Chicago is in the hole for nearly thirty billion dollars. They have been floating the idea of a ten billion dollar bond with the debt structured in a way which lets current politicians escape the fallout from its payment and not having to raise property taxes. The state of Illinois is not well off either with debts estimated at the low of one hundred thirty billion to two hundred fifty billion. An Illinois proposal just to fix state pensions would result in a forty four percent property tax increase for thirty years.
Chicago has a narrower group of people to draw from so besides tourist and sin taxes they have to go after any product consumed by residents of the city and that includes digital.
Why is this all happening, because there is a well hidden largess in government employee payroll and worse in their pension system. Illinois alone is estimated to have over twenty three thousand retirees pulling down one hundred thousand dollars a year or more. A lot of this is from the higher end positions in city and county governments but you can find police and fire there too.
People complain about the disparity in corporate executive level pay to employee should also take a look at the disparity between the same in state and city governments let alone the disparity in retirement to even every day workers in the state. A 100k retirement not counting full benefits is equivalent to nearly forty eight dollars an hour.
So expect more digital taxes in your future.
PS: the Chicago debt is only for pensions, they are down tens of billions more in deferred maintenance and similar debts.