How's the internet service in Chicago these days? Is it AT&T? If not, who's running the show?
AT&T, Xfinity, RCN, etc are all here, competing with each other. If you live in a dense part of the city, you've got half a dozen other providers to choose from as well. Google-owned WebPass can put a microwave dish on your roof and offer 100+ mb/sec for $50 or less per apartment. Mine is a local company that runs a huge fiber line direct from the nearest exchange center and puts a managed switch in the basement, with each unit having a cat5 line direct to the switch. It's $25 per month for 250 mb/sec symmetrical with direct peering to Amazon, Netflix, Apple, and a few others, and all the common areas like the pool deck and gym have free wifi running at those speeds. I can upgrade to gigabit for an extra $25 per month, which I did for the first few year. But it works so well that I don't bother anymore.
The current subsidized low income internet package is something like $10-15 per month for Xfinity and it's 10-20 mb/sec.
The issue is not rich vs. poor. My internet is cheap because our building has contractually guaranteed a single monthly payment on behalf of the many units in the building for some number of years. You can make an investment based on that.
The City of Chicago is contractually guaranteeing payment on behalf of an even larger number of people. Any private company can make an investment in better infrastructure based on that. But the City is content with letting Xfinity provide garbage service in exchange for that money. If they City said "we will guarantee payment of up to $15 per month to any entity that can provide gigabit service to low-income families" there would be multiple bids from local companies, and they'd all be able to do it profitably.
Also because the economics of making your building a live, on-net premises are much more favorable for the ISP. Their capex to make your building live is based on a calculation for the expected number of units that will sign up in years 1, 2, 3, 4, 5 and the revenue projections. In the telecom industry this is an "MDU" - multiple dwelling unit.
The cost per unit served in a 65 or 95 unit apartment/condo building is much more favorable as compared to building a new GPON FTTH network (even when 100% aerial on poles) to every house in a neighborhood of individual wood frame houses.
You mentioned Webpass above. Where Webpass got started, in the SF bay area, they did precisely what I described above because they could make the economics work by focusing exclusively on MDUs.
You almost always can get both RCN and Xfinity--and they compete pretty hard. AT&T is always available, but its shitty DSL. Supposedly some parts of the city have fiber, but I'm 0/3 at my locations.
I'm paying like $50 + tax for 500 mbit down / 20ish up. I'd trade that for 100 mbit symmetrical, but that's not happened on cable anytime soon.
I bet like 20% of houses at most are networked well enough to even use 200 mbit.
Signed- lucky person who pays $57 for symmetric gigabit in west town.
Many years ago, people got really tired of companies digging up roads, putting in utilities and then repaving the road, only to have some other company come in and dig up the road again a few weeks later. So the city now has an ordinance - if you are going to dig up the road, there has to be an advance public notice, and anyone can lay utilities once you are done but before you've repaved. And once you've repaved, there is some time limit before anyone is allowed to dig up the road again. This makes it pretty cheap to lay dark fiber that will someday get lit up, and now Chicago is reaping the benefits.
These small local ISPs are super efficient - they concentrate on infrastructure and support, with 1 or 2 people for sales and billing: one sale equals hundreds of customers, and hundreds of customers equals a single payment.