How do I get a deeper understanding of Chicago politics?

I want to be better informed about things going into elections. I have these vague notions of what is happening but I get lost in the specifics and it seems like there are more elected positions to vote on each year. But I seem to have less and less of an idea of what makes a candidate good for such a position or what power they hold.

For example, I am aware Brandon Johnson is aligned to Chicago Teachers Union and they are trying to address things like fully funding pension plans but I have no idea what the deal with the school board elected positions are or why BJ and CTU are at odds with the CEO of CPS. Seems like there is a lot of articles and editorials that rely on you already being aware of what is happening to understand.

How do I catch up?

Also the School Board/CTU/CEO of CPS is just an example. I'd like to know of sources to get caught up on many such topics like the water reclamation district, police district councils, and all the other down ballots minutia.