A chronological reading plan attempts to order the chapters of the Bible according to when they happened historically. What that means is that you’ll Job showing up in the middle of Genesis-Judges. After that some of the psalms are going to be peppered through the life of David, offering insights into his mental state. The prophets are going to intervene in the accounts of the kings they lived under, rather than all being gathered together at the end of the OT. That makes their motivation all the more vivid.
In the New Testament the Gospels are harmonised, which means there a lot of repetition but you’ll see how the Evangelists told their story differently. When you get to Acts you’ll find the epistle inserted into the moments when they were written. It’ll give you a picture of the history behind this all.
The thing is to remember that for some of this – like the dates of the Psalms and the order of the epistles – there’s a good amount of speculation and historical guesswork.