Epic Route 66 Road Trip from Chicago to Los Angeles

The next two days are yours to spend discovering the scenic and cultural delights of the so-called ‘Windy City’. Nestled on the shores of Lake Michigan, Chicago is a vibrant cosmopolitan hub in a superb natural setting. On the streets, architects like Sullivan, Burnham and Frank Lloyd Wright have left their creative mark on the city, while on the shores of Lake Michigan lies Millennium Park, a sweeping green oasis filled with points of interest. There’s also an ever-present buzz of culture: stand-up shows on Broadway, intimate blues or jazz bars and the swirl of pride around the latest sport’s win. You’ll be armed with the Chicago Explorer Pass, which gives you access to three out of the thirty major sites across the city. We’ve also arranged for you to enjoy dinner and a show at Andy's Jazz Club, one of the most iconic and timeless jazz haunts of the South and West Sides. And finally, if you’re an architecture enthusiast, then our team will be happy to organise a thematic cruise on the Chicago River that centres around seeing some of the city’s most beautiful buildings from a privileged viewpoint.

It’s time to get some miles under your belt and start hitting the road west. Your next destination is Springfield, a historic city known for being the home of President Abraham Lincoln, a three-hour drive from Chicago. The journey passes though Chicago’s suburbs and later Cicero, a town frequented by the gangs of the Roaring Twenties. On arrival in Springfield, check in for the night in a contemporary hotel perfect for a quick and comfortable stopover.

Today you’ll be crossing state lines into Missouri, journeying an hour-and-a-half through the sweeping plains and small rural towns of the Midwest to St Louis. On arrival, check in for the night in a characterful hotel in the centre of town and spend the rest of today exploring the city. You’re in walking distance of some of the best sights, including Forest Park, the Loop district and Laclede's Landing. You’ll also be armed with entrance tickets to the Gateway Arch, the emblem of St Louis. The mind-bogglingly tall 630ft footbridge is the world’s tallest arch and, as the tallest building in the city, offers breathtaking views from the top.

After a hearty breakfast at the hotel this morning, hop back into your car and head southwest to another Springfield (it’s the most common place-name in the US), this time in Missouri. You’ll pass through some iconic landscapes along the way, including the Meramec Caverns, an ancient cave network that notorious outlaws Jesse and Frank James used as a hideout in 1870s, and the Ozark Mountains, which rose to fame as the backdrop of the hit Netflix crime drama of the same name. After three-and-a-half hours on the road you’ll arrive in Springfield, a classic midwestern city filled with the retro cinemas, diners, motels, gas stations and drugstores of yesteryear. Your home for the night is a simple yet stylish hotel with great service and a lovely bar and restaurant.

Your next destination on this great American road trip is Tulsa, in neighbouring Oklahoma, a charming city known for its concentration of art deco architecture in the central Deco District. The journey takes about three hours and winds through sleepy towns and sweeping forests, gently becoming more and more rural. On arrival in the city, settle in for one night in a delightful hotel in the heart of town. The rest of today is yours to spend discovering Tulsa. We recommend turning to our destination-specific Dossier of our top picks for cafes, restaurants and bars in the area to find somewhere fitting for some wining and dining this evening.

Before moving onto your fourth state, we have one more stop scheduled here in Oklahoma: the state’s capital, Oklahoma City. The drive shouldn’t take more than an hour and a half, leaving you plenty of time to delve into the city’s fantastic cowboy culture this afternoon. On arrival, check in for one night in a trendy hotel in the centre of the city. Once you’ve settled in and freshened up, it’s time to get exploring. One of our favourite spots is the National Cowboy Museum & Heritage Center, a wonderful museum magnifying the epic history of cattle, cowboys and rodeos in the West. You could also check out what’s going on in Stockyard City, which is home to the largest feeder cattle market in the world (on Mondays and Tuesdays), as well as a collection of restaurants, shops and other attractions. As for this evening, we recommend heading to Bricktown, an old warehouse district that has transformed into a hip canal-side neighbourhood known for its excellent evening entertainment options.

Your next stop along the iconic Route 66 is Amarillo, the ‘Yellow Rose of Texas’, a typical cowboy town located where the southern plains meet the desert. The journey takes a good four hours, passing through an ever drier desert landscape as you head directly west. As you drive into the city along Interstate 40, you’ll pass Big Texan Steak Ranch and Microbrewery, a classic Route 66 restaurant that has been relocated from its original spot to be easier to reach. After a hearty bit of food, head to your next accommodation, a comfortable contemporary hotel located in the heart of the city centre, where you’ll be staying for the night. We also recommend checking out 6th Street, a mile-long stretch of road that was on the original Route 66 and is now dedicated to the history and heritage of the route with shops, bars and restaurants.

Another day, another journey. Today you’ll be bidding Texas a warm farewell and crossing into neighbouring New Mexico. As you leave Amarillo, make sure to make an early pit stop at Cadillac Ranch, one of the most popular Route 66 monuments and public art installation that features ten colourful Cadillacs buried nose-down in a field at the same angle as the Pyramids of Giza. Your next destination is Tucumcari, a popular Route 66 hub located just under two hours away. You’ll be driving into the heart of Native America: New Mexico is home to 23 native communities that can be found in every corner of the state. In fact the name Tucumcari is derived from the native Comanche word for ‘lookout’ in reference to the nearby mountain that acted as a lookout for Comanche raiders preying on cowboys. On arrival in the city, settle in for one night in an iconic sixties-style motel that has hosted generations of Route 66 travellers.

It’s time to inch a little more west, but still within the borders of New Mexico. You guessed it… your next destination is the charming state capital of Santa Fe. The journey from Tucumcari takes just under three hours, however we recommend making a stop at Pecos National Historical Park to visit the fascinating ruins of an indigenous community known as the ‘village of 500 warriors’. Your home for the next two nights is a characterful hotel in the heart of town, close to lots of points of interest. The rest of today and tomorrow are yours to spend freely discovering the scenic and cultural delights of Santa Fe. You can while away hours drifting around the beautiful centre, admiring the many rustic adobe-clad houses and the exciting mixture of Hispanic and Native American architecture. There are also a host of independent art galleries worth visiting, as well as the Museum of Indian Arts and Culture, which traces the origin and history of various Native American peoples. When you’re ready to answer the call of the wild, head into the hills of the nearby Sangre de Cristo Mountains, the southernmost subrange of the Rocky Mountains, for a walk on one of the many well-signed hiking trails.

After a day’s break from driving, it’s time to hit the road again and rack up some more mileage on your voyage west. After a hearty breakfast this morning, hop back into your hire car and drive three hours to the small city Gallup, your final New Mexico destination. This portion of Route 66 feels like it hasn’t changed for decades: you’ll pass through Los Cerillos and Madrid, colourful ghost towns that treasure the remnants of the 70s hippy revolution, and bustling Albuquerque, which symbolises the Route 66 spirit with its diners adorned with spectacular signs. On arrival in Gallup, check in for the night in a simple yet classic hotel in the heart of town and spend the rest of the afternoon exploring the town. Gallup's Main Street is lined with colourful murals and Navajo craft shops, and is known and adored for being the location of the Inter-Tribal Indian Ceremonial parades, which take place in August and see all the native tribes and communities of the Americas meet and celebrate.

The time has come to leave New Mexico behind and cross into the sixth state of this epic Route 66 road trip: Arizona. Your next destination, the small town of Holbrook, is just an hour and a half’s drive away, giving you plenty of time to get a taste of local life in Arizona this afternoon. Set down your suitcases for one night in a comfortable hotel and spend the rest of today discovering the breathtaking natural landscapes that surround the town. One of the must-visits here is the Canyon de Chelly, a dramatic sandstone canyon that preserves centuries-old ancestral indigenous dwellings and rock art of the Anasazi ruins, an ancient Native American community. There is also the Petrified Forest National Park, which houses a large concentration of fossilised tree trunks, as well as fossils of a 220-million-year-old theropod dinosaur named Chindesaurus.

Rise and shine, it’s time to head to one of the most impressive natural wonders on Route 66 (and the Western Hemisphere): the Grand Canyon. Your base for the night is an elegant chalet-style motel in Tusayan, a lovely resort town two-and-a-half hours from Holbrook. Arizona's signature cacti expanses and desert landscapes gradually give way to pine forests, and temperatures cool as you approach the Grand Canyon. Once you’ve settled into the hotel and freshened up, you can head straight into the heart of the dazzling geological phenomenon on your doorstep. There’s a viewing platform that allows you to gaze over and into the vast canyon, that measures a mind-boggling 277 by 18 miles. We could also arrange for you to head out for an exclusive sunset helicopter ride over this natural wonder to take in its true scale.

Your next and final destination in Arizona is Flagstaff, a charming city surrounded by mountains, desert and pine forests and a popular stopover on Route 66. The drive takes about an hour and a half, leaving you plenty of time to explore the centre of town. On arrival, check into a cosy motel surrounded by forest and take a moment to rest and relax before heading for an explore. Flagstaff is known for its lively live music scene, as well as its selection of interesting and well-curated museums.

Today you’ll be switching gears a tad, swapping the calm of the countryside for the bright lights of Las Vegas. That’s right – after a four-hour journey through the arid Nevada desert you’ll arrive in the city of entertainment, exuberance and endless gambling. Along the way we recommend making a stop at the quirky town of Seligman, home to the longest surviving section of the original Route 66. Further along is Hoover Dam, a huge Art Deco dam in the Black Canyon of the Colorado River. On arrival in Las Vegas, check in for two nights in a glamorous new hotel on the Strip, just a few minutes' walk from iconic Bellagio fountains. The rest of today is yours to play with. We recommend turning to our handy Dossier to find a spot in the centre for an evening drink. Make sure to pause at the Bellagio to watch the mesmerising water display, which takes place regularly throughout the day.

Launched by a genius gangster, Las Vegas is arguably the only city in the world entirely built on illusion. And it’s easy enough to get caught up in the game. After a morning spent enjoying the swimming pool or shopping in one of the many malls, head out for a long walk down the Strip, passing from one themed hotel-casino to another and observing the bustling ballet of an ever more eccentric crowd. This evening, let yourself be enthralled in the ambient frenzy of the old Downtown or head to one of the city’s many luxurious starred restaurants for some high-end dining. Our team can also arrange for you round off your night watching the ‘O’ by Cirque du Soleil show at Bellagio.

As the casinos and neon lights of Vegas get smaller and smaller in the rearview mirror, a new landscape opens up in front of you: the dusty golden plains of the Mojave Desert. Your next destination, and final stop on this great American road trip, is none other than Los Angeles, a city of movie legends, timeless tales and year-round sunshine. We recommend making a few iconic Route 66 stops along the way: there’s the ghost town of Calico, an old West mining hub, and Barstow, which is full of classic diners and gas stations. On arrival in LA, check in for three nights in your final accommodation: a sleek and super trendy hotel in the heart of Hollywood.

You did it! After 19 days and 2,250 miles on the road, the time has come to put your feet up and soak in the seriously rewarding feeling of traversing North America’s most iconic highway. You have the next two days to experience the delights of LA life: laze on the beach (there are over a hundred of them), shop ‘til you drop in Beverly Hills, soak in the city skyline from Griffith Park, dine in celebrity-favourite spots and hike in the hills beneath the world-famous Hollywood sign. You’ll also have the opportunity to head out on a bike ride through Venice Beach and Santa Monica in the company of a clued-up local guide. The ride begins on Abbot Kinney, Venice Beach's fanciest street, with its designer boutiques and concept stores, as well as the Google and Snapchat offices. The district also owes its fame to its network of beautiful canals lined with architecturally-varied houses. Continue on to the beachside boardwalk to check out the local bodybuilders, surfers and skaters living a life of fun under the Golden State sun. Round off your visit with a tour of Santa Monica, a coastal city west of downtown LA known for its idyllic white-sand beaches, mythical amusement park and charming seaside resort feel. We could also arrange for you to send a few hours discovering the wonderful Universal Studios.