Pittsburgh to Chicago road trip with stop in Cleveland

  • 3 Stops
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Travelers looking for a scenic road trip will find that the journey between Pittsburgh, Pennsylvania and Chicago, Illinois offers plenty of beautiful views. The route takes travelers through the rolling hills of the Appalachian Mountains and along the shores of Lake Erie. There are also several stops in small towns and cities along the way, including Cleveland, Ohio. In Cleveland, travelers can explore the city’s many museums and historical sites. The road trip ends in Chicago, where travelers can enjoy the city’s skyline and architecture. With so much to see and do, this road trip is sure to please travelers of all ages.

1 Pittsburgh, PA

Known as the “Steel City,” Pittsburgh is a city of bridges, hills, and sports. Its rich industrial history can be explored at the Carnegie Museum of Natural History and the Heinz History Center. The city’s North Shore is home to both the Pittsburgh Steelers and Pirates, offering a vibrant sports culture. The Strip District offers an eclectic mix of markets, while the views from the Duquesne Incline are not to be missed.

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2 Cleveland, OH

Cleveland is a vibrant lakeside city with a love for music and sports. The Rock and Roll Hall of Fame is a must-visit for music enthusiasts, showcasing the most influential figures in the industry. Sports fans will enjoy visiting the FirstEnergy Stadium, home of the Cleveland Browns. The city’s diverse culinary scene ranges from high-end dining to local delights like the Polish Boy sandwich.

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3 Chicago, IL

The Windy City, perched on Lake Michigan, is renowned for its bold architecture, deep-dish pizza, and jazz music. Visit the Art Institute of Chicago, stroll along the Navy Pier, or enjoy the view from the SkyDeck at Willis Tower. Don’t miss the Millennium Park, home to the reflective “Bean” sculpture, and be sure to try local culinary staples, like a Chicago-style hot dog or an Italian Beef sandwich.

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