a lot of robot vacuums have problems with bases like that (bar stools, etc).
one way of dealing with it is to raise the chair just enough that the bumper sensor hits it and retreats instead of trying to climb it.
you could attach something like this to the bottom:
https://www.amazon.com/Woodpeckers-24-Wooden-Circle/dp/B00W20BHIK
mock it up first with magazines or something to figure out how high it has to be to make the robot reverse when it hits it