I would argue that these answers can be substantiated through Chomsky's essay: Language and Freedom.
Q: [...]whether it would help me better to understand the philosophy of language?
In the first few paragraphs Chomsky writes about "theoretical work", "formal grammatical structure" and "universal grammar". Although he doesn't explicitly write so, it is clear that his work entails the theoretical side of language and not the philosophical. However, he also writes:
The subject is of particular importance. It is appropriate to regard universal grammar as the study of one of the essential faculties of mind. It is, therefore, extremely interesting to discover, as I believe we do, that the principles of universal grammar are rich, abstract, and restrictive, and can be used to construct principled explanations for a variety of phenomena. At the present stage of our understanding, if language is to provide a springboard for the investigation of other problems of human nature, it is these aspects of language to which we will have to turn our attention, for the simple reason that it is only these aspects that are reasonably well understood.
From this we can deduce that he is not participating in the philosophy of language. Rather he is providing tools to do so because his goal is to "construct principled explanations for a variety of phenomena" which includes language.
So, the answer there would be yes. He helps you to better understand (through construct principled explanations [of language]) the philosophy of language.
Q: [...]Also if you have read the Essential Chomsky, is it likewise a good introductory guide to his philosophy on language?
The nature of this question begs a subjective answer, but I would argue no because of the reasons mentioned in the previous answer.
Q: [...]in introductory text that connected Chomsky's views on language with his politics.
Here are three quotes taken from the essay:
In what way are language and freedom to be interconnected?
I would argue that this article is a great starting point. Although "freedom" obviously isn't necessarily connected to politics, it doesn't take Chomsky too long to start intertwining them.
Sophistic politicians and intellectuals search for ways to obscure the fact that the essential and defining property of man is his freedom: “They attribute to men a natural inclination to servitude, without thinking that it is the same for freedom as for innocence and virtue – their value is felt only as long as one enjoys them oneself and the taste for them is lost as soon as one has lost them.”
From there he weaves an argument by using Rousseau’s Discourse on Inequality which he explains further in this video to come to a "connection between language and freedom".
Were we to combine these speculations, we might develop an interesting connection between language and freedom. Language, in its essential properties and the manner of its use, provides the basic criterion for determining that another organism is a being with a human mind and the human capacity for free thought and self-expression, and with the essential human need for freedom from the external constraints of repressive authority. Furthermore, we might try to proceed from the detailed investigation of language and its use to a deeper and more specific understanding of the human mind.
Conclusion
To conclude I think this one essay not only answers both of your questions, but it also functions as a great introduction to Chomsky's views on language and his politics.
