@Gargamel,
I lived northside, sort of -- Ukrainian Village when it was still filled with bitter grannies and evenings were punctuated by gunshots on from the far side of Western -- but everywhere I worked for any length of time was attached to the city/mob apparatus -- construction corporations that built parking garages in city and big prairie business parks for now-discredited corporations like WorldCom, Chi Public Schools building, **** like that. Upper management were always invisible except for occasional sweeps of the premises with entourage in tow, middle management were all grandchildren of northern or eastern European immigrants and tended to reveal themselves as casual bigots over time, bottom rung were all Southside black folk with the odd white freak or young married Mexican thrown in. I saw the pattern repeated in enough places that I took it to be the norm for the city, and I generally saw these places from the bottom up, with seamy underbelly exposed.
All that said, it was 1998, the city was just coming to grips with widespread gentrification, the Northside project tenants had been kicked out but the buildings hadn't been knocked down and were full of squatters. Roaming gangs with baseball bats patrolled the area between Cabrini Green and the Rush St. bars where young white pricks chomped nauseously on expensive cigars. Chicago was the nation's murder capital that year with a round 600 homicides, there were rumored to be not one but two serial killers working the neighborhoods around UIC, bands of feral dogs were roaming the no-man's land between Little Italy and the United Center. The city utterly failed to clear snow from Southside streets for six weeks following the New Year's Day blizzard, trains were breaking down or running off the track and Metra had 3 fatal accidents, there were shoving matches just to get on the jam-packed buses on Chicago Ave...
It is possible that this was an unfortunate time to form an impression of Chicago.
That said -- I found the parking-spot-claiming lawn furniture bizarre and in keeping with the other negative impressions I was forming of the city ------- but I admit that I may not have fully appreciated its utility, as I took CTA to work (or walked the 20 blocks to the loop, which was faster for the first few weeks after the blizzard) and most of the people in my neighborhood appeared to be retired or unemployed.