When I worked in downtown Minneapolis, I'd get off the bus just as we entered downtown and foot it the rest of the way in, usually through the skywalk system.I haven't been to Chicago in ten years or more, but the "panhandlers" there were aggressive. I don't carry cash, and told a guy that in Chicago, and he got up in my face and called me a liar -- along with a tirade of profanity. Thing is, I really didn't have any cash to give him.
We had our regulars for beggars there, same places every day, and they got to be as familiar as the shop workers and shoe-shine guys.
One guy was known to be fairly aggressive, he'd shout to you specifically as you'd walk by, "Hey! You! Yeah, you with the camera bag! I see you! You better get your butt over here! Don't keep walking! You'll be sorry later!" - that sort of thing, and nobody really took him too seriously.
One guy, probably from outside the city, did stop to toss some pocket change in his bucket, and the beggar started screaming at him, "Change?! CHANGE?! What the am I supposed to do with change, ! You better get that outta my bucket and find some bills, you !"
The guy was terrified and sort stuck in place, until another commuter just kind of swooped in and rescued him.