I wouldn't expect it to get any better anytime soon.
My cousin married a guy whose family has lived in Chicago since 1892, with the guy's family having worked for Marshall Fields. With two kids now though and the continual uptick in violence, the whole family sold their 100 year old house relocated to Nashville. My cousin works as a educational psychologist and when her car was hit by stray gunfire in 2010, it was time to go according to her.
Last time in 2006 I was in the Windy City, I stayed at a Marriott right off Michigan Ave across from the park. The hotel lobby that night was riddled with automatic gunfire. Needless to say when I saw the SWAT team repelling down the building next door, I knew it would be my last time there for some time.