For three or four years, a homeless man achieved the impossible: He found a free riverfront place to live on pricey Lake Shore Drive. Actually, Richard Dorsay didn't live on Lake Shore Drive, he lived under a bridge over the Chicago River. Unless, of course, the drawbridge had to rise. Then his home was way, way over the Chicago River.
Primary Source
Richard Dorsay was a story I heard about from my Dad, this happened when I was young and he saw it on the news. I asked him for some ridiculous stories about Chicago and one other one. The other one is the Floods that happened in the loop which drained the River into a metric crap ton of underground tunnels that were used for trade in the Industrial Revolution.
The source explains it all but I'll summarize.
He was able to get electricity, stay dry, get a TV Signal, play Playstation from underneath a Lake Shore Drive Bridge with River views.
These bridges are plentiful in Chicago and the city wasn't completely up to par with securing everything. As governments typically are bad at everything.
Chicago still isn't known for law followers and security in some neighborhoods. Source: heyjackass.com
With the flight of capital and people from Chicago due to high taxes and endless clientele fascist dealings with the City and State Governments, it becomes less of a destination for travelling Hobos, but it will always be popular due to it's central location in the USA with many means of public transportation and good food with generous Mid-westerners.
I'll discuss more about my interesting perspectives of Chicago, the North Shore, Suburbs, and it's infrastructure soon.
I grew up in the NW Suburbs and went to Lake Zurich High School where I was indoctrinated into every piece of bullshit the government wanted us to know. Curriculum was trash.
I learned most of what I know about Chicago by working there, living there, and dominating the internet with Linux sysadmin and web surfing.
Thanks for reading,
John