how hard is it to remove a chair rail?

Ileen Oshell: Cut the caulk ( if it is painted) with knife. Use flat pry bar with a shim under it to keep from damaging drywall . Then fill in nail holes with drywall mud. Then paint.

Clay Lipira: just paint the rail the same color as the wall

Mitsuko Manne: Get yourself a sturdy putty knife. Use it to pry behind the chair rail to create a small gap (eighth inch or less). Once you get a small gap, you can insert a pry bar. Hold the putty knife against the wall behind the pry bar to keep the pry bar from damaging the wall as you pry. Start at one end and work your way down the wall. Sometimes you can just pull it away from the wall once you get started. You will probably have a few small nail holes to repair.