The aim of this article is to link Schubert varieties in the flag manifold with hyperplane arrangements. For a permutation, we construct a certain graphical hyperplane arrangement. We show that the generating function for regions of this arrangement coincides with the Poincaré polynomial of the corresponding Schubert variety if and only if the Schubert variety is smooth. We give an explicit combinatorial formula for the Poincaré polynomial. Our main technical tools are chordal graphs and perfect elimination orderings.