Assessing reachability for a dynamical system, that is deciding whether a certain state is reachable from a given initial state within a given cost threshold, is a central concept in controls, robotics, and optimization. Direct approaches to assess reachability involve the solution to a two-point boundary value problem (2PBVP) between a pair of states. Alternative, indirect approaches involve the characterization of reachable sets as level sets of the value function of an appropriate optimal control problem. Both methods solve the problem accurately, but are computationally intensive and do no appear amenable to real-time implementation for all but the simplest cases. In this work, we leverage machine learning techniques to devise querybased algorithms for the approximate, yet real-time solution of the reachability problem. Specifically, we show that with a training set of pre-solved 2PBVP problems, one can accurately classify the cost-reachable sets of a differentially-constrained system using either (1) locally-weighted linear regression or (2) support vector machines. This novel, query-based approach is demonstrated on two systems: the Dubins car and a deepspace spacecraft. Classification errors on the order of 10% (and often significantly less) are achieved with average execution times on the order of milliseconds, representing 4 orders-ofmagnitude improvement over exact methods. The proposed algorithms could find application in a variety of time-critical robotic applications, where the driving factor is computation time rather than optimality. the