Grew up in Detroit, lived in Chicago for 12 years. People stay out of Detroit for the most part, minus Greek Town, Joe Louis and GM building. So if you don't want to get robbed, raped, murdered, stay out of Detroit.
Chicago, on the other hand, is no longer safe anywhere. We moved out of Chicago because the gang wars started moving out of the gang neighborhoods and into what has always been "safe" neighborhoods. When people started getting shot on Michigan Ave from drive-by shootings, it was time to get the fuck out.
What scared the shit out of me were the packs of kids on their bikes who would randomly pop or literally beat the life out of people for their gang initiations. I'd just about shit myself when I saw groups of kids when my wife was pregnant. Again, this is going on in the nicer neighborhoods (always has, but much worse now)... good kids getting killed while walking home from school, grandmas getting brutally beaten, women constantly getting raped. It's gotten scary bad.
Not to mention Chicago is next to file bankruptcy. They're fucked financially.