Our Epic Route 66 Road Trip: From Chicago to Santa Monica
Embarking on a journey along the legendary Route 66 is the ultimate road trip adventure, our latest trip was with Judy, Tina, David, John and Gary in a White Suburban covering the 2400 miles and our experience from Chicago to Santa Monica was nothing short of extraordinary.

Starting in the Windy City
Our journey began in Chicago, where we took in the city’s towering skyscrapers, and arts in the park and with the car packed and spirits high, we set off on Route 66, ready to explore the heart of America.
Passing Through the Heartland
As we drove through Illinois, we marveled at our first taste of Americana at Joliet and the Polka Dot drive-in. The first main stop was at the cozy town of Pontiac, a town of murals and where the Route 66 Hall of Fame and Museum gave us a fascinating glimpse into the history of this iconic highway.
Springfield, Illinois
Near Springfield, we visited the Muffler Men and Cozy Dog Cafe. We also made sure to grab a bite at the Ariston Cafe at a classic Route 66 diner, where the retro ambiance took us back in time.
Crossing the Mississippi River
Entering Missouri, we crossed the mighty Mississippi River and arrived in St. Louis. The Gateway Arch greeted us, standing tall as a symbol of westward expansion.
The Ozarks and Beyond
Driving through the rolling hills of the Ozarks, we experienced the natural beauty of Missouri. We stopped at Meramec Caverns, a stunning cave system that once served as a hideout for the infamous outlaw Jesse James only to find it flooded by unusually heavy rain. Unpreturbed we headed west to Cuba and the world largest Rocking Chair at Fanning.
The Plains of Oklahoma
Oklahoma offered us the charm of small towns and the vastness of the plains. We visited the Cadillac Ranch and delved into the nostalgic allure of the Mother Road. The friendly locals and their stories of Route 66’s heyday added a personal touch to our journey.
The Landscapes of the Southwest
As we continued into Texas, New Mexico, and Arizona, the landscape transformed into a desert wonderland. We marveled at the vast open spaces, quirky roadside attractions, and the beautiful sandstone formations of the Petrified Forest National Park. We added a detour to Monument Valley and stayed at Kayenta to take in the sunrise.
The Grand Canyon State
Arizona treated us to awe-inspiring natural wonders. We detoured to visit the Grand Canyon, where the breathtaking views left us speechless. Further along Route 66, we stopped in the charming towns of Williams and Seligman, a treasure trove of Route 66 memorabilia and nostalgia.
California Dreamin’
Our final stretch took us through the Mojave Desert and into California. The excitement built as we approached our destination. Kingman and the legendary Mr Dz for the best milkshake on the trip to the Wild West town of Oatman followed by the dessert towns of Goffs, Fenner and The Bagdad Cafe gave a different vibe to this diverse trip.
Ending in Santa Monica
Arriving at the Santa Monica Pier marked the end of our Route 66 adventure. The iconic pier, with its vibrant lights and ocean views, was the perfect place to reflect on our incredible journey. We dipped our toes in the Pacific Ocean, celebrating the completion of our coast-to-coast trip.
Memories for a Lifetime
Our road trip along Route 66 was more than just a drive; it was an exploration of America’s diverse landscapes, cultures, and history. Each stop offered a unique glimpse into the past and present of this iconic highway, leaving us with memories that will last a lifetime.
Join us for our next trip in 2026. Click here to find out more about all our USA tours.
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