The city installed red light cameras, and there is a bribery scandal going on regarding that deal. The city leased the parking meters for a billion dollars, but the contract is almost an object lesson in what not to do as a city. Rates for parking more than doubled, and now Chicago has the highest parking rates in the nation. The city is forced to pay whenever a spot is unavailable or is removed, for the entire duration it is unavailable. If the city wants to put in a bike lane, they have to pay something like $26k per parking spot vacated. If they want to close a street for a festival, they have to pay as if the parking spots were at 100% occupancy for the entire duration of the festival. The city gave up a massive amount of city planning ability as a result of that deal. [3] (added as an edit)
Furthermore, both Illinois and Chicago failed to pay into the pension plans they have promised their workers, leading to a massive budget crisis. Chicago and Illinois are basically forced to pay for pensions as they come up rather than paying with money that had been gaining interest over the length of the employees tenure. On top of that, Illinois is one of the few states that do not tax retirement income, compounding the problem. (Which makes sense, cause retirees vote, but I digress)
On top of that, Chicago has the third-highest number of police per-capita in the nation, after Baltimore and Washington DC. Our police have routinely been caught lying under oath. Our former States Attorney, Anita Alverez, (who is actually the mother of a friend, unfortunately) was a joke, who refused to charge police officers for lying under oath. She otherwise took a tough-on-crime policy, and pursued harsh sentences and supported the policies that basically set the police at odds with minority communities in the city. She would bend over backwards to defend convictions that had been overturned, once suggesting that a man cleared of rape may have been engaging in necrophilia. Policies like these led to Chicago being titled "The False Confession Capital"[2].
And while you could probably hide as many people in Chicago as in LA, the transit situation would be a nightmare, because all transit is centered around being able to go to the loop. So you'd have everyone trying to go through the same area, unlike the more distributed system that exists in LA.
All of this is a real shame. Chicago is a great city, one which I'd sincerely like to share with the world. The centerpiece of the Olympics would have been in an area of the city that is undervalued and under-visited. The plan also did a great job of spreading the competitions around and using the existing infrastructure. For instance, the kayaking competition was going to be held 90 miles away in South Bend Indiana, where a whitewater kayaking course already exists.
[1] “If [Illinois] isn’t the most corrupt state in the United States,” he said, “it is certainly one hell of a competitor.”
http://www.chicagomag.com/Chicago-Magazine/December-2010/Why...
[2] From 60 Minutes - Alverez suggest necrophilia as a possible reason who
http://www.cbsnews.com/video/watch/?id=50136707n
[3] http://www.chicagoreader.com/Bleader/archives/2015/02/19/may...
