Route 66 Holiday Santa Monica to Chicago

Route 66 Holiday Santa Monica to Chicago

Enjoy this Route 66 holiday in reverse, start in Santa Monica and end in Chicago taking in old and authentic buildings, shops, cafes and motels. You really will feel as if you have stepped back in time

Duration: 14 Nights
Quote CHH1286

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Itinerary at a glance:

  • 2 nights Santa Monica
  • 2 nights Las Vegas
  • 2 nights Flagstaff
  • 2 nights Albuquerque
  • 1 night Amarillo
  • 1 night Oklahoma
  • 1 night Springfield
  • 1 night St Louis
  • 2 nights Chicago
We can tailor all hotels and durations to suit your requirements
Route 66 Holiday Santa Monica to Chicago

Sample Itinerary of Route 66 Holiday Santa Monica to Chicago

2 Nights Santa Monica
Your iconic Route 66 journey starts in Santa Monica, staying at the Gateway Hotel Santa Monica, where you can enjoy the classic California sunshine, the amazing Santa Monica Pier and Pacific Park – with amusement park rides like the Pacific Wheel. Santa Monica is a quaint coastal Californian town to walk around or spend your day on the amazing Santa Monica beach with its golden sands a beautifully blue Pacific Ocean. Route 66 actually finishes on Santa Monica Pier so be sure to get a picture the iconic sign as you'll actually be driving the iconic Route 66 in reverse!

2 Nights Las Vegas
Setting off along Route 66 your next destination will be Las Vegas, however there are some amazing stops to make along the way. Located along Route 66 between Santa Monica and Las Vegas is the first ever McDonald's restaurant- even if you're not into the fast-food chain, this is certainly a historic and quirky point to pull over at. Another iconic point to stop at is Elmer’s Bottle Tree Ranch - a eccentric art installation, and a great place to stretch your legs. Barstow is the last big town along Route 66 before Las Vegas, and a great place to see some of Route 66’s history including old iconic Route 66 motels and museums. Roy’s Café in Barstow is also an ideal place for a bite to eat before your final stretch towards Las Vegas. Driving on this stretch of Route 66 will also take you past abandoned motels like Roy’s Motel and Cafe that were once iconic landmarks along the historic Route 66- these are now great photo opportunities and offer a glimpse into the past. Once in Las Vegas you will be staying at the New York New York Las Vegas Hotel & Casino – a great Las Vegas hotel set right on the Las Vegas Strip. Home to the Mad Apple by Cirque du Soleil show and Las Vegas is most famous roller coaster, the Big Apple coaster, the New York New York is an amazing hotel to stay at to whilst in Las Vegas.

2 Nights Flagstaff
Your next stop along Route 66 is Flagstaff at the Hilton Garden Inn, but before you get to Flagstaff there are many things to do along Route 66. For example, just outside of Las Vegas is the incredible Hoover Dam-where if you stand directly in the middle, you can be stood in both Nevada and Arizona at once! If you make a slight detour, you'll come to the abandoned goldmine town Nelson Ghost Town - this town is open for tours and is full of retro unrestored buildings, signs, and photos. Continuing with the history theme, further along Route 66 you will come to the town of Chloride - this is the oldest inhabited mining town in Arizona and worth taking a look around on your way to Flagstaff. Along what is called Historic Route 66 you'll also come to a general store, Hackberry General Store, where you can stop and grab some food and drink but also admire the quirky shop and its history. Before arriving in Flagstaff, you will come to the city of Williams - home to Route 66 Zipline and Route 66 Gas Station Museum, this is another great location to have a look around enjoy some more historic Route 66 memorabilia.

Whilst in Flagstaff you will be able to visit the stunning Grand Canyon National Park. There are many ways to get to the Grand Canyon including by air and by road, but a particularly enjoyable way to get there is by rail - the Grand Canyon Train has been taking visitors to the Grand Canyon since the 1900s. The train ride there is leisurely and very scenic and a great way to see the surrounding environment as well as the Grand Canyon.

2 Nights Albuquerque
The next destination on your Route 66 holiday is Albuquerque, where you will stay at Hotel Andaluz Albuquerque. Before you reach Albuquerque, there will be plenty of things to do and see along Route 66. Just outside flagstaff, you will come to Montezuma Castle National Monument - this is an important historic site within Arizona and dates back over 1000 years. If you're looking for a place to stop and stretch your legs, then a must-see desert town in Arizona is Sedona - surrounded by majestic red rock canyons and pine forests, Sedona is known for its beautiful and mysterious ways. After driving for a while along Route 66 you might find yourself getting a bit hungry, why not stop for an elegant bite to eat at The Turquoise Room inside La Posada Hotel. This restaurant is much more upmarket than the dining motels you might have been experiencing along Route 66, and perfect if you're craving some Arizona delicacies.

After you've crossed into New Mexico, you will come across the city of Gallup - the largest city between flagstaff and Albuquerque and it’s full of all the great Route 66 memorabilia and locations such as motels, diners and flashing neon signs. Gallup is a great place to stretch your legs and grab a bite to eat along the road. Another landmark, one you might not expect to find in the middle of the desert, is an ice cave, but The Ice Cave and Bandera Volcano offer an amazing journey into the volcano where you can see an ice cave thanks to low temperatures... This privately owned landmark is certainly worth the small entrance fee and an amazing stop along Route 66.

On your way into Albuquerque you will pass The Laguna Pueblo; an area that has been inhabited for nearly 1000 years and from the road you will be able to see the iconic whitewashed St. Joseph Church - so be sure to be on the lookout for this as you drive along Route 66 into Albuquerque. If you fancy getting off the road for a bit, and up into the skies, why not take a scenic hot air balloon ride up over the city for amazing panoramic views of the city and the surrounding New Mexico desert.

1 Night Amarillo
On your way to Amarillo, where will you stay at Staybridge Suites Amarillo, one of the first pit-stops you’ll want to make is the Singing Road- if you drive along the pavement over the grooves at exactly 45 mph, and you'll hear the familiar tune of “America the Beautiful”! Another pit-stop along Route 66 on the way to Amarillo is one that would be much appreciated by dessert lovers - Pie Town. Pie Town has been serving delicious homemade pies since the 1920s and it's a great place to stop for a bite to eat, and a look around the historic town. After more driving along Route 66 you'll come to Santa Rosa- home to an 80-foot deep blue hole, an Oasis in the desert. Another area where you can cool off as you head towards Amarillo is Ute Lake State Park in Logan – with many miles of shoreline this is a great place to take a break and admire one of the scenic views along Route 66. Soon after this you will reach the midpoint of Route 66 which is commemorated with MidPoint Café- a retro diner that is a great place to stop for a bite to eat and to reflect on the first half if your Route 66 journey. Once you reach Amarillo there are plenty of things to do in this Texan city, for example visit the botanical gardens or one of the many museums... or if you fancy a hike through the Texan Panhandle there is plenty of that too.

1 Night Oklahoma
On your journey from Oklahoma, where you will stay at the Hilton Garden Inn Oklahoma City Bricktown, one of the first landmarks you will come across is the Leaning Tower of Texas - you can see this from your car and it really is a great photo opportunity! This stretch of the journey is quite remote and there are a few abandoned towns you could drive through, like Jericho, but an iconic Route 66 landmark you must see are U Drop Inn and U Drop Cafe in Shamrock. This building is so famous it's actually featured in the Disney movie Cars, and Elvis Presley actually stopped here for some food when he travelled on Route 66! Another great stop along this leg of your Route 66 road trip is Oklahoma Route 66 Museum in Clinton - some people argue this is the best Route 66 museum and it is a great opportunity to learn about the road you have now driven over half of. Once in Oklahoma City Bricktown, you will be amongst she chic and trendy restaurants, cafes, nightlife and plenty of things to do.

1 Night Springfield
On your way to Springfield, where you’ll stay at the DoubleTree by Hilton Hotel, you’ll cross into Kansas. One of the pit-stops we highly recommend making is in the remote town of Riverton. In Riverton you'll come across many authentic Route 66 places such as the old Riverton Store - a convenience store frozen in time, where you will be able to pick up some amazing souvenirs. Once in Springfield be sure to check out the motel Elvis Presley stayed at: Rail Haven Motel, and for those who can't get enough of the historic cars on this Route 66 road trip then Springfield is also home to Route 66 Car Museum.

1 Night St Louis
The second last leg of your road trip along Route 66 will take you through Missouri to St Louis, where you will stay at Hampton Inn St. Louis-Downtown (At the Gateway Arch). On your way to St Louis, you’ll come to a small town in the The Ozarks called Conway – this is a quaint, historic town in The Ozarks and worth having a look around. One of the next pit-stops worth making is at the small town of Devil's Elbow, within the Missouri Ozarks, Devil’s Elbow is an iconic Route 66 town home to scenic lookouts and small shops and diners. Before arriving in St Louis, you’ll drive through a few towns, some abandoned, that are home to historic and authentic Route 66 motels that are worth stopping at even just for a picture! St Louis itself is a vibrant city full of things do for example visiting the Gateway Arch and Busch Stadium. Thrill seekers might want visit Six Flags St. Louis and ride one of the iconic six flag roller coasters! Another fun to do whilst in St Louis is visit St. Louis Union Station, once one of the busiest railway stations in the Midwest, it is now home to the St Louis aquarium, the 200-foot St. Louis Wheel, a carousel, an 18-hole mini-golf course and more!

2 Nights Chicago
The final part of your Route 66 road trip will take you into Chicago, where you will stay at Hotel Felix Chicago. As you head towards Chicago, one of the first pit-stops you might want to make is at the infamous hangouts of Al Capone: The Luna Café. The Luna Café is not particularly fancy, but that's part of its authentic Route 66 feel. Now that you have made it this far along your Route 66 journey, you can pay a visit to The Shrine of Our Lady of the Highways and thank her for your safe passage on your Route 66 road trip, as travellers of this highway have been doing since the 1950s.

Remember way back when you took the photo of the Route 66 Ends Here sign on the Santa Monica Pier, will now that you've reached Chicago you can take a picture of the Route 66 Starts Here sign at the corner of S Michigan Avenue and E Adams Street. Yes you may have done your Route 66 road trip backwards, but you will have loved it all the same! Whilst in Chicago, be sure to also checkout some famous Chicago landmarks such as the sculpture Cloud Gate or the Ice Cream Museum!

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