So I think the part you’re missing is that you’re expecting it to treat a naive date time as if it’s in UTC by default. The whole point of NaiveDateTime is that it has zero timezone information at all. So the first thing you need to do is say “I’m telling you that these digits are a utc timezone date time” then you can go “now convert this to the equivalent time in Chicago”.
Your first attempt was saying “I’m telling you that these digits are Chicago time”.
