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10-Day Route 66 Road Trip Adventure Itinerary

Last updated: 2024 Jun 14

Exploring Springfield's Historic Sites

Morning

Start your day with a hearty breakfast at Gailey's Breakfast Cafe, a local favorite known for its delicious breakfast options.

Afternoon

Spend the afternoon exploring the Route 66 Car Museum. This museum features an impressive collection of classic cars and memorabilia from the historic Route 66.

Evening

Enjoy a fine dining experience at Flame Steakhouse and Wine Bar, renowned for its steaks and extensive wine list.

Bedtime

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Natural Wonders of Springfield

Morning

Begin your day with a visit to Fantastic Caverns. This unique cave tour is conducted entirely by jeep-drawn trams, making it accessible and enjoyable.

Afternoon

Have lunch at Black Sheep Burgers and Shakes, famous for its gourmet burgers and creative shakes.

Evening

Dine at Gilardi's Ristorante, an Italian restaurant known for its authentic dishes and cozy atmosphere.

Bedtime

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Route 66 Highlights in Springfield

Morning

Visit the History Museum on the Square to learn about Springfield's rich history and its connection to Route 66.

Afternoon

Grab lunch at Cafe Cusco, offering delicious Peruvian cuisine in a vibrant setting.

Evening

End your day with dinner at The Order, located in Hotel Vandivort. Enjoy modern American cuisine in a stylish setting.

Bedtime

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Chicago Bound via Route 66

Morning

Depart Springfield early and head towards Chicago along Route 66. Stop by the iconic Gemini Giant statue in Wilmington for a quick photo op.

Afternoon

Arrive in Chicago and have lunch at Portillo's Hot Dogs, famous for its Chicago-style hot dogs and Italian beef sandwiches.

Evening

Catch a show or enjoy live music at House of Blues, one of Chicago's premier entertainment venues.

Bedtime

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Exploring Downtown Chicago

Morning

Start your day with a visit to Millennium Park to see the famous Cloud Gate sculpture (The Bean) and enjoy the beautiful park surroundings.

Afternoon

Have lunch at Girl & The Goat, known for its innovative small plates and vibrant atmosphere.

Evening

Take an evening stroll along the Chicago Riverwalk before dining at Alinea, one of Chicago’s most acclaimed restaurants offering an unforgettable culinary experience.

Bedtime

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Chicago’s Cultural Gems

Morning

Visit the renowned Art Institute of Chicago to explore its vast collection of art from around the world.

Afternoon

Enjoy lunch at The Purple Pig, offering Mediterranean-inspired dishes perfect for sharing.

Evening

Skydeck Chicago at Willis Tower (Sears Tower) offers breathtaking views of the city skyline; follow this up with dinner at Lou Malnati's Pizzeria to try some iconic deep-dish pizza.

Bedtime

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