re: Train from Nola to Chicago…any opinions?

I did once, in 1979 or early 1980 with my mom and baby sister. Had family in NY, we went from Hammond to Chicago, then took another train to NYC.

I mostly remember that I read Empire Strikes Back (paperback novel, released before the movie came out), and it was my first experience with eating a microwave pizza (which was an extraordinarily mushy thing). I think we just had a few hours between trains, we had time to get off and go up to the top of the Sears Tower. Later went to the top of the Empire State Building.

It felt like the Sears Tower was swaying, while the Empire State Building was more steady. I can't remember if we went to the WTC, probably did.

It was a neat experience at the time, but like everything else I suspect it wouldn't be that fun now.

We made that trip a few times as a family in a Ford LTD Station Wagon, green with the wood trim panels. I remember sitting way in the back of that critter, in the little fold-up seats, eating the frick out of poptarts and playing some vertical pinball game (that probably drove my dad insane).
Years later my brothers and I made the same trip in a 1984 Mustang, got to Buffalo in 17 hrs. I almost got us killed in Ohio on the interstate, they let me drive through heavy construction areas.

Took me forever to understand Ohio wasn't simply fricking cornfields after that run.

Even later, made the run with my fiance in her Mercury Cougar, we broke down in Memphis and rolled almost to Graceland. Later lost the cruise control for good in Kentucky.

Drives didn't go to Chicago, but a more normal and straight route. North-South through Miss, East-West through Tennessee... couple of long states.