Absolute Kafkaesque urban planning.
The primary reason the parking deal never goes away is that it allows the city to blame "investors" for doing something it was already wants to do (keep lots of street parking).
Ok but as an urban planner it's a whole lot easier to tell your boss "hey we're removing 5 parking, spaces we'll lose x dollars per year in parking fees" than it is to say "hey we're removing 5 parking spaces and we need to come up with $5 million to pay the parking company"
Or broken windows at the company' C level suites houses?
The "answer" here is either to suck it up (which will happen) or, if you allow room for it, it starts with little acts of violence and ends with effective change or full blown riots
Just to clarify - I'm not advocating for anything like that. I'm just saying - try to picture the people from Paris in this situation and tell me what would happen (and if the contract would stand)
The courts absolutely fold versus popular pressure
This makes complete sense though. The company and the city signed a deal for X amount of meters for Y amount of years. That no doubt went into the financial planning for Profit/Loss. If the city were to remove meters they would be breaking the contract as there are no longer X meters and that much less revenue that the company paid upfront for.
Why? Is "parking" limited to cars? The city can apply the meters to bicycle/scooter/ebike/skateboard parking. Once upon a time many bicycles were regulated and some even required license plates. Chicago seems free to switch people other modes of transport and simply continue the parking fee system accordingly.