Don’t worry—you don’t need to dress like a 1920s film star. Jeans and a hoodie work fine. But do pack a few critical items: a good book, a notebook, and snacks that aren’t just pretzels. The café car has hot dogs and microwaved pizza, but trust me—bring your own fancy cheese and crackers.
Chicago to New York Train - Amtrak Tickets $108 | Wanderu
The trip takes about 19 to 20 hours, leaving New York in the late afternoon and arriving in Chicago the next morning. That sounds long, but think about it: you’re sleeping through the dull parts. Book a roomette if you want a private cocoon; otherwise, coach seats recline far back and come with a little footrest. It’s like a slumber party on wheels.
You’ll arrive at Chicago’s Union Station, a grand Beaux-Arts temple, just as the city wakes up. Step off the train, and you’re five minutes from the Art Institute, the “Bean,” or a world-class Italian beef sandwich. The transition from the quiet hum of the rails to the energy of the Loop is seamless, and you feel it in your bones.
The Real Reason to Do This
Here’s the secret: train travel is a lesson in presence. When you fly, you’re trying to get somewhere faster. When you take the Lake Shore Limited, you’re already there—there in the moment, watching the landscape roll by like a slow, beautiful scroll.
You return home not just with a souvenir, but with a new rhythm in your step. You’ve proven to yourself that you can slow down, that the journey matters as much as the destination. And isn’t that a little bit like life itself?
So go ahead—book that ticket. Pack your curiosity and a sense of wonder. Let the train do the driving while you do the living. I promise you’ll arrive in Chicago feeling more refreshed, more connected, and more alive than you ever would from a cramped airplane seat. And who knows? You might just fall in love with the ride.
