answer:I have been to Chicago many, many times – most recently last fall. The tourist areas (Magnificent Mile, near the lake, etc.) are perfectly fine and safe and walkable at all hours of the day or night. Same with the University area on the South Side, and the same in the near north and particularly near Wrigley Field. Don’t go to the slums. Don’t go where there is nothing to see. Chicago is a wonderful city – perhaps by 3nd favorite in the US. But don’t go where there’s no need to go. In this way, it’s a lot like New York City – most of it is absolutely fabulous, but parts – particularly low income slums – are not wise. But why would you be going there in the first place?