John Calvin Commentary Isaiah 37:22

"this is the word which Jehovah hath spoken concerning him: The virgin daughter of Zion hath despised thee and laughed thee to scorn; the daughter of Jerusalem hath shaken her head at thee." — Isaiah 37:22 (ASV)

The virgin daughter of Zion. There is greater emphasis in this address to the whole Church than if he had said the same thing to Hezekiah as a private individual, for this circumstance heightens the baseness of treating with scorn the defencelessness of a wretched people, as if the aid of heaven had been of no avail. Thus, he censures the blindness of Sennacherib in disregarding God and haughtily despising an afflicted Church.

Cities are frequently called daughters (Psalms 9:14). Sometimes also, as we have formerly seen, delicate cities are called virgins (Isaiah 1:8 and Isaiah 23:12).

But here he intended to express the weakness of the city of Jerusalem, because she was like an orphan and destitute virgin, insulted by this base ruffian and infamous robber; while God, as the father to whom this insult is offered, declares that he knows well what the schemes of that wicked man are, and what the condition of all Judea is.