Even outside the loop, I have had nothing but great experiences with your city. I am there pretty frequently - loop, north, south, west. Not to say crime doesn't exist, but I've put myself in positions where I haven't had to deal with it (i.e. haven't joined a gang, don't deal with drugs, keep my wits about me). I may move there down the line. I've found the prices are actually cheaper than Atlanta if you don't mind an up-and-coming neighborhood. I've got a condo saved on Zillow that is under $100k and a short ride on public transit from so much fun.