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Scenic Road Trip from Chicago to Cleveland Itinerary

Last updated: 2024 Jun 14

City Sights and Lakefront Drive

Morning

Start your day with a delicious brunch at Lula Cafe, known for its farm-to-table dishes. Afterward, take a leisurely drive along the Lakefront Trail, passing by Navy Pier and the Adler Planetarium. Enjoy the stunning views of Lake Michigan and the city skyline.

Afternoon

For lunch, stop at Portillo's Hot Dogs for a classic Chicago meal. Afterward, visit the iconic The Magnificent Mile for some leisurely shopping and a glimpse of the city's famous architecture, including the Wrigley Building and the Tribune Tower.

Evening

In the evening, head to 360 Chicago Observation Deck (Formerly John Hancock Observatory) for a panoramic view of the city at sunset. Afterward, enjoy a relaxing dinner at The Signature Room at the 95th, where you can savor fine dining with a view.

Bedtime

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Brew City Exploration

Morning

After a scenic drive to Milwaukee, start your day with a hearty brunch at Blue's Egg. Then, visit the historic Milwaukee Art Museum and take a stroll along the Lakefront Trail.

Afternoon

For lunch, try the famous custard at Kopp's Frozen Custard. Afterward, explore the Historic Third Ward with its unique shops and galleries. You can also visit the Harley-Davidson Museum for a taste of American motorcycle history.

Evening

Enjoy a relaxing dinner at Mader's, a classic German restaurant in Milwaukee. Afterward, take a scenic drive around the city to see the lights and waterfront views.

Bedtime

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Architectural Marvels and Skyline Views

Morning

Have a leisurely breakfast at Lou Malnati's Pizzeria to fuel up for the day. Then, take the Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's iconic buildings and history.

Afternoon

For lunch, enjoy a deep-dish pizza at Pequod's Pizza. Afterward, visit the Art Institute of Chicago to admire its world-class art collection, including the famous "American Gothic" painting.

Evening

In the evening, take a sunset cocktail cruise on the Chicago River with Chicago River Guided Sunset Cocktail & Architecture Tour. After the cruise, have a gourmet dinner on a Chicago Gourmet Brunch, Lunch, or Dinner River Cruise, enjoying the city's skyline from the water.

Bedtime

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Culinary Delights and Skydeck Views

Morning

Start your day with a delightful brunch at Little Goat Diner, a popular spot for creative comfort food. Then, visit the Willis Tower Skydeck and The Ledge to get a bird's eye view of the city.

Afternoon

For a late lunch, indulge in a gourmet experience at Alinea, one of the top restaurants in the world. Afterward, take a relaxing walk in Millennium Park and see the famous Cloud Gate.

Evening

End your trip with a memorable dinner at Au Cheval, known for its delicious burgers. Afterward, take a stroll along the Chicago Riverwalk to enjoy the city lights reflected on the water.

Bedtime

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