And while I'm probably on the same page as you re: Chicago's profligacy, let's face it: Chicago needs to raise money. Economically, aren't consumption taxes better than raising the same money from income or property taxes (or head taxes or corporate taxes)? I'd argue that instituting a city income tax or raising property taxes will move more people out of Chicago than taxing Chicago consumers[1] for internet services.
[1] The effective incidence of sales taxes is complex. But I imagine most Internet services will be able to pass most of the cost onto consumers.