Route 66 Chicago to LA Car Tour and Rental

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DSCN9709CLICK FOR 1,000 PICTURES FROM A ROUTE 66 CHICAGO TO LA CLASSIC CAR TOUR – now tours are with new Mustangs

2nd Set of Pictures

 

Route 66 new Muscle Car Rental and Tours for you or your group. We arrange it all,  just like our motorcycle tours. Contact us To join a current car tour we have planned, or to book a custom tour for your group.  Schedule Below.

Ride the Pacific Coast Highway in a new late model Muscle Car, or cruise route 66 in a car rental.  We rent the cars on guided tours along the California Coast Pacific Coast Highway. Or drive RT 66 in a classic car rental.   Ride Free Tours leads the group in a  car.  All you have to do is have fun.  We take care of the car rental, route, hotels,  any worries, and anything that happens along the way.

Self Guided Car Tour Option: car, route, attractions,hotels, gps
CONTACT for Self Drive packages and rates.  Self Guided Rt 66 Car  Pricing

RENT a new Muscle Car or Exotic BY YOURSELF Option  with no tour, no support truck, no guide

Route 66 Chicago to LA Guided Car Tour and Rental – 15 days
Drive Chicago to LA in a car on Route 66 the Mother Road of America.  Chicago, Route 66, The Grand Canyon, Las Vegas, Los Angeles
A once in a life time journey and opportunity not many have ever had the chance to do since the 1950’s!

9 Day 8 Night – Route 66 Albuquerque/ Santa Fe to Los Angeles  Guided Tour
This trip across America is the same as the Traditional Chicago to LA Route 66
guided tour, but we drive from Albuquerque / Santa Fe  to Los Angeles on Route 66.

9 day 8 night Albuquerque/ Santa Fe to Los Angeles
$1525  – Per person with 4 people, 1 car, 2 rooms
$2033  – Per person with 3 people, 1 car, 2 rooms
$2999  – Per person with 2 people, 1 car, 1 room

15 Day 14 Night Chicago to LA Car Tour and Rental – Guided Tour with Support
  • 14  Nights of hotel starting the first night in Chicago and arrival day to LA
  • 1 room included – option to add 2nd room if want – $200×14= $2800 for extra room
  • 13 Days of rental and one way fee included
  • Included: tour guide in car, taxes, full damage waiver, 1 million supplemental liability waiver, one way fee for 1 car
  • Not Included: gas, food, extra, entrance fees, 2nd hotel room if want

CLICK FOR PICTURES FROM A ROUTE 66 CHICAGO TO LA CAR TOUR

ADD $605 ONE WAY FEE PER VEHICLE TO PRICING BELOW

Cost 15 Day 14 night Guided Car Tour Chicago to LA
$2507  – Per person with 4 people, 1 car, 1 room
$3343  – Per person with 3 people, 1 car, 1 room
$5014    – Per person with 2 people, 1 car, 1 room
$10,015  – Per person with 1 person, 1 car, 1 room

Cost 16 Day 15 night Guided Car Tour Chicago to LA
$2696  – Per person with 4 people, 1 car, 1 room
$3595  – Per person with 3 people, 1 car, 1 room
$5385  – Per person with 2 people, 1 car, 1 room
$10,770  – Per person with 1 person, 1 car, 1 room

Cost 17 Day 16 night Guided Car Tour Chicago to LA
$2885  – Per person with 4 people, 1 car, 1 room
$3847  – Per person with 3 people, 1 car, 1 room
$5763  – Per person with 2 people, 1 car, 1 room
$11,525 – Per person with 1 person, 1 car, 1 room

Cost 19 Day 18 night Guided Car Tour Chicago to LA
$3259  – Per person with 4 people, 1 car, 1 room
$4345  – Per person with 3 people, 1 car, 1 room
$6518  – Per person with 2 people, 1 car, 1 room
$13,035 – Per person with 1 person, 1 car, 1 room

Self Guided  Car Tour Option: car, route, attractions,hotels, gps
Self Guided Rt 66 Car  Pricing Chicago to LA in new Mustang Convertible ( click here )
CONTACT for Self Drive packages and rates   Self Guided Rt 66 Chicago to LA Car  Pricing

# The 16 Day Tour takes the 2 longest days of the 15 day tour, and cuts them in half.  I highly recommend.
The 17 Day really makes a relaxed trip, and adds a layover or mountain day in Santa Fe.  The Ultimate.  Wil’s choice.

2017 Chicago to LA Car Tour – Start Dates
March 5 – April 5 – May 5  – May 19  –June 9 –July 7 – July 30 –Aug 4  –  Aug 15- Sept 3  –Oct 2  – Nov 2
2018 Chicago to LA Car Tour – Start Dates
March 5 – April 5 – May 5  – May 19  –June 9 –July 7 – July 30 –Aug 4  –  Aug 15- Sept 3  –Oct 2  – Nov 2

Contact Us HERE

But what really makes a Ride Free Adventure is The Team, check out our crew.  Our love for being on the road on an adventure with great people from around the world is what it is all about for us.

Or for a shorter Route 66 trip, you can join the portion from Albuquerque to LA on Route 66.  This is a 10 Day Tour.

We stay at the top of the Grand Canyon for the sunset and sunrise, unlike most tours who only stay only at the bottom.  We also spend a whole day at the Grand Canyon the next day giving time for a helicopter ride or donkey ride, then ride to the bottom so we have more time on an amazing part of Route 66 the next day.  We also get to Vegas early so you have a full afternoon and relaxed evening in Las Vegas.

16 Day Route – Route 66 Chicago to LA Car Tour

Day 1–Arrive in Chicago
We meet after lunchtime at the hotel and talk about our upcoming adventure on the Mother Road of America, Route 66 Chicago to LA.
We also do an orientation with the classic cars to familiarize ourselves with the upcoming adventure on Route 66 in cars like Mustang Convertibles.
Then we go out for dinner after checking out the beginning of Route 66 in downtown Chicago to discuss our big adventure!


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Day 2–Chicago to Springfield, Illinois-185 miles

Let’s get in our cars  and drive on Route 66!
We settle into our car rentals , and aim for California. This is our first night on the road.
See icons such as the “Gemini Giant”, “Rocket Man”, “Old Log Cabin”, the old “Marathon Oil Station”. We also stop at the RT 66 Museum in Joliet.

That afternoon we arrive to Springfield and stay at a nice local hotel in historic downtown where we can visit the amazing Lincoln Museum if we have time before having dinner at a local restaurant and celebrate our first night on the road.


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Day 3– Springfield, MO  to Saint Louis – 129 miles

Riding Rt 66. Exploring St. Louis. The Gateway Arch welcomes travelers heading East or West.  Maybe a blues bar tonight?

Before we get to Saint Louis, we drive out cars with the top down to the historic Chain of Rocks Bridge.  We will walk out on the old bridge!


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Day 4–St Louis to Lebanon, MO – 189 miles

Riding Rt 66 through neat little towns. We have really fallen into sync with our rides now.. Americana.   How about some great American BBQ?  We get a picture with the worlds largest Rocking Chair.  Devils Elbow is amazing.   This is small town America.  At a glance it does not seem like much has changed.  We hang out with the locals tonight and relax under the stars under some neon light of a vintage Rt 66 Motel in the countryside.


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Day 5– Lebanon to Tulsa, OK  – 264 miles
Great section of RT 66 with all the Googie Architecture. A really great ride. Great old diners.  A really nice driving day.   This is one of the longest days, but a great day.
This is RT 66!    We stop and meet some very interesting people along the ride today, and ride over a famous RT 66 Bridge in our cars.   Then we go stop at a great little motorcycle museum along the way that has a great history of Rt 66.


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Day 6– Tulsa, OK to Clinton, OK  – 221 miles – 5hr 30mins driving

Today is a really nice cruise through the countryside.  So many great little signs and remnants of the hay days of this great road to see.  We end the day with the Oklahoma Route 66 Museum where we can travel in time back to the glory days of Rt 66.


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Day 7– Clinton  to Amarillo, Texas –206  miles

In the morning after a short ride we visit the Elk Cit Rt 66 Museum.  I could spend a day at this one.  It is absolutely amazing.  The farming history, Wild West History, and every aspect of old America.  Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?   Everything is bigger in Texas.   You will know you are on old Rt 66 today.  It will feel like a throwback to what it was like to travel Rt 66 on the road in years past.


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Day 8–Amarillo to Santa Fe, New Mexico –  375 miles

Cadillac Ranch is a Route 66 stop we must do.  Who has ever spray painted a vintage Cadillac on Rt 66 before?  Let me ask you again in the future… Midpoint of Rt 66 at the Midpoint Cafe!   Amazing day of vintage hotels and neon signs like The Blue Swallow and others.   Welcome to Santa Fe. Art galleries, great restaurants, great walking around…. This is really an amazing Southwest city to spend time in.  We discover the rich history and culture of Santa Fe after a big day riding Route 66 in our cars.

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Day 9–Santa Fe  to Gallup – 218  miles 
We follow the Route 66 path, and end at the little town of Gallup, at the Rancho Hotel.

The historic El Rancho Hotel and Motel has hosted a numerous array of movie stars including John Wayne, Ronald Reagan, Humphrey Bogart, Spencer Tracy, Katharine Hepburn, Joan Crawford, Kirk Douglas, Doris Day, Gregory Peck, and Burt Lancaster. The rugged terrain surrounding Gallup was popular with Hollywood film makers during the 1940’s and 1950’s for the on-location shooting of Westerns. Actors and film crews would stay at the hotel during filming.


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Day 10–Gallup to Grand Canyon National Park South Rim –286 miles
First, we will stand on a corner in Winslow, Arizona.  We will get pictures with you and your car on a corner in Winslow, Arizona.

Next we drive down the main drag on Rt 66 in our Convertibles with the top down through Flagstaff. Then, we stay on top of the Canyon and watch the sunset the first night. The Grand Canyon. “That’s one big hole!”, enough said.  Seeing the sun set over the Grand canyon is one of the things that everyone should see once in a lifetime.  We have dinner right on the rim of the Canyon.  At night, we can walk back over to the rim under the stars.


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Day 11–Grand Canyon South Rim to Williams, AZ – 60 miles – 1hr – Almost Full Day At Grand Canyon! – Or go for an amazing drive.
What is different about Ride Free Chicago to LA Route:  We stay at the top of the Grand Canyon for the sunset, unlike most tours who only stay at the bottom.  We also spend a whole day at the Grand Canyon the next day, then ride to the bottom so we have more time on an amazing part of Route 66 the next day.
For those that want to ride more, we have an amazing ride set up for the day.

Who is up for a helicopter ride across the canyon after watching the sunrise?

Hike down a trail the next am. into the Grand Canyon. Ride the donkeys down the trail into the canyon? Just relax enjoy the sites and history.

Check out the Watchtower. Lots of great things to see. We get a full day in The Grand Canyon. When we are done here, we start heading back down the mountain and stop if you want for a helicopter or plane ride into the Canyon. Or maybe an old train ride? We then work our way down the hill after an amazing day to Williams for dinner and a night on the little town. Or sleep. Ready to hit the road the next am for an amazing day.


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Day 12–Williams to Laughlin, NV – 230 miles – 4hr 47min

An amazing Old RT 66 day! All the RT 66 shopping you could think of. We will be on the forgotten RT 66 a lot of the day. Grand Canyon Caverns, Peach Springs, Kingman…Towards the end of the day we will work our way on an incredible slow winding road to the old mining town of Oatman. Wild burros, real old 49er gold miners with real Colt 45s on their hips to protect their gold. A forgotten town. Not much has changed here the past 100 years. It is almost unbelievable that is winding mountain road was the main East West road until 1953 when Rt 66 was re routed. Time has held still since then in Oatman.

Laughlin is a little Gambling town on the way to Vegas on the Colorado River. Let’s get you ready for the Big Time tomorrow.
Ribeye Steak tonight!


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Day 13–Laughlin, NV to Las Vegas, NV –99 miles  – 1hr 38min – Almost Full Day in Vegas!

An early morning ride out beats the heat, and gets us to Vegas early for a full day….  Plenty of time relax in your Vegas room and get cleaned up before hitting the Vegas Strip. Of course we get a picture in from of the famous Las Vegas sign when we ride in town down the strip in our cars.
Or, instead of just Vegas lounging, we have some great rides out from Vegas if you want some more cruising our Mustangs in Las Vegas.  Like Red Rock Canyon and some other stops.

But first the Hoover Dam!
Vegas – Pools, shows, fun. We will have most of the day to explore Vegas, and the whole relaxed evening.


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Day 14–Las Vegas, NV to Victorville, CA –190 miles

( or we can do Big Bear Lake Option 296 miles – 5hr 24min )

We follow the original path of Old Route 66 where we  explore the amazing Mojave desert.  If we do the Big Bear Option we climb into the cool Alpine town of Big Bear Lake at the end of the day.

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Day 15–Victorville to Santa Monica Pier! –100 miles. plus exploring and Malibu Coast Ride!

( Big Bear Option 1   –  152 miles – 3hr 26min )

Over the famous Cajon Pass, then we drop into LA, freeways, civilization. We make it through all the way to the end. The Santa Monica Pier. We can go to Hollywood Blvd today, or we can explore the refreshing California Coast. Malibu, Venice Beach, Santa Monica… let’s keep the Ride Free tradition of ending the tour by putting our feet into the cold Pacific!

We turn the bikes in at the end of the day.

Let’s celebrate tonight!

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Day 16–Los Angeles Departure

We say our goodbyes, and plan for our next adventure. There is so much more to see in the USA in the future.

A shuttle will take you to the LAX.


OPTION 1:  15 DAY 14 NIGHT – Traditional Route 66 Car  Tour

Day 1–Arrive in Chicago
We meet after lunchtime at the hotel and talk about our upcoming adventure on the Mother Road of America, Route 66 Chicago to LA.
We also do an orientation with the cars to familiarize ourselves with the upcoming adventure on Route 66 in cars like new Mustang Convertibles.
Then we go out for dinner after checking out the beginning of Route 66 in downtown Chicago to discuss our big adventure!


Day 2–Chicago to Springfield-185 miles


Let’s get in our cars  and drive on Route 66!
We settle into our car rentals , and aim for California. This is our first night on the road.
See icons such as the “Gemini Giant”, “Rocket Man”, “Old Log Cabin”, the old “Marathon Oil Station”. We also stop at the RT 66 Museum in Joliet.

That afternoon we arrive to Springfield and stay at a nice local hotel in historic downtown where we can visit the amazing Lincoln Museum before having dinner at a local restaurant and celebrate our first night on the road.


Day 3–Bloomington to Saint Loius, MO 175miles


Riding Rt 66. Exploring St. Louis. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Before we get to Saint Louis, we drive our cars with the top down to the historic Chain of Rocks Bridge.  We will walk out on the old bridge!


Day 4 – St Louis to Springfield, MO – 216 miles

Riding Rt 66 through neat little towns. We have really fallen into sync with our rides now.. Americana. Devils Elbow is amazing.


Day 5–Springfield to Oklahoma City –285 miles
Great section of RT 66 with all the Googie Architecture. A really great ride. Great old diners.
This is RT 66!


Day 6–Oklahoma City to Amarillo, Texas –259 miles

Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?   Everything is bigger in Texas.   You will know you are on old Rt 66 today.  It will feel like a throwback to what it was like to travel Rt 66 on the road in years past.


Day 7–Amarillo to Santa Fe, New Mexico –279 miles

Cadillac Ranch is a Route 66 stop we must do.  Who has ever spray painted a vintage Cadillac on Rt 66 before?  Let me ask you again in the future…   Welcome to Santa Fe. Art galleries, great restaurants, great walking around…. This is really an amazing Southwest city to spend time in.  We discover the rich history and culture of Santa Fe after a big day riding Route 66 in our cars.


DAY 8–Santa Fe  to Gallup –191 miles plus excursions
We follow the Route 66 path, and end at the little town of Gallup, at the Rancho Hotel.

The historic El Rancho Hotel and Motel has hosted a numerous array of movie stars including John Wayne, Ronald Reagan, Humphrey Bogart, Spencer Tracy, Katharine Hepburn, Joan Crawford, Kirk Douglas, Doris Day, Gregory Peck, and Burt Lancaster. The rugged terrain surrounding Gallup was popular with Hollywood film makers during the 1940’s and 1950’s for the on-location shooting of Westerns. Actors and film crews would stay at the hotel during filming.


Day 9–Gallup to Grand Canyon National Park South Rim –283 miles
First, we will stand on a corner in Winslow, Arizona.  We will get pictures with you on a corner in Winslow, Arizona.

Next we drive down the main drag on Rt 66 in our vintage Mustang Convertibles with the top down through Flagstaff. Then, we stay on top of the Canyon and watch the sunset the first night. The Grand Canyon. “That’s one big hole!”, enough said.  Seeing the sun set over the Grand canyon is one of the things that everyone should see once in a lifetime.  We have dinner right on the rim of the Canyon.  At night, we can walk back over to the rim under the stars.


Day 10–Grand Canyon South Rim to Williams, AZ –51 miles – Almost Full Day At Grand Canyon! – Or go for an amazing drive.
What is different about Ride Free Chicago to LA Route:  We stay at the top of the Grand Canyon for the sunset, unlike most tours who only stay at the bottom.  We also spend a whole day at the Grand Canyon the next day, then ride to the bottom so we have more time on an amazing part of Route 66 the next day.
For those that want to ride more, we have an amazing ride set up for the day.

Who is up for a helicopter ride across the canyon after watching the sunrise?

Hike down a trail the next am. into the Grand Canyon. Ride the donkeys down the trail into the canyon? Just relax enjoy the sites and history.

Check out the Watchtower. Lots of great things to see. We get a full day in The Grand Canyon. When we are done here, we start heading back down the mountain and stop if you want for a helicopter or plane ride into the Canyon. Or maybe an old train ride? We then work our way down the hill after an amazing day to Williams for dinner and a night on the little town. Or sleep. Ready to hit the road the next am for an amazing day.


Day 11–Williams to Laughlin, NV –190 miles

An amazing Old RT 66 day! All the RT 66 shopping you could think of. We will be on the forgotten RT 66 a lot of the day. Grand Canyon Caverns, Peach Springs, Kingman…Towards the end of the day we will work our way on an incredible slow winding road to the old mining town of Oatman. Wild burros, real old 49er gold miners with real Colt 45s on their hips to protect their gold. A forgotten town. Not much has changed here the past 100 years. It is almost unbelievable that is winding mountain road was the main East West road until 1953 when Rt 66 was re routed. Time has held still since then in Oatman.

Laughlin is a little Gambling town on the way to Vegas on the Colorado River. Let’s get you ready for the Big Time tomorrow.
Ribeye Steak tonight!


Day 12 – Laughlin, NV to Las Vegas, NV – 97 miles – Almost Full Day in Vegas!

An early morning ride out beats the heat, and gets us to Vegas early for a full day….  Plenty of time relax in your Vegas room and get cleaned up before hitting the Vegas Strip. Of course we get a picture in from of the famous Las Vegas sign when we ride in town down the strip on our Classic Cars.
Or, instead of just Vegas lounging, we have some great rides out from Vegas if you want some more cruising our Mustangs in Las Vegas.  Like Red Rock Canyon and some other stops.

But first the Hoover Dam!
Vegas – Pools, shows, fun. We will have most of the day to explore Vegas, and the whole relaxed evening.

Day 13–Las Vegas, NV to Victorville, CA –190 miles

( or we can do Big Bear Lake Option if want, see Ultra Tour below )
We follow the original path of Old Route 66 where we can, and explore the amazing Mojave desert.

Day 14–Victorville to Santa Monica Pier! –100 miles. plus exploring and Malibu Coast Ride!

Over the famous Cajon Pass, then we drop into LA, freeways, civilization. We make it through all the way to the end. The Santa Monica Pier. We can go to Hollywood Blvd today, or we can explore the refreshing California Coast. Malibu, Venice Beach, Santa Monica… let’s keep the Ride Free tradition of ending the tour by putting our feet into the cold Pacific!

We turn the bikes in at the end of the day.

Let’s celebrate tonight!

Day 15–Los Angeles Departure

We say our goodbyes, and plan for our next adventure. There is so much more to see in the USA in the future.

A shuttle will take you to the LAX.