It all depends on what you intend the $\cdots$ in your expression to mean.
A typical way to define the meaning would be as the limit of the sequence
$$ a, \int_0^a dx, \int_0^{\int_0^a dx}dx, \int_0^{\int_0^{\int_0^a dx}dx}dx,
\int_0^{\int_0^{\int_0^{\int_0^a dx} dx}dx}dx, \ldots $$
Note that in order even to define which sequence we're talking about, we need to decide what to put instead of the not-yet-unfolded part of the "infinite expression" in order to get one of the terms in the sequence -- here I've arbitrarily called it $a$.
And with the way your infinite-stack-of-integrals work, the outcome is that at each finite cut-off the entire stack just collapses into the placeholder you put at the top of it -- so the sequence you're now looking for the limit of is simply
$$ a, a, a, a, a, \ldots $$
This obviously converges -- to $a$ -- so it is not true when you claim that it doesn't. The problem with your infinite expression is not that it fails to converge, but that the choice of $a$ influences what the limit is.
Using limits to give meaning to things with "$\cdots$" in them only works well if either there is a natural "neutral" choice for the placeholder value, or the placeholder value matters less and less the more of the "ideal" infinite expression we include.
The former is the case for the typical case of infinite sums (where it is arguable that $0$ is a natural placeholder); the latter is the case for continued fractions or some cases of infinitely nested radicals.