Was very briefly in Chisinau in October for just 24 hours, so my impressions were fleeting. But they were favorable. For perhaps no good reason, I expected a stolid city characterized by Stalinist architecture. While the architecture I saw was truly uninspiring, the city did have a lot of tree-lined streets that made my few walks quite pleasant. And I stayed at a pretty nice smallish hotel (maybe 30-40 rooms?): Hotel VisPas, on a pleasant side street that appeared to be decently located. Nothing really fancy, but pleasant staff that spoke English, a decent room, and a nice outdoor terrace that would have been very pleasant for a meal, drink, or coffee if I'd had time. Also, at least a few of the rooms had balconies.

Of course, this was just a really short visit and I lucked out with some beautiful autumnal weather. My sense is that even in mid-October I was pushing it in terms of getting nice weather, so the window of opportunity for the city, climate-wise, is probably May-September.