Downtown in the skyscraper districts during the daytime isn’t all that bad.
Lots of people working downtown live in the suburbs, which are safer at night.
Outwards migration from Chicago due to taxes, regulation. Not as bad as Detroit area but just give it time.
I work in the Sears Tower (well, it’s now known as Willis Tower but no one calls it that), but live 25 miles west in another county. I take the train to and from work.
The Loop in the daytime is okay. The west side of Chicago at any time of day is a war zone, as is much of the south side. The west side neighborhoods of Pilsen and Little Village are not even part of the United States, as they have been wholly annexed by Mexico, and the Mexican flag is prominently displayed throughout those areas.
Chicago anywhere is a dangerous place after dark. Situational awareness is critical. And Illinois now has CCW so at least the law-abiding citizens some sort of chance against the ferals, but the places one can carry in the city are restricted by the respective business owners. Out in the burbs, outside of Cook County, it is a hell of a lot safer, and CCW is quite common.
Libs there just don’t like you fighting back against your attackers though. Tends to reduce their voter base.