Route 66 Self-Drive in Reverse – Los Angeles to Chicago

Day 1 UK to Los Angeles

Today begins the start of your journey by boarding your international flight from the UK to Los Angeles. On arrival, collect your hire car from the airport and drive to your centrally located hotel. Los Angeles, known as the City of Angels, is synonymous with movie stars and Hollywood glitz. This sprawling metropolis is a melting pot of cultures complete with stunning beaches and world-class shopping and art galleries. This evening, make the most of the city’s incredible dining options then possibly opt to sip cocktails at a rooftop bar. (N)

Accommodation in Los Angeles: Hilton Garden Inn Hollywood
Upgrade option: Best Western Sunset Plaza Hotel
Alternative upgrade option: Roosevelt Hollywood

Day 2 Los Angeles

You have a full free day today to explore Los Angeles and the surrounding areas. Go star-spotting in Beverly Hills, take an electric bike tour of Venice Beach or a sunset hike in the Hollywood Hills. If you want to make the most of your hire car, drive further afield to the beautiful Orange County beaches of Huntington or Newport and experience that laidback LA lifestyle. Los Angeles also has a thriving food scene offering anything from delicious food-truck delicacies to Michelin star sushi restaurants. (N)

Accommodation in Los Angeles: Hilton Garden Inn Hollywood
Upgrade option: Best Western Sunset Plaza Hotel
Alternative upgrade option: Roosevelt Hollywood

Day 3 Los Angeles to Las Vegas – 280 miles

The start of your reverse Route 66 road trip starts today and why not begin at the iconic Santa Monica Pier, which is usually the finish point of the Mother Road drive. Wind your windows down and enjoy the first stretch of open road as you leave LA behind and approach the desolate Californian countryside. Before you reach the California-Nevada border it is worth stopping at Mojave National Park, a vast land of desert, colourful canyons and rugged mountains. Continue your drive through Nevada until the bright lights of Vegas come into view. Check into your hotel located on the famous ‘Strip’. (N)

Accommodation in Las Vegas: Excalibur Hotel & Casino
Upgrade option: Luxor Las Vegas
Alternative upgrade option: Bellagio Las Vegas

Day 4 Las Vegas

Today you have a full free day where you can revel in all the glitz and glamour of Las Vegas. Explore the neon-lit Strip, waltz in and out of the finest casinos or catch some rays at the hotel pool, cocktail in hand. Vegas offers a huge variety of world-class theatre and concert performances and we can help with arranging tickets to your desired show before you depart for your trip. (N)

Accommodation in Las Vegas: Excalibur Hotel & Casino
Upgrade option: Luxor Las Vegas
Alternative upgrade option: Bellagio Las Vegas

Day 5 Las Vegas to Peach Springs – 157 miles

Say goodbye to the bright lights of Vegas as you continue your journey to Peach Springs. As you head over the Nevada-Arizona border stop off at the Hoover Dam, the famous arch-gravity dam situated in the Black Canyon of the Colorado River. Another two-hour drive and you will arrive in the small town of Peach Springs located on the original section of Route 66. Here you will stay at a quirky lodge with a Native American theme and retro diner. (N)

Accommodation in Peach Springs: Hualapai Lodge

Day 6 Peach Springs to Flagstaff – 113 miles

On your way to Flagstaff stop off at Seligman, a retro Mother Road town filled with neon signs, nostalgic treasures and classic cars. Once you have arrived in Flagstaff and checked into your hotel, you may wish to spend the remainder of the afternoon exploring some nearby natural wonders including the Coconino National Forest and Walnut Canyon National Monument. (N)

Accommodation in Flagstaff: Best Western Pony Soldier Inn
Upgrade option: Little America

Day 7 Flagstaff

Enjoy a full day in Flagstaff or explore the surrounding area. The Grand Canyon is approximately an 80-mile drive so today is a great opportunity to experience one of the Seven Wonders of the Natural World. Marvel at the spectacular views across the Canyon, hike through well-trodden trails or take a helicopter ride over the North or South Rim. (B)

Accommodation in Flagstaff: Best Western Pony Soldier Inn
Upgrade option: Little America

Day 8 Flagstaff to Holbrook – 91 miles

Check out of your hotel this morning and hop back in the car to continue your reverse Route 66 journey towards Holbrook. Holbrook is a small city in Navajo County in Arizona and tonight you will be staying in the iconic, but basic, Wigwam Motel complete with tipis to sleep in. Before arriving in Holbrook stop off in Winslow and visit the nearby Meteor Crater landmark, a meteorite impact crater that rocked the Southwest over 50,000 years ago. (B)

Accommodation in Holbrook: Wigwam Motel

Day 9 Holbrook to Gallup – 96 miles

Departing Holbrook, drive through the otherworldly Petrified Forest National Park which is home to the world’s largest collection of petrified wood, or stop off at the Painted Desert, a vast and beautiful landscape of colourful rocky Badlands. Continue your journey where you will enter New Mexico and arrive at the historic Route 66 city of Gallup. Tonight, stay at the famous El Rancho, a popular hotel for 1940s movie stars filming Westerns. (N)

Accommodation in Gallup: El Rancho

Day 10 Gallup to Albuquerque – 140 miles

This morning start the two-hour drive to Albuquerque passing hot and dusty desert and historic Route 66 road signs and markings. On arrival, explore New Mexico's largest city and, should you wish to, ride the Sandia Peak Aerial Tramway. Enjoy a spectacular view of the Rio Grande Valley from the observation deck and don’t miss the sunset where the desert produces a myriad of colours and light. (N)

Accommodation in Albuquerque: Navito Lodge
Upgrade option: Best Western Rio Grande

Day 11 Albuquerque to Amarillo – 287 miles

Today you might choose to experience the Santa Fe Loop of Route 66 – drive to Santa Fe with its Spanish Hacienda style architecture and historic plaza, next head to Santa Rosa and its Route 66 Auto Museum before continuing via the fading neon lights of Tucumcari towards Texas. As you advance to the Texan border, stop off at the ghost town of Glenrio before arriving at the official Mother Road midpoint town of Adrian, a great Route 66 photo opportunity. Continue your journey to Amarillo where you will be staying for the night. (N)

Accommodation in Amarillo: Big Texan Motel (or similar)

Day 12 Amarillo to Oklahoma City – 260 miles

As you check out of your hotel in Amarillo why not visit Cadillac Ranch, one of Route 66’s most famous attractions featuring 10 half-buried graffiti-covered Cadillacs. Palo Duro Canyon State Park, the second largest canyon in the US, is also a worthy stop-off. Crossing the border, Oklahoma contains more still-drivable miles of the old highway than any other state. Stop in the city of Clinton which is home to one of the best-rated Route 66 museums or take a detour to Edmond to photograph the Arcadia Round Barn. That evening, experience Oklahoma City’s warm Southern hospitality and discover a wealth of new restaurants and food trucks. (N)

Accommodation in Oklahoma City: Best Western Saddle Back Inn (or similar)

Day 13 Oklahoma City to Springfield, Missouri – 286 miles

Leaving Oklahoma City, stop off in in Tulsa which is home to beautiful art deco buildings from the 1930s and then continue to some of Route 66’s most iconic landmarks such as the Blue whale in Catoosa or Ed Galloway’s Totem Pole Park in Foyil. Cross into Kansas where you will follow the historic road for just 13-miles and then arrive in Missouri and make your way to Springfield for the evening. (B)

Accommodation in Springfield, Missouri: Best Western Route 66 Rail Haven (or similar)

Day 14 Springfield, Missouri to St. Louis – 215 miles

Continue your Route 66 in reverse journey onto St. Louis, the Gateway of the West. En-route, stop at Cuba or Rolla or discover the Meramec Caverns which are a spectacular 4.6-mile cave system that was formed from the erosion of large limestone deposits over millions of years. This afternoon, explore St. Louis; head to the top of the iconic Gateway Arch for sensational views of the city, catch a Cardinals baseball game and sample some of the country’s best frozen custard at Ted Drewes. (B)

Accommodation in St. Louis: Hampton Inn Gateway Arch (or similar)

Day 15 St. Louis to Springfield, Illinois – 97 miles

A short drive today will take you from St. Louis to Springfield, Illinois, the penultimate stop on your Route 66 adventure. On arrival in Springfield follow in the footsteps of President Abraham Lincoln and discover where his political career began by visiting the Presidential Museum or Lincoln Home National Historic Site. (B)

Accommodation in Springfield, Illinois: Hampton Inn Springfield IL (or similar)
Upgrade option: President Abraham Lincoln

Day 16 Springfield, Illinois to Chicago – 205 miles

Leaving Springfield, start the final stretch of your reverse Route 66 journey towards Chicago. Stop in Pontiac at the Route 66 Hall of Fame, home to historic memorabilia and artefacts, drive through Wilmington to catch a glimpse of the Gemini Giant muffler man and pass through Joliet to photograph the Neo-Baroque style Rialto Square Theatre. As the soaring skyscrapers and the glistening Lake Michigan come into view, welcome to Chicago. Drop off your rental car and make your way to your hotel before exploring Chicago’s impressive food and drink scene. (N)

Accommodation in Chicago: Best Western River North Hotel (or similar)
Upgrade option: Raffaello Hotel
Alternative upgrade option: Palmer House Hilton

Day 17 Chicago

Today you have a free day to explore cosmopolitan Chicago. The third largest city in the USA offers an excellent range of museums and art galleries, world-class shopping, exciting sporting events and endless choices of jazz and blues music venues. Explore the Art Institute of Chicago, shop and dine in the history-packed stretch ‘The Magnificent Mile’, wander through the landscaped gardens in Millennium Park or catch a Chicago Bulls basketball game. (N)

Accommodation in Chicago: Best Western River North Hotel (or similar)
Upgrade option: Raffaello Hotel
Alternative upgrade option: Palmer House Hilton

Day 18 Chicago to the UK

Enjoy your final morning at leisure in the Windy City before making your way to Chicago International Airport where you will board your international flight back to the UK. (N)

Day 19 Arrive UK

Arrive back into the UK in the morning. (N)

Self-Drive: Route 66 in Reverse – Los Angeles to Chicago

19 days from £1821 per person

Itinerary Highlights

Itinerary: Self-Drive: Route 66 in Reverse – Los Angeles to Chicago

What To Do Next?

What's included

What's not included

Guide to Price

What Is A Tailor-Made Holiday?

View On The Map

USA - Route 66 Holiday Review

Related Blog Posts

21 Top Things to See & Do on Route 66