Lifelong Chicagoan here. I've never, ever had these issues and all my run-ins with cops have been fairly uneventful, if not pleasant. Chicago cops have better things to do than give traffic tickets usually and the last time I got pulled over (blew through red from a fast yellow) and I was just let go with a warning.

Recently, there is a mentally unstable person in my neighborhood and he decided to sit on my porch and light pieces of paper on fire one day. I called and they were there in 15 minutes and said they could do what they can to help this guy. The cops seemed geniunly concerned about his and my safety. I was floored by how well this call went.

I live in one of the decent, but not wealthy neighborhoods. Chicago is about 1/3rd horrible ghetto and 1/3rd marginal and 1/3rd decent. Life in those other 2/3rd's is very, very different. If you're outside of the typical "northside" neighborhoods the cops are much tougher and much more paranoid about being hurt or killed. I lived in one of those neighborhoods and there's a completely different vibe there. Cops pull up with 3+ squads at every call, take up defensive positions, hands close to weapons, etc. A dog attacked mine when I lived in Humboldt Park and the cops came out and were cool about it, but clearly on edge as I lived in gang territory. In other neighborhoods, I don't see this edge, or the defensive tactices. So yeah, there's something here about cop safety in marginal neighborhoods. I imagine provoking these guys in these neighborhoods leads to bad outcomes.

Also, not to attack the GP, but there is a Chicago cyclist personality I see frequently. They do dick moves with their bikes, cause accidents, never obey any traffic law, scream at pedestrians, have unbelievable senses of entitlements, kick/punch cars, and constantly pretend to be innocent and are often incredibly confrontational when criticized. I can't imagine cops being nice to these people and the GP sounds like one of these people, which may explain many of his experiences. Chicago cyclists have a bad rep for a reason.

That said, I have next to zero fear of the police and lots of fear in regards to the high criminality and massive gang population here. I've been intimidated and threatened on the train multiple times, car/house robbed, had to walk lady friends to their homes/cars many times not out of courtesy but because there was a known rapist loose or the gang kids were clearly looking to start trouble that night, have been uncomfortably close to a gang shooting at least once, hit 3x by DUI drivers, etc. I suspect Chicago cops are tough because Chicago has so much serious crime. This isn't the suburbs.

Wikipedia: Chicago has more gang members than any other city in the United States: 150,000. The city had 532 murders in 2012.

Chicago tribune: Chicago police officers shot 22 people in 2015, eight of them fatally.

532 vs 8, guys. Oh, 150,000 gang members is 5% of the population. That's right, this is a major city where 1 in 20 are gang members.

That said, the powerful Chicago police union is pretty horrible. It exists to protect the worst of the worst, out of some misplaced sense of pride. I would love to see public sector unions eliminated in the city, if not nationwide. They just make things worse for everyone. Society needs an alternative to the union system in the public sector. I find it bothersome that all the recent ant-police sentiment still has not percolated to the police unions. I suspect this is a political thing where liberals can't attack their own institutions. So expect zero real reform.

FWIW, I am darker skinned and do not pass as "white." I'm typically clocked as a Latino. I've always owned older cars , dress very casually outside of work, and live way below my means. I doubt I was treated in any special way because of status/race. I don't fall into the preferred categories.