The Ultimate Route 66 Road Trip Adventure Chicago to Los Angeles

Few journeys carry the same spirit of freedom as a drive along Route 66. Starting in Chicago, you will set out westward on a road that has captured the imagination of travellers for generations. This 16-night adventure takes you through eight different states, each with its own landscapes, flavours, and stories to tell.

Further west, the scenery changes dramatically. New Mexico greets you with desert landscapes, Native American culture, and striking sunsets, while Arizona delivers dramatic canyons and wide-open skies. A detour to the Grand Canyon is highly recommended, giving you one of the world’s most breathtaking natural wonders just off your route.

Finally, after miles of open road and countless memories, you will arrive in California. Los Angeles marks the end of your journey, with its golden beaches, Hollywood history, and lively streets bringing your road trip to a fitting close.

This package is designed to give you both comfort and flexibility. Hotels are included for each stop along the way, ensuring you always have a welcoming place to rest after a day of driving and exploring. Car hire is provided, giving you the freedom to travel at your own pace, stopping wherever the road tempts you — whether it’s a classic diner, a quirky roadside attraction, or a scenic lookout across the desert.

Route 66 is more than a drive; it is a journey through the heart of America. From the nostalgia of old service stations to the modern energy of major cities, it blends history and adventure into one unforgettable experience. This holiday brings you closer to the true spirit of the open road — the freedom to travel, to explore, and to create lasting memories mile after mile.

• Return flights from the UK to Chicago and from Los Angeles
• 16 nights’ hotel accommodation along Route 66
• Car hire for the full duration of the road trip
• Pre-planned route guidance with suggested stops and highlights
• Freedom to explore at your own pace along America’s most famous road

This holiday is not just about getting from one city to another; it’s about living the true spirit of adventure. Driving Route 66 is one of those experiences that stays with you forever. Every mile brings something different, whether it’s a classic diner serving homemade pie, a neon-lit motel that looks like it belongs in a movie, or the endless views of desert and sky. By booking this package, you are choosing an organised yet flexible journey. Flights, hotels, and car hire are taken care of, which means you can focus on enjoying the road without worrying about the details.

The package also gives you the perfect balance of comfort and freedom. With pre-arranged hotels, you’ll always have a place waiting for you at the end of each day, yet you are free to stop whenever you wish, explore hidden corners, and take detours to see sights such as the Grand Canyon. It is a safe, comfortable, and well-planned way to take on one of the most legendary road trips in the world.

This special package is set for 1 December 2025, a wonderful time to experience Route 66. Travelling at this time of year brings cooler weather compared to the summer months, making long drives more comfortable and sightseeing easier. You’ll also avoid the peak tourist season, which means quieter attractions, shorter queues, and a more peaceful atmosphere along the route.

December in the Midwest can bring crisp air and festive charm, while the further west you drive, the warmer the days become. By the time you reach Arizona and California, you’ll enjoy mild sunny days that are perfect for exploring the outdoors. Arriving in Los Angeles in December also means you get to experience the city’s festive atmosphere, with decorated streets, lively events, and the glow of the holiday season.

Travelling at this time gives you a unique view of Route 66, with fewer crowds and the added magic of America in the run-up to Christmas. It’s a rare chance to see this famous road in a quieter, more relaxed light.