A couple of years ago, I was arriving at CHI on #6 and we were running about 5 hours late account a boulder-slide in Colorado that messed up the track a bit. They bused (actually, a 30-seater oversize airport van, in my opinion) to IND to meet the Cardinal. We got there about an hour ahead of time, including the 1 hr stop enroute for dinner (on our own) at a cluster of fast-food places at a freeway exit in Illinois. That's the good news...
About a year ago, I was on the Cardinal leaving Chicago exactly on time. We weren't past Roosevelt Rd and in comes a several hours late #4 or #6, I don't recall which. The other one of the two came in about 20 minutes later, according to the Amtrak web site. I felt bad for the connecting passengers. From my perspective, Chicago is more concerned about 'on time' than 'passenger service'. 'On time' is easily measured, 'passenger service', not so easily measured. I stopped flying Continental Airlines 15-16 years ago because of the same problem...not holding a the last plane of the day to my destination for a lousy 15 minutes or so, and they refused to put me up for the night.