I managed to miss my bus back home, so I got plenty of time to think about life in Chicago. Safety isn't really too much of an issue, but I swear there are like ten thousand homeless people that try to beg some money off of you. So, without further ado, a bit of advice (mostly common sense) to avoid the panhandlers.
1. Don't look like a tourist.
If you must carry stuff around with you, avoid luggage if at all possible. A single backpack or briefcase/messenger bag is no big deal. Also, look at a map before you get there if you have a specific destination in mind.
2. Don't be a total jackass.
If you are going to be travelling both alone and late at night, don't dress in exorbitant clothing or jewelry.
3. Always look in a hurry. Failing that, look pissed off.
If you cannot avoid looking like a target for the panhandlers, put on your most "I'm behind, don't mess with me" face. I have mastered what I will call the 'crazy-pissed white boy' look. It either says a)mess with me and die or b)I have nothing of value. I'm not sure, which, but it really doesn't matter.
--Just a few more words on the panhandlers (beggars)--
Some of them will ask for your money outright. Others will offer to hail a taxi for you (rofl) or give you directions in exchange for some money. Shoe cleaning services are also 'offered' in this way.
The most subtle and clever panhandler I met was still quite stupid. Here's the story...
I was coming out of Union Station to wait for my bus to arrive, and on my way out the door, some random guy (with a stuffed duffel bag and wallet/checkbook thingy/passport booklet in his hands) made a comment about 'getting the runaround in this place.' I said nothing, and sat down outside to wait. He proceeded to sit down next to me and tell me some sob story about how 'Amtrak screwed up and wants to give me a voucher and you know what vouchers are it means they are good at a later time but I gotta get there tomorrow but I don't have enought money because I already paid for the ticket once but they gave me a voucher...'[blah, blah, blah, etc. The lack of punctuation was me stressing the rambling nature of his speech.]
After this had gone on for a while, he eventually moved on to how 'I ain't even that much short of a ticket but I gotta get there tomorrow because my sister broke her leg.' Even if you are a total dumbass with absolutely no sense of intuition, at this point there should be no way you should think the guy is telling the truth. No one gives a shit if they show up a day late for a broken leg. I decided to humor him and see how gullible/stupid he thought I was. After I played along for a bit (this was the first time I responded to anything he had said) I convinced him to tell me how much he needed. This is what he said, verbatim: 'I ain't even that much short, just two hundred dollars.' So I made some comment to the effect of "Oh, that's too bad, but I just gave my last $200 to the beggar before you." He shot me a dirty look and got up. I heard him mutter under his breath 'How the fuck did he know?'
All in all, that situation was hil-freakin-arious.
He wouldn't recognize subtlety if it hit him over the head.