One of the things recommended to me by numerous people was the Gangster Tour of Chicago run by these folks over here. As far as tours go, it’s a pretty easy one. You take off in a big black bus and two people (dressed in character) give you the low down of the history of the city with that special gangster point of view.

Unfortunately the bus itself, reminiscent of an old American-style school bus wasn’t particularly great for taking photos and let me focus more on the story that unwound itself. We visited many sites around Chicago, places where many of the gangsters grew up, where the battles were had, why turf wars started (and ended) and lots of little detail that would be easy to miss simply walking by.

The tour covers a lot of greater chicago as well so is a great way to see parts of the city that you wouldn’t think of really visiting including a drive by through Chicago’s tiny Chinatown and probably just as sizeable Little Italy neighbourhoods. Some of it gets pretty cheesy at times but was still well worth the US$28.