I have several friends who’ve moved into Chicago the last few years for various reasons. More active nightlife, but also being able to take public transit, walkable neighborhoods, etc. One of the three left his car at home with his parents in the suburbs, but the other two sold their cars. After several years in the city they are now all getting out ASAP.
All three (guys in their 30s) have been victims of crime on the CTA, either on the L trains or platforms. Phones and wallets taken. These attacks were all during morning/evrning commutes, not late at night.
Two of the three have been victims of robberies while walking home from the grocery store, in broad daylight on a weekend day.
Two lived on the north side, one in the south loop.
Even the close in old suburbs of Evanston and Oak Park (which has tons of Frank Lloyd Wright houses) are crime ridden.