I live 2 blocks from where the main stadium (athletics stadium) would be built in Chicago. They would need to do a fair amount of work to get the area set-up, but I think the problems with the area are way overblown relative to other areas. Despite Charlie’s experiences, I have rarely had issues with traveling (during the Taste of Chicago, I went from where the stadium would be on the south side up north past Skokie and back in <90 minutes each way). Yes, it backs up bumper to bumper during rush hour head towards the city or going north or west from the city in the evening, but that happens in EVERY major city, period.
Crime would be a major concern pretty much everywhere except Tokyo (relatively). I am somewhat disappointed in the south side (of Chicago) not getting an influx of money because it is really economically downtrodden (relative to the rest of the city) and this might have helped it out. Of course, the city would have likely gone into debt as a whole, so who knows whether or not it would actually help in the long run.
Rio being a war zone is putting it lightly…