Ultra-reliable communication (URC) is a key enabler for supporting immersive and mission-critical 5G applications. Meeting the strict reliability requirements of these applications is challenging due to the absence of accurate statistical models tailored to URC systems. In this letter, the wireless connectivity over dynamic channels is characterized via statistical learning methods. In particular, model-based and data-driven learning approaches are proposed to estimate the non-blocking connectivity statistics over a set of training samples with no knowledge on the dynamic channel statistics. Using principles of survival analysis, the reliability of wireless connectivity is measured in terms of the probability of channel blocking events. Moreover, the maximum transmission duration for a given reliable non-blocking connectivity is predicted in conjunction with the confidence of the inferred transmission duration. Results show that the accuracy of detecting channel blocking events is higher using the model-based method for low to moderate reliability targets requiring low sample complexity. In contrast, the data-driven method yields a higher detection accuracy for higher reliability targets at the cost of 100× sample complexity.