Is this real? How will they control this?

Wow. 9% actually seems pretty high for such a ubiquitous service in the 3rd largest city in America. That's a lot of money to be made. A 1 to 5% tax would have been more reasonable.

I don't understand how they enforce this in a localized population. Piracy will probably increase exponentially in Chicago.

In the UK all services are taxed anyway, you know under VAT. Does the US not work this way? The service providers pay this.

We pay 15% tax on these sort of things. Why exactly is this news?

It varies by state most states have sales taxes that are anywhere between 5 and 9 percent on most items but not all most foods don't have sales taxes (exept all foods bought in restaurants have sales taxes added).  There are five states that don't have sales taxes on anything Alaska, Delaware, Montana, New Hampshire and Oregon.

Better than the 13% we have to pay in Ontario.

is that a further 9% than your VAT in the region? or were such things untaxed before?

Shhh, it used to be 15% 

We don't have VAT.  Each state has sales tax, which they control.  That's why for a very long time, there was little or no tax on internet services or even sales, because states couldn't decide or agree how to go about taxing something that was sent in from another state or country.  Slowly, though, politicians came to understand how much money was escaping their clutches and all the states started taxing internet purchases one after another, as best they could.

Sometimes there are benefits to having old men who don't understand technology making the decisions.  Many of us dodged taxes for quite a lot time.  I remember when I could buy anything off Amazon tax-free, as long as it was shipped from out of state.  That was awesome but I certainly can see how it was bad for local economy.

What makes this bad, though, is that it's a city laying down a substantial tax on top of any other jurisdiction.  That can potentially add up to a lot of money if everyone is trying to dip their fingers into the pie.

It really wasn't a good time for me to move to Chicago. Between this and the recent sales tax increase to 10.25%, which is the highest in the US, it really does suck.