The days of Al Capone are long gone, but Chicago’s notorious past is still good for business, it seems, given the popularity of these “Gangster Tours.” The 2-hour bus trip takes you to all of the city’s old hoodlum hangouts from the Prohibition era, including O’Bannion’s flower shop and the site of the St. Valentine’s Day massacre. The focus is definitely more on entertainment than history (guides with names such as “Al Dente” and “Ice Pick” appear in costume and role-play their way through the tour). It has its cheesy moments, for sure, but the trip does give you a pretty thorough overview of the city and its mobster ties.