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Route 66 Adventure - 5 Days Itinerary

Last updated: 2024 Jun 14

Kicking Off in Chicago

Morning

Start your Route 66 adventure in Chicago, the official starting point of the historic highway. Begin your day with a hearty breakfast at Lou Mitchell's, a classic diner known for its delicious pancakes and omelets. Afterward, head to Route 66 Start Sign to take some iconic photos and officially mark the beginning of your journey.

Afternoon

Spend your afternoon exploring some of Chicago's famous attractions. Visit Millennium Park to see the famous Cloud Gate sculpture (The Bean) and enjoy a leisurely stroll through Grant Park. Don't miss out on the Art Institute of Chicago, one of the oldest and largest art museums in the United States. For lunch, stop by Girl & The Goat for some innovative American cuisine.

Evening

As evening approaches, make your way to Navy Pier for some fun and entertainment. Enjoy stunning views of Lake Michigan from the Ferris wheel or catch a live performance at one of the pier's theaters. For dinner, indulge in deep-dish pizza at Giordano's, a Chicago staple. End your night with a cocktail at The Aviary, an upscale bar known for its creative drinks.

Bedtime

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Exploring St. Louis

Morning

Drive from Chicago to St. Louis (approximately 4-5 hours). Upon arrival, start your day with breakfast at Blueprint Coffee, known for its artisanal coffee and pastries. Head over to visit Gateway Arch, an iconic symbol of St. Louis and Route 66.

Afternoon

In the afternoon, explore Forest Park, home to several attractions including the St. Louis Zoo and the Missouri History Museum. Have lunch at Pappy's Smokehouse, famous for its mouth-watering BBQ ribs and pulled pork sandwiches.

Evening

In the evening, visit The Loop neighborhood for some vibrant nightlife and entertainment options. Dine at Pi Pizzeria for some delicious thin-crust pizza before heading to Blueberry Hill, a legendary music club where you can enjoy live performances.

Bedtime

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Discovering Springfield

Morning

Drive from St. Louis to Springfield (approximately 1 hour). Start your day with breakfast at Lulu's Diner, known for its hearty breakfast options including biscuits and gravy or pancakes.

Afternoon

Spend your afternoon visiting historical sites such as Abraham Lincoln Presidential Library and Museum as well as Lincoln Home National Historic Site where you can learn about Lincoln’s life before he became president.

Evening

For dinner head over to Cozy Dog Drive In which is famous as it claims it invented corn dogs! After dinner take a stroll around downtown Springfield enjoying local shops cafes bars etc.

Bedtime

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Oklahoma City Highlights

Morning

Start your day with a delicious breakfast at Kitchen No. 324, known for its fresh pastries and hearty breakfast options. Afterward, visit the National Cowboy & Western Heritage Museum, where you can explore exhibits showcasing the history and culture of the American West.

Afternoon

In the afternoon, head to Bricktown, a lively entertainment district in downtown Oklahoma City. Take a leisurely stroll along the Bricktown Canal and enjoy lunch at Fuzzy's Taco Shop, which offers a variety of tasty tacos and Tex-Mex dishes. Don't miss the chance to visit the Myriad Botanical Gardens, a beautiful urban park with lush gardens and walking paths.

Evening

As evening approaches, make your way to the Oklahoma City National Memorial & Museum to pay your respects and learn about the events of April 19, 1995. For dinner, dine at Cattlemen's Steakhouse, an iconic restaurant known for its perfectly cooked steaks. End your night with a drink at The Jones Assembly, a trendy bar with live music and craft cocktails.

Bedtime

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Exploring Amarillo

Morning

Cadillac Ranch is an absolute must-see when in Amarillo! Start your day by visiting this unique public art installation featuring half-buried Cadillacs covered in graffiti art. For breakfast, stop by Ye Olde Pancake Station for some classic pancakes and hearty breakfast fare.

Afternoon

Palo Duro Canyon State Park awaits you in the afternoon! Known as the 'Grand Canyon of Texas,' this stunning park offers hiking trails with breathtaking views of colorful rock formations. Pack a picnic lunch from The Bagel Place to enjoy amidst nature's beauty.

Evening

Big Texan Steak Ranch is an iconic Route 66 attraction that you can't miss! Head there for dinner and try their famous 72-ounce steak challenge if you're up for it. Afterward, explore downtown Amarillo's nightlife scene by visiting some local bars like Hoots Pub or catching live music at Golden Light Cantina.

Bedtime

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