Chicago to Toronto drive with stop in Detroit

  • 3 Stops
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Embark on a road trip from the bustling cityscape of Chicago, Illinois to the cosmopolitan charm of Toronto, Ontario, with a memorable stopover in Detroit, Michigan. Following the route along the Great Lakes, you will witness a blend of vibrant city life, industrial history, and natural beauty.

Start in Chicago, a city known for its architecture, deep-dish pizza, and blues music. You could kick off the road trip with a drive along the iconic Lake Shore Drive, offering panoramic views of the Chicago skyline and Lake Michigan.

Heading east, your next stop is Detroit. Known as the Motor City, Detroit is a testament to America’s automobile and Motown music heritage. The Detroit Institute of Arts, Detroit Historical Museum, and the Motown Museum are just a few must-visit sites.

Continuing across the border into Canada, you’ll reach Toronto. As Canada’s largest city, Toronto is a bustling metropolis brimming with culture, art, and diverse food scenes. The CN Tower, Royal Ontario Museum, and the Distillery Historic District are only a few of the city’s highlights.

1 Chicago, IL

The Windy City offers an array of attractions, from world-class museums and restaurants to vibrant neighborhoods and outdoor spaces. Marvel at the skyline from Navy Pier or enjoy a picnic in Millennium Park. Don’t miss the Art Institute of Chicago, and be sure to try the city’s famous deep-dish pizza and Chicago-style hot dogs.

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2 Detroit, MI

The birthplace of the American automobile industry, Detroit has rich history and culture. Visit the Detroit Institute of Arts, explore the Detroit Historical Museum, and discover the city’s music history at the Motown Museum. Enjoy Detroit’s revitalized downtown area with its eclectic mix of restaurants, bars, and shops.

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3 Toronto, ON

Known for its diversity and culture, Toronto offers everything from art and music to food and sports. Ascend the CN Tower for a bird’s eye view of the city, explore the Royal Ontario Museum, or take a ferry to the Toronto Islands. The St. Lawrence Market and the Distillery District are must-visit spots for food lovers.

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