Simply Group things – as in the Illustrator command to Group. – Select all the objects for a single month and choose
Object > Group from the menu.
When using the align features, Groups are seen as a single object and will be aligned as such.
So… Group Jan, then group Feb, then Mar, then Apr, etc. You can then choose to align the months, as a whole, to each other.
From your images.. the first image appears as though nothing was technically Grouped (in Illustrator terms).
Here’s a link explaining how Groups work in Illustrator. It May be helpful: https://www.peachpit.com/articles/article.aspx?p=435193&seqNum=4