I know, I know—flying is faster. But let’s be honest: by the time you Uber to JFK, wait in the security line, and deplane at O’Hare, you’ve burned four hours anyway. The train? It takes about 19 hours, which sounds bonkers until you realize you’re seeing the entire country scroll by your window while you sip a glass of wine.
Plus, no one ever tells you, “My favorite part of the flight was the pretzels.” But on the train? People rave about the dining car. It’s basically a moving diner with better views.
The Train: Meet the Lake Shore Limited
Your chariot on this journey is Amtrak’s Lake Shore Limited. It departs from New York’s majestic Moynihan Train Hall (formerly the glorious Penn Station—still smells like pretzels and ambition). Then it chugs through the Hudson Valley, past Albany, and into the heart of the Midwest.
The name “Lake Shore Limited” sounds like a luxury yacht, but don’t worry—it’s more “cozy rolling hotel” than “floating palace.” And that’s the charm. You get a seat, a snack, and a front-row ticket to America’s backyard.