You can live in Streeterville for example, as rayiner alluded to in another post... but what happens when you go out with friends??? What if they want to go someplace in say... Wrigleyville... some night??? You're walking back to your car, or trying to get a taxi back to the loop, and you cross too close in front of a police officer, or his vehicle. (Basically, the same thing that bbarn was talking about in his post.) Even though it's completely inadvertent, and done with no ill intent, I've seen this very thing go decidedly bad for people in the past. It seems that it didn't go too well for bbarn either.
So if you're asking for guarantees... I think that reasonable people will concede that there are none.
The best advice is to be aware of your surroundings, and be aware that police are extremely dangerous and best avoided. Just do the common sense kind of things... allow police the path if you see them walking on the sidewalk. Don't look directly at an officer. When approached by a police officer, be extremely deferential. And for goodness sake, if you see police abusing power don't try to intercede. Don't let them see you recording or videoing the incident. When you have an opportunity later... just write an anonymous letter to a newspaper with the video or something. Etc etc etc.
Also... not trying to be even more of a dark cloud here, but I think a word of warning is appropriate on this particular point... if you are black and male, and assuming you are professional as you are a hacker news reader... I'm not entirely certain any of this will work for you in any case.