Not sure I fully understand your question. What points are you actually traveling between? Cleveland and where?
Not all intermediate points on a given run are entered for connections. Every single connecting city pair has to be manually entered in Arrow, it isn't done algorithmically. Not all of them have been, particularly smaller stations.
If Cleveland and wherever along the CZ route don't come up, use the Multi-City option to book Cleveland-Chicago and Chicago-wherever as two segments on one reservation. You want them to be on the same reservation, not separate tickets. That way the guaranteed connection policy is sure to be in place.
The connection is guaranteed between both the Lake Shore Limited and the Capitol Limited and the California Zephyr.