I agree with @Matthew Olszak. The overall migration of millenials to cities is going to keep Chicago growing, even if baby boomers and the middle aged start moving out. Businesses are still coming back to the city, Motorola being the biggest one off the top of my head, and jobs are still plentiful. I personally moved to Little Village to get started in real estate because the prices were low and I could handle the crime and quality of life here (tons of amazing Mexican food helps too).
I think Garfield Park is going to be an area that actually sees some decent growth, but the crime rate in the neighborhood is going to slow that down for a while. That said, I'm looking at possibly expanding into North Lawndale just south of there hoping that the Pilsen gentrification keeps moving west. I think GP is going to see the same thing eventually, but it's going to move out from the West Loop, so the area near the conservatory will take a bit to see it.