Yes, Netflix chooses to serve Chicagoans, and if they’d prefer not to, they can. There have been a few “make the customers angry, so they write to their representatives” attempts throughout history, but I doubt a 99 cent tax for Netflix is enough to risk it.
As a related thing, look at Spotify vs Apple on the App Store. That 30% is material.
But I don't think this is actually possible in the EU in the long term. They want to do away with companies only serving digital services to some EU member states, but legislation still applies per country. What if the rest of the world decides that this stuff is great for taxation as well? Then you won't be dealing with the tax code of an American city, you'll be dealing with the tax code of a city in some small country.
As a related thing, look at Spotify vs Apple on the App Store. That 30% is material.