Your guess regarding the canonical projection $\pi \colon K^* \to K^* / {K^*}^2$ is correct, there is an infinite subset of primes in $\mathbb{N}$ whose image under $\pi$ is also infinite.
Let $\mathbb{P}$ be the set of primes in $\mathbb{N}$. For any $p,q \in \mathbb{P}$, we have that
$$
p{K^*}^2 = q{K^*}^2 \iff \sqrt{p/q} \in K^*. \tag{1}
$$
So, let $S := \{ p/q \in \mathbb{Q} : p,q \in \mathbb{P}, \sqrt{p/q} \in K^*\}$, and $\sqrt{S} := \{ \sqrt{r} : r \in S \}$. Consider the intermediate field $L := \mathbb{Q}(\sqrt{S})$.
Claim: If $\lvert S \rvert = \infty$, then $[L : \mathbb{Q}] = \infty$.
Proof. Suppose that $\lvert S \rvert = \infty$. We show that if $Y = \{ p_1/q_1, \dotsc, p_N/q_N \} \subseteq S$ and $p/q \in S$ is an element such that $p \not\in X := \{p_1,\dotsc,p_N,q_1,\dotsc,q_N\}$, then
$[\mathbb{Q}(\sqrt{Y})(\sqrt{p/q}):\mathbb{Q}(\sqrt{Y})] = 2$.
So, suppose for the sake of contradiction that $\sqrt{p/q} \in \mathbb{Q}(\sqrt{Y})$. Then, $\sqrt{p} \in \mathbb{Q}(\sqrt{X},\sqrt{q})$. But, $p \not\in X \cup \{ q\}$, so $[\mathbb{Q}(\sqrt{X}, \sqrt{q})(\sqrt{p}):\mathbb{Q}(\sqrt{X}, \sqrt{q})] = 2$, by the result here. In particular, $\sqrt{p} \not\in \mathbb{Q}(\sqrt{X}, \sqrt{q})$, a contradiction.
Now, we show that there exists a sequence $(p_i/q_i)_{i \in \mathbb{N}}$ in $S$ such that $p_{N+1} \not\in \{ p_1,\dotsc,p_N,q_1,\dotsc,q_N \}$ for each $N \in \mathbb{N}$. This can be done by induction, and using the hypothesis that $\lvert S \rvert = \infty$.
Pick $p_1/q_1 \in S$ arbitrarily. Assume that $p_1/q_1,\dotsc,p_N/q_N$ have been chosen for some $N \geq 1$. Since $$\{ p_1,\dotsc,p_N,q_1,\dotsc,q_N \}\tag{2}$$ is a finite set of primes, and $S$ is infinite, there must exist a prime that "occurs" in some element of $S$ that is distinct from the ones in the displayed set. Since $p/q \in S \iff q/p \in S$, we can choose an element $p/q \in S$ as required.
Hence, $[L:\mathbb{Q}] = \infty$, because for every $n \in \mathbb{N}$, there is an intermediate field $L_n := \mathbb{Q}(\sqrt{p_1/q_1},\dotsc,\sqrt{p_n/q_n})$ such that $[L_n : \mathbb{Q}] = 2^n$. $\blacksquare$
Thus, if $\lvert S \rvert = \infty$, then $[L : \mathbb{Q}] = \infty$, so $[K : \mathbb{Q}] = \infty$, which contradicts that $K$ is a number field.
Hence, $S$ is a finite set. In other words, only finitely many of the cosets $p{K^*}^2$ collapse onto each other. There remain infinitely many distinct cosets of the form $p{K^*}^2$ for $p \in \mathbb{P}$. Hence, $K^*/{K^*}^2$ is infinite.