In the late 60's I had purchased a nice sportster, XLCH, and, living in an apartment complex and not wanting to leave it parked in the slot parking in front of the building (my place was on a back corner down a corridor with stairs to the second story) I decided to park the bike chained to the stairs. That went okay for a few days till the apartment manager asked that I move it elsewhere. There was a small strip of grass next to the back sidewalk, about 20 feet from my front room window, backed up with a ten foot chain link fence. There was a nice sturdy phone pole right there and that's what I chained the bike to.
One morning I came out to find the bike rearranged a bit and on closer inspection I found a link (case hardend chain) with some hacksaw marks and a few hammer marks on the very sturdy lock. Added a second lock, worked around the one link that was sawn and felt pretty good that it was secure and the perps had given up. I was extra vigilant that night but apparently missed them in the wee hours of the morning but on inspection I found the bike gone and metal splatters and a torch cut chain dangling from the phone pole. Bear in mind, they would have either had to have a portable torch or run approx 75-80 feet of hose back to where the bike was. Guess they really wanted the bike.
Insurance covered it and it was never seen again, likely parted out. So much for Chicago, I moved to Florida shortly after that.