I've lived in Philly and Chicago and Philly to me is about 1,000 times scarier. Chicago certainly has its scary neighborhoods but you truly have to be looking for trouble to stumble into them. In Philly, you can drive from Villanova and forget to make a turn on your way to the Schulylkill and you think you're going to die. You won't ever miss that turn again. It can go from million dollar mansions to one of the scariest places in the city in about 1/2 mile. Also, most of Chicago is clean. Philly is always so dirty.
IMO Chicago was filthier. I stayed in a "nice section" of the city, but I thought Philly was nicer. Of course, that was almost 20 years ago. Maybe it's nicer there now.
Chicago's downtown is the greatest place...but you wonder off a few miles from downtown as tourists tend to do...and you're asking for trouble...
1. Elizabeth, NJ
2. Newark, NJ
3. Baltimore
4. Washington, D.C.
All four are hopeless Quagmires, and we need to cut and run immediately. If the taxpayers simply stopped financing criminals through taxation, it would remove the welfare safety net. The cities would implode and cease to exist in 30 days; like an accelerated Lord of the Flies.