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Route 66 Adventure - 5 Days Itinerary

Last updated: 2024 Jun 14

Kickoff in Chicago

Morning

Start your Route 66 adventure in the Windy City, Chicago. Begin your day with a visit to the iconic Route 66 Start Sign. This is where the historic journey begins, and it's a must-see for any Route 66 traveler. After snapping some photos, head over to Lou Mitchell's, a classic diner that's been serving breakfast to Route 66 travelers since 1923.

Afternoon

After breakfast, explore downtown Chicago. Visit Millennium Park and see the famous Cloud Gate sculpture (also known as 'The Bean'). Then take a stroll along the Magnificent Mile for some shopping and sightseeing. For lunch, stop by Giordano's for some of Chicago's famous deep-dish pizza.

Evening

In the evening, catch a show at one of Chicago's renowned theaters or enjoy live music at a local jazz club. For dinner, head to The Purple Pig, known for its Mediterranean-inspired small plates and vibrant atmosphere.

Bedtime

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Exploring Illinois

Morning

Leave Chicago early and drive towards Springfield, Illinois. Your first stop should be at the Gemini Giant in Wilmington - one of the classic 'Muffler Men' statues that dot Route 66. Enjoy breakfast at Old Route 66 Family Restaurant in Dwight.

Afternoon

Continue your journey south with stops at Pontiac to visit the Route 66 Hall of Fame & Museum and see their amazing murals. Have lunch at Bernardi's II Restaurant which offers great Italian cuisine.

Evening

Arrive in Springfield by evening and check into your hotel. Explore downtown Springfield and visit Lincoln’s Home National Historic Site if time permits. For dinner, try out Maldaner's Restaurant, one of Illinois' oldest restaurants offering farm-to-table dining.

Bedtime

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Historic Missouri

Morning

Depart from Springfield early morning heading towards St. Louis, Missouri. Stop by Henry’s Rabbit Ranch in Staunton which features VW Rabbits instead of real ones! Have breakfast at Country Classic Cars Cafe nearby.

Afternoon

Arrive in St Louis by afternoon; visit Gateway Arch – an iconic symbol of westward expansion offering stunning views over Mississippi River & city skyline from its top observation deck! Enjoy lunch at Pappy’s Smokehouse – famous BBQ joint loved by locals & tourists alike!

Evening

Spend evening exploring Laclede’s Landing district filled with cobblestone streets lined with bars/restaurants housed within restored warehouses dating back late-19th century era; dine-in Broadway Oyster Bar known not only fresh seafood but also live music performances making it perfect spot end day!

Bedtime

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Oklahoma City Highlights

Morning

Start your day with a visit to the Oklahoma City National Memorial & Museum, a moving tribute to the victims of the 1995 bombing. This site offers a poignant and reflective experience. For breakfast, head to Kitchen No. 324, known for its delicious pastries and hearty breakfast options.

Afternoon

After the museum, take a stroll through Bricktown, Oklahoma City's entertainment district. Here you can enjoy a canal ride or visit the American Banjo Museum. For lunch, stop by Fuzzy's Taco Shop for some tasty Tex-Mex cuisine.

Evening

In the evening, explore the vibrant Paseo Arts District, home to numerous galleries and studios. Enjoy dinner at The Mule, famous for its gourmet grilled cheese sandwiches and craft beers.

Bedtime

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Journey Through Texas

Morning

Cadillac Ranch awaits you as you enter Amarillo. This public art installation features half-buried Cadillacs covered in graffiti – feel free to add your own mark! For breakfast, visit Ye Olde Pancake Station, known for its hearty portions and friendly service.

Afternoon

The Big Texan Steak Ranch is a must-visit for lunch – try their famous 72-ounce steak challenge if you're up for it! Afterward, explore Historic Route 66 District with its antique shops & quirky boutiques offering unique souvenirs!

Evening

Texas Air & Space Museum offers fascinating exhibits on aviation history; spend evening here before heading back hotel relax after long day travel! Dine-in at Embers Steak House which serves excellent steaks & seafood dishes ensuring perfect end day!

Bedtime

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