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5 Days Ultimate Route 66 Road Trip Adventure Itinerary

Last updated: 2024 Jun 29

Kicking Off in Chicago

Morning

Start your journey at the iconic Route 66 Begin Sign. This is the official starting point of Route 66 and a must-see for any road trip enthusiast. Capture some photos and soak in the history of this legendary highway.

Afternoon

Head over to Willis Tower Skydeck for a breathtaking view of Chicago from above. The Skydeck offers panoramic views that stretch across four states on a clear day. It's an excellent way to get a sense of the city's layout before hitting the road.

Evening

Conclude your first day with a visit to Navy Pier. This bustling waterfront area is perfect for an evening stroll, offering everything from restaurants and shops to entertainment options. Enjoy dinner at Giordano's, famous for its deep-dish pizza.

Bedtime

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Exploring Springfield

Morning

Drive to Springfield, Illinois, home of Abraham Lincoln. Start your day with a visit to the Lincoln Home National Historic Site. This preserved neighborhood offers a glimpse into Lincoln's life before he became president.

Afternoon

After lunch at Cozy Dog Drive In, known for its corn dogs, head over to the Illinois State Capitol. The building's architecture is stunning, and guided tours provide insight into Illinois' political history.

Evening

Spend your evening exploring the quirky side of Route 66 with a stop at The Lauterbach Giant. This roadside attraction is one of many 'Muffler Men' statues scattered along Route 66 and makes for great photo opportunities.

Bedtime

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St. Louis Gateway Arch Adventure

Morning

Arrive in St. Louis and start your day with a visit to the iconic Gateway Arch. Take the tram ride to the top for unparalleled views of the city and Mississippi River.

Afternoon

After descending from the arch, enjoy lunch at Pappy's Smokehouse, renowned for its Memphis-style BBQ. Then head over to Missouri Botanical Garden, one of the oldest botanical institutions in America.

Evening

Wrap up your day with some live music at BB's Jazz Blues and Soups, a local favorite that offers great food and even better tunes.

Bedtime

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Discovering Tulsa's Charm

Morning

Start your day in Tulsa with a visit to the Philbrook Museum of Art. This museum is housed in a beautiful Italian Renaissance villa and features an impressive collection of art, as well as stunning gardens.

Afternoon

After enjoying lunch at Tally's Good Food Cafe, known for its classic American diner fare, head over to the Golden Driller. This towering statue is one of the most iconic landmarks in Tulsa and pays homage to the city's oil-rich history.

Evening

Conclude your day with a stroll through the Guthrie Green, a vibrant urban park that often hosts live music and events. Enjoy dinner at The Tavern, which offers a modern twist on classic comfort food.

Bedtime

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Oklahoma City's Highlights

Morning

National Cowboy & Western Heritage Museum is a must-visit in Oklahoma City. Spend your morning exploring its extensive exhibits that celebrate the American West's history and culture.

Afternoon

Cattlemen's Steakhouse is perfect for lunch, offering some of the best steaks in town. Afterward, visit the Oklahoma City National Memorial & Museum. This poignant site honors the victims of the 1995 bombing and provides deep insights into this tragic event.

Evening

Bricktown is where you'll want to spend your evening. This lively entertainment district features restaurants, bars, and even a canal with boat rides. Enjoy dinner at Mickey Mantle's Steakhouse before wrapping up your night.

Bedtime

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