We got to Chicago in plenty of time to catch the connecting overnight train.  Our experience in Chicago was the same as it was on the way up: they do not seem to have any kind of functional system for loading passengers on the train.  They do this every single day, but it's still chaos. Normally, they board the first class passengers (those in sleepers) first, and they called us out of the lounge about 30 minutes before the train was due to depart.  When we got down to the gate, however, the train was not there.  Then when the train did finally show up, they decided to board all the coach passengers first.   What the heck?  We ended up standing in the boarding line for more than half an hour. They could certainly have left us in the lounge until they were actually ready for us. The train was about 40 minutes late leaving Chicago--and it originates there.  Bizarre.

We found out much later that there had been a last-minute problem with the sleeper car and they had to swap it out for another one.  This explains why they boarded the coach passengers first--the attendant was no doubt running around madly trying to get the compartments ready. This does not explain why they didn't leave us in the lounge.

We lost about 2 hours overnight to freight trains, so by breakfast time, we already knew we would miss our connection in DC.  The dining car attendant was very helpful, though, in encouraging us to call Amtrak reservations right away, before we got into the mountains where there would be no reception, and we had no trouble changing our reservation to a later train. 

Ultimately, we were about 3 hours late into DC, but had plenty of time to make the new connection.  That train lost yet more time, so we finally got back into Richmond about two and a half hours after we were due, and home about 9:45.  But we did not derail!