Arrive at Chicago's O'Hare International Airport, where you can then make your way to your hotel at your own pace. Whether you choose a taxi, ride-sharing service, or public transportation, the vibrant city awaits your exploration.

Immerse yourself in the splendour of the Windy City, exploring its vast expanse and hidden gems. Begin your journey at the intersection of Michigan and Adams, the renowned starting point of the iconic Historic Route 66. Delight in a hearty breakfast at Lou Mitchell’s, a beloved Chicago staple since 1923 and a rite of passage for Route 66 wanderers. As you meander along the lakefront, indulge in some retail therapy, savour a quintessential Chicago Dog, or cycle through the city's lush parks. Dive deep into Chicago's rich history and marvel at its architectural wonders, including the towering Willis Tower, one of North America's loftiest structures.

As you collect your rental car, feel the anticipation of embarking on an iconic journey through the pages of America's history along the famed Route 66. This storied highway, a symbol of vintage Americana, winds through picturesque landscapes and showcases some of the nation's most renowned, ancient, and quirky landmarks.

Set off on Route 66's classic east-to-west path, journeying from Chicago to St. Louis, Missouri. As you drive, the vast expanses of cornfields and serene prairies stretch out before you. Along the way, be sure to pause and capture a moment with Wilmington's iconic Gemini Giant, an impressive green statue, and Atlanta’s towering Bunyan Giant, where the famed Paul Bunyan proudly presents a colossal hot dog.

In Springfield, treat yourself to a bite at the Cozy Dog Drive-In, celebrated as the birthplace of the corn dog. While there, delve into the enduring legacy of Abraham Lincoln by visiting the Lincoln Home National Historic Site.

When you reach St. Louis, the grandest city on Route 66, step into the shoes of historic explorers. The city brims with significant sites, not least of which is the Gateway Arch, standing tall as the nation's highest monument. Immerse yourself in its rich heritage and stories that echo through time.

Journey through the scenic Ozark Highlands of southern Missouri, making your way to Springfield, heralded as the birthplace of Route 66. Along your path, pause to explore the Meramec Caverns, a vast network of natural limestone caves. Their stunning formations and vibrant hues captivate the eye and the imagination. As you wander these subterranean marvels, discover the intriguing history they hold — the notorious Jesse James once sought refuge here, using the cave's underground river as a covert escape route.

This morning, carve a path through the southeastern slice of Kansas, setting your sights on Oklahoma City. Notably, Oklahoma boasts the longest drivable stretch of Route 66 compared to any other state. This includes several unique miles of the original 9-foot-wide road segment, a testament to the resilience of Oklahoman families who journeyed westward in the 1930s, seeking brighter futures on the horizon of the Dust Bowl era.

As you journey towards Oklahoma City, take a detour to marvel at the whimsical 20-foot cement Blue Whale in Catoosa, a cherished landmark on Route 66. Further along, pay tribute at the Cyrus Avery Route 66 Memorial Bridge in Tulsa. These landmark honours the enduring legacy of the man affectionately known as the "Father of Route 66" and his profound influence on this iconic roadway.

Upon reaching Oklahoma City, the heart of the state, immerse yourself in the rich tapestry of its history. The city beckons with its array of classic Route 66 motels, time-honoured gas stations, and a myriad of vintage buildings that echo the tales of a bygone era.

Journey onward to Amarillo, nestled within the flat expanses of the Texas Panhandle. This stretch of Texas once flourished as the buffalo-abundant grasslands of the Great Plains, echoing with the footfalls of the Kiowa and Comanche tribes who called it home.

As you traverse this historic landscape, make a pit stop at the Route 66 Museum in Clinton. Here, you'll be transported through time, exploring six decades of Route 66's storied past. Continue your exploration with a visit to Shamrock’s Tower Station and the adjacent U-Drop Inn Cafe. Their art deco designs and prominent spire stand as enduring symbols of the bustling era they once dominated.

Journey further to encounter the beautifully restored first Phillips 66 gas station in McLean, a nod to the golden age of road trips. As you pass through Groom, two distinctive landmarks will catch your eye: a curiously leaning water tower and an impressive 150-foot tall stainless steel cross, both casting their unique silhouettes against the Texan sky.

Upon your arrival in Amarillo, don't miss out on the famed Big Texas Steak Ranch. If you're feeling particularly audacious, try your hand (or rather, your appetite) at their 72oz. steak challenge. A true test for even the most dedicated carnivores!

Before setting off from Amarillo, don't miss the iconic Cadillac Ranch. This one-of-a-kind art installation boasts ten vibrantly painted Cadillac cars, nose-dived into the ground, offering a surreal yet captivating sight. Afterward, make your way to the MidPoint Café in Adrian, renowned for its delightfully named “ugly crust” pies—a must-try for every traveller.

From Adrian, the allure of Route 66 beckons as it winds its way towards Albuquerque, New Mexico. Prepare to immerse yourself in the rich culture and mystique of the Land of Enchantment as your journey continues.

New Mexico's crown jewel, Albuquerque, stretches gracefully along the banks of the Rio Grande. Dedicate a day to discovering the gems along Downtown Albuquerque's Central Avenue, brimming with iconic Route 66 landmarks. Venture into Historic Old Town, where the echoes of New Mexico’s Spanish colonial heritage resonate. Meanwhile, the Indian Pueblo Cultural Centre, a collaboration of the state’s 19 distinct Pueblo communities, offers a deep dive into the rich tapestry of the region's Indigenous cultures and history.

For a genuine taste of the Old Route 66, make sure you take a detour to Santa Fe, the historic capital of New Mexico. Built upon the remnants of a once-abandoned Native American village, Santa Fe stands as the oldest capital in the U.S. While its alignment with Route 66 ceased in 1938, its charm remains undiminished, making it one of the most visually enchanting cities in the state. Historically, it marked the terminus of the ancient Santa Fe Trail, a pivotal trade route bridging the American eastern frontier with the distant west.

Delve into Santa Fe’s rich artistic legacy. From its renowned art galleries and vibrant art markets to its array of museums that house both traditional and contemporary masterpieces, the city is an art lover's paradise. Notably, it’s home to collections of the celebrated artist Georgia O’Keeffe.

As you journey into Arizona this morning, the state greets Route 66 adventurers with an array of inviting trading posts. Amid your travels, gaze upon the imposing concrete tepees that rise against the backdrop of vibrant red-rock mesas, a sight to behold. Your path leads you to the Petrified Forest National Park, a unique jewel in the National Park System that proudly houses a segment of Historic Route 66. Here, immerse yourself in over 13,000 years of human history, marvelling at a magnificent display of petrified wood, ancient structures, and archaeological wonders.

Before the day wanes, experience the ethereal beauty of a sunset cascading over the Painted Desert from the park’s Kachina Point, a sight that will etch itself into your memory. As night falls, make your way to Holbrook and nestle into the iconic Wigwam Motel. Recognizable by its steel and concrete teepees, this historic motel seamlessly melds vintage charm with modern comforts, having played host to weary travellers since the 1950s.

Journey onward to Meteor City, a quintessential vintage trading post whose unique dome stands as a beacon, visible for miles as you traverse this section of Route 66. As you weave your way through the picturesque towns of Flagstaff and Williams, you'll be on course to one of nature's most awe-inspiring masterpieces: Grand Canyon National Park. This monumental marvel is something that needs to be witnessed firsthand to truly grasp its magnificence.

Dedicate your day to exploring the iconic South Rim of the Canyon. Pause at any of the numerous vantage points, stroll along sections of the Rim Trail, or wander the historic Hermit Road. For those seeking that picture-perfect snapshot, visit one of the designated Photo Hot Spots. If you're up for a climb, ascend a stone Watchtower to be rewarded with sweeping panoramic vistas that, on clear days, span over a staggering 100 miles.

Set out from the quaint town of Williams, charting a course towards Seligman. This town marks the beginning of the westward journey on the most extensive continuous segment of Route 66. Proceed through Kingman, where the spirit of old Route 66 is still alive and well, reflected in its thriving cafés and motels.

Your journey will then unveil one of Arizona's gems, the Hoover Dam. Recognised as the most monumental public works project in U.S. history, this colossal dam dominates the Colorado River, creating a boundary between Nevada and Arizona. From there, set your sights on Las Vegas – a dazzling city that, with its glittering lights and iconic landmarks, needs no introduction.

Embrace the electrifying energy of Las Vegas for a full day. Stroll along the iconic Strip, where mega-resorts glisten under neon lights, tempting you with their allure. Test your luck at any of the city's renowned casinos, treat your palate to gourmet meals at top-tier restaurants, and get entranced by the latest blockbuster shows. From shopping in upscale boutiques to adrenaline-pumping rollercoaster rides, or simply lounging by a shimmering pool, Las Vegas offers an endless array of experiences.

Begin your day journeying through the vast expanse of the Mojave Desert, aiming for the Calico Ghost Town. Steeped in history, Calico stands as California's genuine remnant of silver mining days and remains as one of the few preserved mining camps from the Old West era.

Your journey leads you back to Route 66 in Barstow, where a visit to the Route 66 Mother Road Museum offers a rich tapestry of historic photographs and artifacts, narrating the stories of Route 66 and the communities of the Mojave Desert. From there, weave your way through the iconic landscapes of Pasadena, Los Angeles, West Hollywood, and the glitzy avenues of Beverly Hills, finally reaching Santa Monica.

Savour a day wandering the sandy shores of Santa Monica or perusing the eclectic blend of indoor and outdoor boutiques at Third Street Promenade. Dive deeper into L.A., exploring its unique landmarks, celebrity hotspots, and architectural wonders. If you're in the mood for cinematic magic, Universal Studios Hollywood is just a drive away. Alternatively, you can relive childhood dreams at Anaheim's original Disneyland Park, conveniently located within a short drive's reach.

Before taking off, return your rental car to Los Angeles International Airport. Wishing you a pleasant journey ahead!