Historic Route 66

Fly to Chicago, Illinois then pick up your rental car and check in to your hotel in Chicago. Spend the afternoon at leisure before you start your road trip tomorrow. Head to Millennium Park to see the iconic Cloud Gate, and stroll through Grant Park and the nearby Buckingham Fountain. Explore the architectural wonders along the Chicago Riverwalk and take a river cruise for city views.

ACCOMMODATION: 4* The Ambassador, Chicago or similar

This morning you will begin your epic road trip along Route 66; the drive from Chicago to Springfield is a nostalgic journey through Americana.

Starting from the bustling streets of Chicago, you soon find yourself on the historic Mother Road. Pass through quaint towns like Joliet, home to the Rialto Square Theatre, and Wilmington, where the towering Gemini Giant beckons. In Pontiac, visit the Route 66 Hall of Fame and Museum. The countryside is dotted with vintage gas stations and diners. In Atlanta, witness the Paul Bunyon statue holding a giant hot dog.

Finally, arrive in Springfield, rich with Abraham Lincoln history and Route 66 memorabilia, completing a picturesque drive through Illinois’s heartland.

ACCOMMODATION: 3* President Abraham Lincoln Springfield, DoubleTree or similar

DRIVING TIME: 5 hrs / 215 mi

Before leaving Springfield, visit Oak Ridge Cemetery where you can see the Lincoln Tomb, the final resting place of President Abraham Lincoln and his family.

Stop in Litchfield to explore the Litchfield Museum and Route 66 Welcome Centre, and have lunch in the historic Ariston Café. In Staunton, the Henry's Rabbit Ranch offers quirky roadside charm and then the landscape transitions to rolling hills and lush forests. Stop in Edwardsville to explore its quaint downtown.

As you approach St. Louis, the iconic Gateway Arch rises on the horizon. Cross the Mississippi River, arriving in the vibrant city known for its blues music, barbecue, and rich history, perfectly blending the old Route 66 charm with urban excitement.

ACCOMMODATION: 4* The Pennywell St Louis Downtown or similar

DRIVING TIME: 2.5 hrs / 106 mi

Start your day in St. Louis with a visit to the Gateway Arch for breathtaking views from the top. Next, explore the nearby Old Courthouse, rich in history. Head to the City Museum, an imaginative and interactive wonderland perfect for all ages. Enjoy lunch at a local eatery in the Delmar Loop, followed by a visit to the Missouri Botanical Garden for a peaceful stroll through its beautiful landscapes. Spend the afternoon at Forest Park, exploring the St. Louis Zoo and the St. Louis Art Museum. Conclude your day with dinner in the vibrant Soulard district, enjoying live music and local cuisine.

ACCOMMODATION: 4* The Pennywell St Louis Downtown or similar

Today you will drive from St Louis to Springfield, through the heart of the Ozarks and small towns like Pacific and Cuba, where vintage murals and the World's Largest Rocking Chair await. Stop in Rolla to explore its Route 66 connections and picturesque scenery, and pick up some sweet treats at Uranus Fudge Factory and General Store in St Robert. Visit Lebanon's Route 66 Museum for a dose of nostalgia.

As you approach Springfield, MO, the landscape features rolling hills and lush forests. Springfield offers Route 66 landmarks like the Gillioz Theatre and the Birthplace of Route 66 Roadside Park.

ACCOMMODATION: 3* Best Western Route 66 Rail Haven, Springfield or similar

DRIVING TIME: 5.5 hrs / 237 mi

Spend the morning at the Route 66 Car Museum in Springfield before heading back on the road towards Tulsa.

Pass through charming towns like Carthage, known for its classic Route 66 attractions, including the Red Oak II art village and the 66 Drive-In Theatre. In Joplin, visit the Route 66 Mural Park, before stopping for lunch at the Old Riverton Store. Continue through the scenic Ozark landscape, then head into Oklahoma. Stop in Miami for a view of vintage Route 66 signs and the iconic Coleman Theatre, and then onto Ribbon Road, the narrowest and oldest segment of Route 66. Look out for the Blue Whale in Catoosa, just on the outskirts of Tulsa.

Arriving in Tulsa, enjoy the vibrant arts scene, explore the historic downtown, and visit the Route 66 Historic District, experiencing a rich tapestry of roadside history and culture.

ACCOMMODATION: 3* Hyatt Place Tulsa Downtown or similar

DRIVING TIME: 5 hrs / 205 mi

Take the morning to explore Tulsa further, including Buck Atom’s Cosmic Curios and the iconic Cyrus Avery Route 66 Memorial Bridge.

In Arcadia, check out the historic Round Barn and pop into the old-fashioned Pops Soda Ranch for a refreshing treat, with over 600 choices of soda pop.

Arrive in Oklahoma City to experience its vibrant Bricktown district and rich Route 66 heritage. Visit the National Cowboy & Western Heritage Museum, stroll through the Myriad Botanical Gardens and wrap up your day with dinner and entertainment in Bricktown, where you can savour diverse cuisine and lively nightlife, reflecting the city's dynamic spirit.

ACCOMMODATION: 3* Best Western Plus Saddleback Inn & Conference Centre, Oklahoma City or similar

DRIVING TIME: 2.5 hrs / 115 mi

Depart Oklahoma City and head west, passing through classic Route 66 towns like El Reno and Hydro. In Clinton, stop at the Oklahoma Route 66 Museum before crossing into Texas. Don’t miss the Leaning Tower of Texas in Groom, and the VW Slug Bug Ranch in Conway.

Arriving in Amarillo, explore landmarks like the Cadillac Ranch, where colourful cars are buried in the desert, and the historic Big Texan Steak Ranch for a hearty meal. The drive blends rich history with striking landscapes, marking a memorable segment of Route 66.

ACCOMMODATION: 3* Best Western Santa Fe, Amarillo or similar

DRIVING TIME: 4.5 hrs / 248 mi

Leaving Amarillo you will pass Midpoint Café in Adrian, the halfway point of Route 66 and as you approach New Mexico you will travel through the historic ghost town of Glenrio. Stop for lunch in Tucumcari, renowned for its vintage motels and neon signs. In Santa Rosa, explore the Blue Hole, a stunning natural swimming hole.

Arriving in Santa Fe, immerse yourself in its rich cultural heritage, from the historic Plaza to the vibrant art galleries and Pueblo-style architecture.

ACCOMMODATION: 3* The Lodge at Santa Fe or similar

DRIVING TIME: 4.5 hrs / 284 mi

ACCOMMODATION: 3* Best Western Plus Rio Grande Inn, Albuquerque or similar

DRIVING TIME: 1 hr / 64 mi

ACCOMMODATION: 3* Best Western Plus Gallup Inn & Suites or similar

DRIVING TIME: 2.5 hrs / 140 mi

ACCOMMODATION: 4* High Country Motor Lodge, Flagstaff or similar

DRIVING TIME: 3.5 hrs / 199 mi

ACCOMMODATION: 4* High Country Motor Lodge, Flagstaff or similar

ACCOMMODATION: 3* Gateway Hotel Santa Monica or similar

DRIVING TIME: 4.5 hrs / 158 mi

Today you fly back to the UK, dropping the car back at Los Angeles airport.

Your overnight flight arrives back in the UK for you to make your journey home. 

Route 66 traverses over 2,400 miles, across 8 states and 3 time zones, so you will experience a lot of different landscapes and climates. Spring and Autumn are the best times to travel for mild weather and quieter roads. Avoid the peak of summer as temperatures can get very hot and during winter, snow may close some portions of the road.

Please note to rent a car the lead driver must have a credit card in their name. Debit cards are only accepted in some cases. We recommend GPS and zero excess is included in the car rental, other options include multiple drivers and a full tank of petrol, which will be discussed when making your booking. Many of the roads are so vast and straight in the national parks you’d be forgiven for thinking it’s okay to drive a little faster than you actually should. There are, however, a lot of police cars and speed checks along the roads so do ensure you stick to the speed limit, which can often be 50 or 55 miles an hour. A one way fee may be applicable to the car rental, which will need to be paid on arrival. This will be confirmed at the time of booking.

Some of the areas you'll be travelling are quiet remote, you may like to bring with you lots of water and snacks.

Around National Parks and near remote areas, the standard of accommodation is fairly basic. Treat them just as a place to sleep, as you won't be spending much time in them.

British citizens do not require a VISA to visit the US, but they do need to apply online for an electronic authorization (ESTA). https://esta.cbp.dhs.gov/

Most U.S. National Parks charge an entrance fee, typically around USD $20–$35 per vehicle. From 1 January 2026, the “America the Beautiful” Annual Pass will cost USD $250 for non-U.S. residents, which provides access to most National Parks. In addition, non-U.S. residents without an annual pass will pay a USD $100 per person surcharge to enter 11 of the most visited national parks, on top of standard entrance fees. Find more information at: https://www.nps.gov/planyourvisit/passes.htm