Route 66 From Chicago to California

Route 66 From Chicago to California

Stretching from Chicago's skyscrapers to Santa Monica's pier, take this 18 day/17 night itinerary Route 66 holiday on a nostalgic journey through the heart of America

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Itinerary at a glance:

  • Chicago IL 2 nights
  • St Louis MO 2 nights
  • Springfield MO 1 night
  • Oklahoma OK 1 nights
  • Shamrock TX 1 nights
  • Santa Rosa NM 1 night
  • Gallup NM 1 night
  • Williams AZ 2 nights
  • Las Vegas NV 3 nights
  • Needles CA 1 night
  • Santa Monica CA 2 nights
We can tailor all hotels and durations to suit your requirements
Route 66 From Chicago to California

Sample Itinerary of Route 66 From Chicago to California

2 Nights Chicago
The first location on your Route 66 road trip, and where you will fly into is, Chicago – staying at the Swissotel Chicago. Whilst in Chicago be sure to get a picture with the iconic Route 66 Starts Here sign at the corner of S Michigan Avenue and E Adams Street. Also, in Chicago be sure to visit some of the city’s most iconic landmarks including the Cloud Gate sculpture and Millennium Park. Your Route 66 journey will begin as you leave Chicago and head towards your final destination of Santa Monica California, but before reaching Santa Monica there will be many stop to see and make along Route 66.

2 Nights St Louis
After the first leg of the journey along Route 66 you will stop for the night in St. Louis, staying at the Holiday Inn St Louis South West. Before you arrive in St Louis though there are plenty of stops to make along the way. One of the first stops you might like to make as you leave Chicago and head towards St. Louis along Route 66 is at Atlanta, Illinois. Atlanta, Illinois is home to the hidden gem that is the Route 66 Arcade Museum- the museum is full of old arcade games that you can still use today! Another landmark on this leg of the journey is Ambler's Texaco Gas Station in Dwight - this was a gas station in operation for 66 years, one of the longest operating ones on Route 66, that is now a visitor centre. The visitor centre will give you interesting information on the Route 66 road trip you're about to embark on. St. Louis is also a great city in the Midwest with many things to do such as visiting the iconic Gateway Arch, the newly renovated St. Louis Union Station which is now home to a variety of attractions including an aquarium, and much more!

1 Night Springfield
This stretch of the journey to Springfield, where you will stay at the Best Western Route 66 Rail Haven, is really a trip back in time on Route 66 and takes you through some abandoned towns and past Authentic Route 66 motels - for example you will see the Wagon Wheel Motel which has been around for over 60 years and housing guests travelling along Route 66. Though you might not be staying the night in these authentic Route 66 motels, they're still great to have a look at, take some pictures and enjoy the history surrounding the Route 66 motels. One town along this leg of the journey that you might want to stop up is Cuba - this is a small town full of amazing murals that's a great place to stretch your legs and admire the artwork. Once you arrive in Springfield, be sure to check-out some more of the classic Route 66 motels and their neon signage in this small town – especially Rail Haven Motel where Elvis Presley stayed on his Route 66 road trip!

1 Night Oklahoma
On your way to Oklahoma you will pass through some of Route 66’s more modern, but still iconic, history. Route 66 has been made famous in the last few years again by the Disney movie Cars, along this stretch of the road trip you will pass through the quaint town of Galena. Galena is famously where the character “Tow Mater” in Disney’s Cars is from, as he was based on an old rusty tow truck that sat in the town. In the town you can see characters from the movie Cars all along Main Street - this is great fun even for those who aren't fans of the movie as it gives you an idea of what type of cars and buildings would have been along the historic Route 66. Once you arrive in Oklahoma for the night there are plenty of things to do and see, for example why not visit the National Cowboy and Western Heritage Museum or even the Oklahoma Zoo.

1 Night Shamrock
On this next leg of the Route 66 road trip you'll leave Oklahoma City and head for Shamrock Texas, where you will stay at the Best Western Plus Shamrock Inn and Suites. Along the way you will find many places to stop including, Elk City or the home of the National Route 66 Museum. This is certainly a great place to stretch your legs and have a look around on your way to Shamrock. Shamrock is famous for its Route 66 building the U-Drop Inn/Conoco Tower - This is an iconic piece of Route 66 history and architecture, and though Shamrock is a small town it is a great place to spend the night on your Route 66 road trip.

1 Night Santa Rosa
On your way to Santa Rosa, where you will stay at the Hampton Inn Santa Rosa, the journey will begin quite remote, but some stop-worthy locations are the Leaning Tower of Texas and The Largest Cross in the Western Hemisphere (190ft!). A motel worth pulling over at and having a look around is Bug Ranch with its quirky art installation. The next big town you’ll come across is Amarillo where you can stop for a bite to eat at the Big Texan Restaurant - this restaurant serves classic Texan steaks, cowboy style. If you’re feeling up to it, you could also try their 72 challenge: you have to finish one 72 oz. steak, one baked potato, one side salad, one shrimp cocktail, and one dinner roll, in one hour or less. If you finish, the meal is free, and you get a tee-shirt. If you don’t, you owe them $72. After Amarillo you’ll carry on driving further down Route 66 into Texas to Santa Rosa, where after checking-in you can cool off in the infamous Santa Rosa Blue Hole- an oasis in the Texan desert!

1 Night Gallup
Your next destination for the night along Route 66 is Gallup New Mexico, where you will stay at the Historic El Rancho Hotel. Though, along the way you will come across the city of Albuquerque - whilst in Albuquerque why not checkout the Historic Nob Hill area - this part of the city is glowing with neon lights, and modern dining options, and offers a unique and authentic Route 66 experience. If you don't fancy having anything to eat in Albuquerque, then a bit further along Route 66 you'll come across Wow Diner: a truly authentic American diner that will make you feel as if you stepped back in time! Try one of their amazing milkshakes or simply order a beer! As you carry on towards Gallup you will drive past the Route 66 Casino Hotel – why not stop in for a game or two?! Another Route 66 landmark to visit long this leg of the road trip is Bluewater Lake State Park - is a great place to stretch your legs and take in the surrounding views of the glistening lake and the Zuni Mountains. Once in Gallup, there are plenty of things to do from floating through the Red Rock Canyons in a hot air balloon to experiencing the rich Native American culture in the small New Mexican town.

2 Nights Williams
Your Route 66 road trip will next take you to the town of Williams Arizona, where you’ll stay at the Grand Canyon Railway & Hotel - this hotel is a real treat along Route 66 as it has been modelled after an old-world train station from Arizona. It is also ideally located for those who want to explore the Grand Canyon via train - an excellent and extremly scenic way to see the Grand Canyon National Park. Along this leg of Route 66 you'll find more of the routes iconic motels including the Wigwam Village Motel #6 - this is the perfect photo spot from those who love vintage American cars and Route 66’s vibrant history. Another scenic activity is visiting Petrified Forest National Park, parts of Historic Route 66 also go straight through the park, as within the park you will find ancient trees that have been turned into gemstones, ruins from ancient societies, beautifully coloured desert sand and much more!

Along this leg of Route 66 you'll also be treated to a lot of natural history including visiting the amazing Meteor Crater- the world's best preserved meteor impacts site, and also the opportunity to see a 700,000-year-old lava tube cave! You will also drive through the city of Flagstaff, a vibrant and historic city full of many shops and restaurants to visit if you fancy having a walk around. Soon after Flagstaff you'll arrive in Williams, where you can check- in to your hotel. Alongside visiting the Grand Canyon National Park in Williams there are also more adventure-style activities such as the Route 66 Zipline.

3 Nights Las Vegas
The next leg of your Route 66 road trip will end in fabulous Las Vegas where you stay at The LINQ Hotel and Casino. The LINQ is a great hotel right on The Strip and also next to the LINQ Promenade – an area full of plenty of attractions, shopping, and restaurants to visit. Though on your way to Las Vegas there will also be loads of places to stop at and see. Just outside of Williams you'll come to Angel & Vilma Delgadillo's Original Route 66 Gift Shop - this is a must stop location, where you can pick up some souvenirs, but also get a feel for some of the original locations along this historic road. Next up is the Arizona Route 66 Museum where, if you're loving driving Route 66, you can take a look around and learn about the history of the infamous cross-country road. The museum is full of old cars, relics, and more for a fascinating insight into Route 66.

Just before entering Las Vegas, you'll come to Hoover Dam - Hoover Dam is certainly worth stopping at and taking a look around, and if you stand directly in the middle of Hoover Dam you will be in both Nevada and Arizona at once! Once in Las Vegas there is so much to do in the see from walking down the Las Vegas Strip and visiting many of the hotels for example Caesars Palace, Bellagio, The Venetian and more! From spending time in the Casinos, enjoying fantastic food, shopping in the amazing malls, or even playing a round of golf there is so much to do and see in Las Vegas!

1 Night Needles
After Las Vegas, you will need to re-join Route 66 and to do this you will head to the town of Needles California where you will stay at the Best Western Colorado River Inn. Driving to Needles is not too long, so it can easily be done in one hit. When you arrive in Needles you can spend some much-needed downtime relaxing by Lake Havasu. If you feel like getting out and about nature then why not walk the trail of Picture Canyon - aptly named, picture Canyon is a beautiful and picturesque walk through the Canyon. As you leave Needles and head towards Santa Monica be sure to pass by the iconic Needles Borax Wagon for a great photo opportunity!

3 Nights Santa Monica
The final leg of your Route 66 road trip will come to an end in Santa Monica where you will stay at the Gateway Hotel Santa Monica. Though your Route 66 road trip is not over yet and there is plenty to see on this final leg of the journey. One iconic, historic landmark is Roy's Motel and Café - thanks to its large neon sign it is reminiscent of the old motels along Route 66 and certainly worth pulling over at. Ludlow Motel and Café is another option slightly further down the road where you can grab a bite to eat and stretch your legs as you look around the authentic Route 66 motel. Another stop worthy location along this leg of Route 66 is the Wigwam Motel - the Wigwam Motels were famous across the country and there are only three remaining today. Another great location to pullover is The Original McDonald's building which is now been turned into a museum.

Once you've arrived in Santa Monica and checked in, be sure to visit the iconic Route 66 Ends Here sign located on Santa Monica Pier. Whilst on the pier why not ride on one of the great Pacific Park amusement rides like the Pacific Wheel, or maybe spend the day relaxing on the golden sand beach of Santa Monica. Santa Monica is just outside the city of Los Angeles so visiting LA for the day couldn't be easier: you could drive down Rodeo Drive, visit the Hollywood Sign, or even Universal Studios Hollywood if you fancied it!

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