Book a roomette if you can. Yes, it costs more (typically $200–$400 extra), but it includes meals in the dining car, a private compartment, and a fold-down bed. It turns the trip from an endurance test into a cozy retreat. If you’re on a budget, the coach seats recline far and are surprisingly spacious—but pack a neck pillow and an eye mask.
Bring your own snacks. The café car sells microwaved pizzas and bags of chips, but the real treasure is the dining car breakfast. The French toast is famously good, partly because you’re eating it while watching cows in Pennsylvania. Also: pack a refillable water bottle. Train air is dry, like airplane air but with more ambient sway.
My 19-hour train ride from NYC to Chicago: A pilgrimage of sorts
Don’t forget entertainment. There’s spotty Wi-Fi through most of New York and Illinois, but the middle 600 miles is a dead zone. Download two movies, bring a thick book, or—and this is the move—pack a journal. The rhythm of the tracks is perfect for writing down half-formed thoughts you’ve ignored for months.