GeistSR: All you can do is shuffle them around a bit and try again. If it bothers you too much, you can try a smaller group.
8BitDan: I spent an entire day (or at least game day) with zero success. By "smaller group" I assume you mean dismiss a member or two?
Yes, dismiss a member, and the pathfinding is easier.
I find that if you wait long enough, the characters will eventually find a chair. The issue is that, back in the day, pathfinding was extremely primitive. I think what happened is that you double-click on a chair, the game assigns each character to a chair, and they all walk the shortest path to that chair. But if another character gets in their way, they stop, have a brain fart, have to recalculate a path, and then walk again. That can happen several times before they find their chair. If it happens too many times, their brain fart completely takes over and they just stop walking. At which point you want to double-click on a chair again and restart the process.
If you have less people in your party, you have lower chances at having a collision.
This can be very annoying if an NPC happens to walk over your carriage or magic carpet. That may sometimes result in a situation where your characters can't sit down b/c that NPC is in their way, and you can't really use the vehicle until you rest for a number of hours and the NPC goes to another location (e.g., to bed).
It's an old game, with old technology and old algorithms. This is why playing with newer Engines, like Exult, can help to bypass these bugs. Of course, Exult comes with its own bugs, but they are less numerous than the original game. =P