Going to Chicago itself doesn't bother. Been there 100's of times. As long as you don't sell drugs and get yourself caught up in a bad relationship you are generally ok in life.
Walk the lakeshore, go to the navy pier. Southside Chicago is a lot more rougher but as long as you stay to yourself and don't do stupid things the probability of you randomly getting shot is slim. Just don't flash a wad of cash.
To me I will probably never attend a draft because when it comes to the draft I want my own time, I don't want to watch it with 100's of morons who booo or think their pick is great when they barely know the player being selected. It's hard enough to go to a game and bite your lip at stupid fans.
They say that love is more important than money, but have you ever tried to pay your bills with a hug?