The problem of a compressed Timoshenko beam of finite length in frictionless and bilateral contact with an elastic half-plane is investigated here. A Chebyshev series solution is found and, for some limiting cases, an analytic form solution is provided. The problem formulation leads to an integro-differential equation which can be transformed into an algebraic system by expanding the rotation of the beam cross sections in series of Chebyshev polynomials. An eigenvalue problem is then obtained, whose solution provides the buckling loads of the beam and, in turn, the corresponding buckling mode shapes. Beams with sharp or smooth edges are considered in detail, founding relevant differences. In particular, it is shown that beams with smooth edges cannot exhibit a rigid-body buckling mode. A limit value of the soil compliance is found for beam with sharp edges, below which an analytic buckling load formula is provided without loss of reliability. Finally, in agreement with the Galin solution for the rigid flat punch on a half-plane, a simple relation between the half-plane elastic modulus and the Winkler soil constant is found. Thus, a straightforward formula predicting the buckling loads of stiff beams resting on compliant substrates is proposed.