A rather simple game once you figure out the above. This issue was remedied and then some in the sequel, aptly named Boss of Chicago 2, which is almost impossible to complete on your own. I haven't yet found anyone stupid enough to play it with me, and I don't think I will bother trying any more.
Try it if you like, but Prohibition (Infogrames, 1987) looks better. I might give that a whirl soon.