Jay Honeck wrote:

Now that I think about it, I suppose we could have asked Flight Watch
to notify Chicago Center when we could no longer hear them, but frankly
it never dawned on me that Chicago really cared that much about what
happened outside of their Class B airspace.

First, Chicago Center doesn't give a crap what happens in the Chicago
Class B.

I've had radar facilities chase me down after I've lost comms with them
during VFR FF. They want to make sure they didn't lose you and
something bad happened to you (like you crashed). Just consider it
an extra service.