Thank you, everyone for your help. By using the Amtrak reservation site, this is what I have come up with:
LCH-NOL ? pay coach, because we have to stay overnight in NOL?
NOL-CHI, CHI-WPT 1 zone bedroom 25,000 points
WPT-WFH pay coach
WFH-PDX, PDX-SAC,SAC-DEN, DEN-CHI, CHI-NOL 2 zones...