We consider Hessenberg varieties in the flag variety of $GL_n(\mathbb{C})$ with the property that the corresponding Hessenberg function defines an ad-nilpotent ideal. Each such Hessenberg variety is contained in a Springer fiber. We extend a theorem of Tymoczko to this setting, showing that these varieties have an affine paving obtained by intersecting with Schubert cells. Our method of proof constructs an an affine paving for each Springer fiber that restricts to an affine paving of the Hessenberg variety. We use the combinatorial properties of this paving to prove that Hessenberg varieties of this kind are connected.