Route 66 Classic Trail
Route 66 road trip holiday including the Grand Canyon and Las Vegas
Set out on the legendary Route 66 Classic Trail, a 14-night adventure that captures the very best of America’s Mother Road. Beginning in Chicago, this fast-paced journey leads you through bustling cities, small-town Americana, neon-lit main streets and sweeping desert landscapes as you make your way to the Pacific Coast. Along the way you’ll discover roadside diners, retro motels, iconic museums and timeless attractions that continue to inspire travellers from around the world.
From the historic brick roads of Illinois to the mighty Mississippi at St Louis, the rolling Ozarks of Missouri and the cowboy culture of Oklahoma, each day reveals a new chapter in Route 66 history. You’ll stand at the midpoint in Texas, soak up adobe charm in New Mexico, explore the colours of the Painted Desert, and spend a night near the South Rim of the Grand Canyon before rolling into the bright lights of Las Vegas. Your trip ends at the Santa Monica Pier, where the Pacific Ocean marks the perfect finale to this unforgettable cross-country drive.
Ideal for travellers wanting to experience Route 66’s full spirit in just two weeks, this holiday blends iconic highlights with hand-picked accommodation in prime locations — from Chicago’s Magnificent Mile to the Las Vegas Strip. With endless roadside discoveries and a full road-trip pack to guide your adventure, the Classic Trail delivers the quintessential Route 66 experience from start to finish.
Remember: We’re UK-based, and every holiday we create is fully flexible – you can add nights, upgrade hotels, or enhance your itinerary. We love designing tailor-made self-drive adventures just for you!
14 night self drive holiday from £1,999pp including flights, accommodation & car rental
Highlights
Drive the full Mother Road from Chicago to Santa Monica, passing iconic towns, diners and neon landmarks.
Witness sunrise at the Grand Canyon, one of the most spectacular natural sights in the world.
Stay two nights on the Las Vegas Strip, surrounded by dazzling entertainment and desert scenery.
Explore New Mexico’s classic Route 66 stops, including Tucumcari, Santa Fe or Albuquerque, and the dramatic Painted Desert.
Your itinerary
DAYs 1-2: discover CHICAGO
Start your Route 66 holiday in Chicago, the beginning of the Mother Road. Explore the best of the Windy City with iconic views, museums, and the Magnificent Mile.
Arrive in Chicago, Illinois, pick up your car, and settle in for two nights in the vibrant city where Route 66 begins. Stroll along the shores of Lake Michigan, explore lively downtown streets, and feel the pulse of this world-class metropolis. As evening falls, indulge in Chicago’s iconic deep-dish pizza or enjoy live blues in one of its legendary clubs. Spend the following day taking in the city’s highlights — ride to the top of the Willis Tower or the 360 Chicago Observation Deck for sweeping skyline views, then wander the Magnificent Mile, brimming with shops, restaurants, and architectural gems. Don’t miss Millennium Park and its reflective “Bean” sculpture, a symbol of the city’s creativity and style. With its dazzling energy and urban charm, Chicago provides the perfect start to your Route 66 adventure.
2 Nights in
Chicago, IL
Arrive &
Explore
DAY 3: CHICAGO TO SPRINGFIELD, ILLINOIS
Begin your Route 66 adventure through Illinois to Springfield, land of Abraham Lincoln.
Leave Chicago and officially begin your drive along Route 66, passing small towns, classic diners, and restored gas stations. Your destination is Springfield, the state capital, where Abraham Lincoln once lived. Visit Lincoln’s Home National Historic Site, explore the Old State Capitol, and pay your respects at his tomb in Oak Ridge Cemetery. Springfield offers a blend of history and Route 66 nostalgia.
1 Night in
Springfield, IL
200 miles
DAY 4: SPRINGFIELD TO ST. LOUIS, MISSOURI
Drive the original brick road to St. Louis and see the mighty Gateway Arch.
Today’s short drive takes you south to St. Louis, Missouri. En route, you can still drive a section of the original brick Route 66 in Auburn, a true throwback to the road’s early days. Walk across the historic Chain of Rocks Bridge over the Mississippi River before arriving in St. Louis. The highlight here is the Gateway Arch, America’s tallest monument, symbolizing the city’s role as the Gateway to the West.
1 Night in
St Louis, MO
100 miles
DAY 5: ST. LOUIS TO SPRINGFIELD, MISSOURI
Travel through the Ozarks to the birthplace of Route 66.
Continue southwest through the rolling Ozark Mountains, dotted with small towns, vintage motels, and roadside diners. Arrive in Springfield, Missouri, where in 1926 the route connecting Chicago and Los Angeles was officially named Route 66. Visit the Route 66 Car Museum and enjoy the nostalgic charm of Springfield, the birthplace of the Mother Road.
1 Night in
Springfield, MO
215 miles
DAY 6: SPRINGFIELD TO OKLAHOMA CITY
Cross three states in one day, including Kansas’ short but famous stretch of Route 66.
Today’s drive is one of the most varied, taking you through Missouri, a 13-mile stretch of Route 66 in Kansas, and into Oklahoma. Don’t miss the legendary Sidewalk Highway, a narrow nine-foot-wide piece of original road surface between Miami and Afton. Arrive in Oklahoma City, where modern culture blends with cowboy heritage.
1 Night in
Oklahoma City, OK
285 miles
DAY 7: OKLAHOMA CITY TO AMARILLO, TEXAS
Discover museums, art-deco landmarks, and Cadillac Ranch in Amarillo.
Head west across the Great Plains into Texas. Stop at the Route 66 Museum in Clinton to learn about the history of the road, and admire the striking art-deco U-Drop Inn in Shamrock. End the day in Amarillo, where you’ll visit the surreal and colorful Cadillac Ranch, one of Route 66’s most famous roadside attractions.
1 Night in
Amarillo, TX
260 miles
DAY 8: SANTA FE OR ALBUQUERQUE
Drive Route 66 to Santa Fe or Albuquerque. Experience New Mexico culture, adobe architecture, and even Breaking Bad filming spots.
Continue along Route 66 to Adrian, Texas, the official midpoint, for a fun photo stop. Crossing into New Mexico, you’ll pass Glenrio’s ghost town and Tucumcari’s neon-lit motels, a classic 1950s Route 66 stop. From here, follow the original 1926 alignment to Santa Fe, known for its adobe architecture and vibrant art scene, or the later route to Albuquerque, with its Old Town charm and pop-culture sites like Breaking Bad locations. Either way, you’ll discover New Mexico’s unique blend of Native American, Hispanic, and Western culture.
1 Night in Santa Fe or
Albuquerque, NM
280 miles
DAY 9: HEAD TO HOLBROOK VIA PETRIFIED FOREST
See vintage motels, desert landscapes, and the Petrified Forest.
Drive west past Grants and Gallup, towns filled with vintage motels and Route 66 character. Crossing into Arizona, explore the incredible Petrified Forest National Park and the colorful Painted Desert, a unique highlight of the road. Continue on to Holbrook, where you can stay in a historic motel that embodies the spirit of Route 66.
1 Night in
Holbrook, AZ
295 miles
DAY 10: HOLBROOK TO THE GRAND CANYON
Stand on the corner in Winslow before reaching the Grand Canyon South Rim.
Stop at the quirky Jack Rabbit Trading Post and pose at the “Standin’ on the Corner” park in Winslow, made famous by the Eagles. From there, head to the spectacular Grand Canyon, where your hotel is minutes from the South Rim. Be sure to rest up — you’ll want to wake early to catch the unforgettable sunrise tomorrow.
1 Night at
Grand Canyon, AZ
170 miles
DAYs 11-12: GRAND CANYON TO LAS VEGAS
See sunrise at the Grand Canyon, then drive via Hoover Dam to Las Vegas where you can enjoy shows, casinos, and desert adventures.
Rise early to witness a breathtaking sunrise over the Grand Canyon, a moment that captures the true spirit of your Route 66 adventure. After soaking in the views, drive west toward Las Vegas, pausing to marvel at the engineering wonder of the Hoover Dam. As you arrive, the desert gives way to a neon paradise of dazzling lights, luxury resorts, and world-class entertainment. Spend the next day discovering all that Las Vegas has to offer — from glamorous casinos and spectacular shows to fine dining and shopping along the Las Vegas Strip. For a change of pace, venture out to Red Rock Canyon to experience the rugged beauty of the Mojave Desert. Whether you seek excitement or escape, Las Vegas delivers it in unforgettable style.
2 Nights in
Las Vegas, NV
275 miles
DAYs 13-14: LAS VEGAS TO SANTA MONICA
Drive the final stretch of Route 66 to the Pacific Ocean.
Leave the glittering lights of Las Vegas behind and journey west into California, passing through classic Route 66 towns like Barstow and Victorville, where the California Route 66 Museum celebrates the road’s golden age. Your adventure culminates at the Santa Monica Pier, the official “End of the Trail,” where the Pacific Ocean glistens beneath the iconic sign. Capture the moment with a photo, stroll the boardwalk, or ride the historic carousel as sea breezes mark the perfect finale to your cross-country odyssey. Spend two nights embracing the glamour of Los Angeles — shop on Rodeo Drive, admire the views from Griffith Observatory, or hike to the Hollywood Sign. For film fans, visit locations from Back to the Future, Grease, and Duel, or simply relax by the beach.
2 Nights in
Santa Monica, CA
270 miles
May- Jun & Sept- Oct: Weather is likely to be pleasant for the entire trip. The midwest shouldn’t be too cold and the southwestern states shouldn’t be too hot.
We would expect maximum temperatures to be in the 20°C - 30°C range in the midwest and 25°C - 35°C in the south and southwestern states
Flight times to/from Chicago is around 8 hours and Los Angeles is approx 11 hours. You’ll drive through 3 time zones. Chicago is 5 hours and Los Angeles is 8 hours behind the UK.
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