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Ultimate American Road Trip on Route 66 Itinerary

Last updated: 2024 Jun 14

Iconic Start in the Windy City

Morning

Start your legendary American road trip with a hearty breakfast at the historic Lou Mitchell's, a Route 66 classic. Afterward, take a leisurely walk around Millennium Park and marvel at the famous Cloud Gate sculpture, also known as "The Bean."

Afternoon

For lunch, savor the deep-dish pizza at Pizzeria Uno, a Chicago institution. Post that, explore the fascinating exhibits at the Art Institute of Chicago, one of the oldest and largest art museums in the country.

Evening

Conclude your day with a delightful dinner at The Signature Room on the 95th floor of the John Hancock Center, offering stunning views of the city skyline. Afterward, take a stroll along the Navy Pier and enjoy the vibrant atmosphere.

Bedtime

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Historic Journey to Springfield

Morning

Enjoy a classic American breakfast at Charlie Parker's Diner, a local favorite. Then, immerse yourself in history with a visit to the Abraham Lincoln Presidential Library and Museum.

Afternoon

For lunch, try the famous horseshoe sandwich at D'Arcy's Pint. Afterward, explore the Lincoln Home National Historic Site and the Old State Capitol.

Evening

Dine at the cozy Maldaner's Restaurant, known for its farm-to-table cuisine. Take a leisurely walk around the downtown area and soak in the historic charm of Springfield.

Bedtime

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Gateway to Fun in St. Louis

Morning

Start your day with a visit to the Gateway Arch, an iconic symbol of the westward expansion of the United States. Afterward, have a delightful brunch at Rooster, known for its crepes.

Afternoon

Explore the City Museum, a one-of-a-kind attraction with a mix of playground, funhouse, and architectural marvel. For lunch, enjoy the local favorite, toasted ravioli, at Charlie Gitto's on the Hill.

Evening

Dine at the famous Blueberry Hill, a landmark restaurant and music club. Afterward, take a walk in the Delmar Loop area, known for its vibrant street life and live music venues.

Bedtime

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Art and Culture in Tulsa

Morning

Begin your day with a visit to the Philbrook Museum of Art, a beautiful mansion with extensive art collections and lush gardens. For a delightful breakfast, head to Tally's Good Food Cafe.

Afternoon

Enjoy a leisurely lunch at the Chimera Cafe, known for its eclectic menu and artistic vibe. Spend the afternoon exploring the Woody Guthrie Center and the Tulsa Art Deco Museum.

Evening

Dine at the trendy Juniper Restaurant, which focuses on local and seasonal ingredients. Afterward, take a walk along the Arkansas River and enjoy the scenic views.

Bedtime

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Texan Flavors in Amarillo

Morning

Start your day with a visit to the Cadillac Ranch, a unique art installation on Route 66. For breakfast, enjoy the classic Texan dishes at the Big Texan Steak Ranch.

Afternoon

Afterward, explore the Panhandle-Plains Historical Museum to learn about the history of Texas and the surrounding region. For lunch, try the famous 72-ounce steak challenge at the Big Texan.

Evening

Conclude your road trip with a farewell dinner at the iconic Golden Light Cafe, a historic Route 66 eatery. Enjoy the live music and the company of fellow travelers as you reminisce about your journey.

Bedtime

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