New York City to Chicago road trip with stop in Cleveland

  • 3 Stops
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Embark on an exciting road trip from New York City, NY, to Chicago, IL, featuring a delightful stopover in Cleveland, OH.

Setting off from the bustling heart of New York City, take I-80 W, a direct route through Pennsylvania’s scenic landscapes. As you pass through the Pocono Mountains and the rolling hills of rural Pennsylvania, the urban jungle gives way to serene countryside.

Your halfway point is the vibrant city of Cleveland on the southern shore of Lake Erie. Take a break to explore the Rock and Roll Hall of Fame, soak in the city’s rich industrial history, or indulge in its emerging foodie scene.

As you continue your journey towards Chicago, the road takes you around the southern edge of Lake Michigan. The city skyline suddenly appearing on the horizon is a sight to behold. Known for its architectural marvels, blues music, and distinctive culinary creations (like the deep-dish pizza), Chicago blends Midwestern charm with metropolitan flair.

1 New York, NY

Known as ‘The Big Apple’, New York City is an epicenter of arts, culture, and fashion. From iconic sights like the Statue of Liberty and Central Park to the neon lights of Times Square and Broadway’s marquees, NYC thrums with unmatchable energy. Its neighborhoods are a global feast for the senses, offering diverse food, music, and festivities.

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2 Cleveland, OH

Nestled on the shores of Lake Erie, Cleveland is a dynamic city with a strong cultural vibe. It’s the home of the Rock and Roll Hall of Fame and the historic West Side Market. With a blossoming food scene, an array of craft breweries, and rich sports traditions, Cleveland offers unexpected surprises at every corner.

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3 Chicago, IL

The ‘Windy City’ stands out for its unique skyline, marked by architectural gems like Willis Tower and Navy Pier. Chicago’s art scene is vibrant, punctuated by the Art Institute of Chicago’s world-class collection. Its rich blues heritage, delectable deep-dish pizza, and legendary sports teams all contribute to the city’s distinct charm.

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