We actually went to Cuba. There was a window of about a year, maybe two where diplomatic relations loosened. We went as tourists four years ago directly from the US, and I can attest that they live in squalor. The front facing facade of antique cars and colorful tropics gives way to destitute peoples surrounded by hopelessness. We hired a private guide who took us to the not so tourist places. Yes, these are very impoverished people. I’ve never been so uncomfortable, but felt so safe in my life. Uncomfortable because diplomatic relations, though improved, were not good. I always had a nagging feeling that I was being watched. Safe, because tourism is their lifeblood, and attacks on tourists were not tolerated by authorities.
Sounds like Chicago to me.
and a ton of other cities in the US