The principle of contextuality is the claim that a word only has a (determinate) meaning in the context of a sentence (in particular: a proposition). This claim can be traced back to Frege and others in the 19th century. (See for instance:
Compositionality: its historic context, T.M.V. Janssen, 2012
Wilhelm Wundt, the neurophysiologist and empirical psychologist (quoted by Janssen) formulated it as:
The real thinking consists of thoughts, and separated from a thought in which it enters a concept has no existence. The same holds for an isolated word in ordinary language when used as a sign for a concept; it has reality only in the context of a sentence. (Wundt, Logik. Eine Untersuchung der Principien der Erkenntnis und der Methoden wissenschafliche Forschung, 1883)
A related, but different, and apparently contradictory claim is the principle of compositionality which is the claim that the meaning of a sentence is composed of the meanings of the individual words. Frege seems to have been dead-set against that because it can threaten "psychologism" (the reduction of mathematics to psychological operations or mere mental "concepts") which seems to make the objectivity and certainty of mathematics inexplicable.
Wittgenstein was strongly influenced by Frege, especially in his early work , but some influence persisted in his later work. The slogan "meaning is use" is a somewhat crude, popularized summary of Wittgenstein's core ideas in the Philosophical Investigations. In Philosophical Investigation 43 he wrote
For a large class of cases of the employment of the word ‘meaning’ —though not for all — this word can be explained in this way: the meaning of a word is its use in the language.
In the Philosophical Investigations this idea is closely connected with his "language games"; it's mainly developed in the context of a pretty far-reaching critique of essentialist (platonist, realist) and psychologist ideas about how words (especially names) and phrases acquire meaning. The critique also implies a thorough repudation of some of his own earlier ideas. For instance in PI 46 he writes:
What lies behind the idea that names really signify simples? (goes on to quote Plato, a quote that ends with) "... For the essence of speech is the composition of names." Both Russell's 'individuals' and my 'objects' (Tractatus Logico-Philosophicus) were such primary elements.
The term "language game" is primarily used in the PI to refer to certain artificial toy "languages" - languages that are much simpler than full-blown everyday language, and that thereby may make it easier to get a handle on the question how meaning is acquired or how meaning can change. Witgenstein uses these "languages games" as a conceptual tool, as thought experiments, to investigate those tricky questions.
The suggestion then is to use game playing as metaphor of how language is generally used (how meaning can be acquired/established/changed/explained/justified).
In the form of a statement you could summarize this as: "Words (or phrases or sentences) acquire meaning by their embedding in social game-like activities."
The way I interpret this is that this is a broader, more general, and vaguer claim than contextualism. The 'ultimate' context for language, you might say, is "forms of life", in other words, certain social customs, behavioral patterns -- but that is an extension of the idea of contextuality. Wittgenstein's "language game" idea can be seen as compatible with both the narrow principle of contextuality and the principle of compositionality.
Wittgenstein's ideas about "meaning as use" and language as family of language games get a more precise, operational, empirical content in computational linguistics. The basic hypothesis (basic for the development of word-embeddings and LLMs) is the distributional hypothesis:
Linguistic items (of whatever kind) with similar (syntagmatic or paradigmatic) probability distributions, have a similar (syntactical) role or (semantic) meaning.
As we've seen, the resulting models have certain peculiar weaknesses, but they are also extremely powerful. The dialogue systems that are built on top of them essentially also parse and generate language in a game-like environment (for instance, there is very strict turn-taking; the human asks a question; the system generates a response). And the rules of the game are - as in Wittgenstein's toy language games - never completely fixed or determined (apart from deep rules that are not accessible to the surface system).
"Meaning" in these systems is in principle totally undetermined. That is,
at any given moment, in actual use, relative to a particular system, relative to particular tasks, it may be determined. But a single word or phrase (or a sequence of letters) can not meaningfully be assigned a "meaning" outside of the system and the tasks that the system is trained on or expected to satisfy. So, like (or even more than) Wittgenstein's language games (and like William James' ideas of language) the implied philosophy of meaning is thoroughly pragmatic. "Context" -- again similar to considering a language game as "context" -- also has a much wider meaning than in the 19th century discussions (it's the context of a large corpus of utterances; both the horizontal/temporal/sequential context and the paradigmatic context; plus the context of different tasks, different modes of deployment, the goals of the community that encounters/uses/produces the system).