We study the synchronization of chaotic units connected through time-delayed fluctuating interactions. Focusing on small-world networks of Bernoulli and Logistic units with a fixed chiral backbone, we compare the synchronization properties of static and fluctuating networks in the regime of large delays. We find that random network switching may enhance the stability of synchronized states. Synchronization appears to be maximally stable when fluctuations are much faster than the time-delay, whereas it disappears for very slow fluctuations. For fluctuation time scales of the order of the time-delay, we report a resynchronizing effect in finite-size networks. Moreover, we observe characteristic oscillations in all regimes, with a periodicity related to the time-delay, as the system approaches or drifts away from the synchronized state.