Upstate NY, This Is The Coolest Amtrak Trip You Can Take

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Amtrak is one of the best ways to “city-hop” in Upstate New York. Anyone can enjoy the architecture of Buffalo, the nightlife of Rochester, the micro hot spot of Schenectady (and more!) by jumping on a train instead of white-knuckling it down I-90.

But if you live in Upstate/Western New York, by far and away the most interesting whirlwind weekend trip you can take on a budget is to the Windy City of Chicago. Skeptical of the long ride? Hear me out.

From my hometown of Rochester, I can leave on Amtrak’s Lake Shore Limited at 11:12pm on a Friday night. The train travels overnight and arrives in Chicago at 10am on Saturday morning. For about 12 hours, I can enjoy the many wonders, museums, parks, eateries and attractions of Chicago’s downtown until the Lake Shore Limited departs Union Station back to Rochester at 9:30pm. Once again, the train travels overnight and arrives back in Rochester at 9:48am Sunday morning. The trip will cost you $152 round trip, and since you there’s no need for lodging while in Chicago, that’s you’re only “travel cost.”

Imagine taking a trip from New York to Chicago in a weekend, still having time at home on Sunday, and best of all, being able to tell your co-workers about your Chicago adventure at the water cooler on Monday morning after they tell you about the exciting time they had mowing the lawn or cleaning their gutters.

Yes, the trip is long, and sleeping on the train isn’t always the easiest experience (though the wealth of leg room makes it far better than a plane!) but if you don’t mind roughing it for a little adventure, this trip is one of the most uniquely interesting ones you can take for not a lot of money. I’ve personally made this trip many times and I’ve had a blast every single time.

Go for it. A fun day in Chicago is waiting for you! PS – To see all the photos I took the last time I made this trip, click here!