Fun Routes Via Sleeper Out of Chicago?

Hey everyone! This is my first post here, I’m a long time Amtrak rider and have only been able to ride on 3 long distance routes. I love travel and would love to be able to do more, but most of the common routes I see long distance are either too long to do feasibly without a lot of planning ahead (ie Chicago-Seattle) or like those routes are too pricey.

I’d love to find trips around 9-20 hours in total to fun towns or cities to visit on routes originating or having a stop out of Chicago in a sleeper room that have a chance of not being prohibitively expensive, but I’m still okay paying in the mid or high hundreds, but even with planning on a route nearly a year ahead a lot of them are $1,000-2,000 and that is too unreasonable for me.

Thanks in advance for any help!