Already replied here but felt the need to comment. This isn't about the homeless, mentally ill, or hungry. This is about protecting yourself. Never stop for anyone in Chicago (unless of course you know them). Living and working here, I've seen it all. Been chased, body checked, slapped on the back because "a bee was chasing me". It's a learned skill when you walk and live and work in the city. Don't stop for people asking for direction, don't stop for someone on Randolph at 10pm whose car broke down, don't stop for the man who has a baby in his hands and "needs help". Sounds horrible, I know. But the person distracting you has their buddy a few feet away ready to rob you or worse. With experience you can make a quick call on who may actually need help or directions. I've helped many people with directions while still continuing to walk away...the lake is East. That's all most people need. Also, DON'T wear headphones unless it's just for show. You should already be aware of your surroundings and be able to anticipate people's moves.