Oh yes, it's such a first world problem. Yet, my Roomba has gotten stuck on my Ikea Poang chairs, about once every four or five runs.
The solution I came to was elevating the chair a little bit.
I bought some wooden wheels at Praxis (these are 60mm ones, intended to work as a wheel for, for instance, a storage box, or as helper wheels for a chair).
They are intended to work as wheels, so they are built to have an axle in them. We want to screw them onto out chair, but without the screw sticking out; so, I made sure the screw would recess using a counter sink.
Prepare the chair by pre-drilling some holes. I used a 3mm drill for this. Since the wheels' 60mm is just as wide as the chair's legs, there is no need to measure anything, just use your hand as a guide.
Then, attach the wheels. I used 3.5x20mm screws.
To top it all of, attach some felt protectors. I had some Ikea Praktisk protectors lying around.
There you go! The chair is now just high enough so the Roomba's bumper will hit the chair instead of bravely trying to climb over it. Mind you: this works fine on my hardwood floors, but you may need some additional height if you have carpet.