Has anyone taken the City of New Orleans train to Chicago?

Yes, in a roomette. General summary, not comparable (obviously) to flying, longer than driving but way better, you can relax, read, sleep do whatever. Food included in room, decent quality, and can bring your own stuff. Also get dropped off right in the loop, so no train or car ride from airport into city.

Not cheap in roomette, think it was $400ish one way years ago, however not as bad considering I would spend $200-$300 driving it after gas, food and one night hotel stay.

The worst 19 hours of my life. You could fly back and forth between the two cities 6 times and pay about the same.

Yup. frick KANKAKEE, IL.

Took it a bunch of times when I was younger from around age 8-14. Then we would connect up with Empire Builder and go west. It was a blast when I was young. The observation car was always really cool.

Fast forward to a couple of years ago and I took the train again and it wasn't nearly as awesome being older. It costs more than a flight, takes longer, and most of the line from Hammond to Chicago is boring.

The scenery is still great on Empire Builder, but the price is crazy for a roomette.

The condition of the tracks makes it impossible to sleep.
At times, it is dangerous to walk around.