s Highball, the German Shepherd that was tied to a post while his owner was executed with a machine gun, along with six other rivals of infamous Chicago crime boss Al Capone. Ghosts are said to haunt Death Alley behind the Oriental Theater, formerly the Iroquois Theater, where almost 150 plunged to their death as a fire broke out; hundreds more perished inside. Even Oprah, apparently, is not off-limits: A “Gray Lady” allegedly drifts about her Harpo Studio, which, back in 1915, was an armory where 844 victims of the Eastland Disaster lay dead, waiting for loved ones to identify them. (Their ship, heading for a company picnic, suddenly rolled over while tied to a dock on the Chicago River.) Perhaps the most spine-tingling is the tale of Resurrection Mary, who was killed by a hit-and-run car, after leaving Willowbrook Ballroom on Archer Avenue. Drivers have reported picking up a young, dazed, blond woman in a white dress, asking to be dropped off near Resurrection Cemetery—only to have her vanish into thin air upon arrival.