Default jetways are known to be very buggy, especially as wheels contacts are concerned and, unfortunately, nobody is going to fix them, since it's a bug that dates back to FSX, and there nothing we can do to prevent it, since it's the sim itself that animates the jetway.
That's why many scenery developers are switching to SODE for jetways, which is what we did for all our recent sceneries.
As you might know, O'Hare is being remade from scratch, and of course will have SODE jetways, so these issues won't happen.