Custom Motorcycle Tours throughout North America!

Toll Free US: 866-225-6688
No Frills 66
A Beautiful 5 Day Slice of Route 66
At 1966 Prices

One of the most well preserved stretches of Route 66 is in Illinois. This no frills tour starting and ending in Chicago will take you the full length of Illinois on Historic Route 66 with stops at many of the treasures that have made 66 so enchanting. We will stay in one of the classic Route 66 hotels that add so much flavor to this tour.


You will walk on the famous Chain of Rocks Bridge, see the majestic Gateway Arch in Saint Louis and so much more!


We will ride along the mighty Mississippi River, stop at Tom Sawyer's boyhood home in Hannibal, Mo. Our adventure brings us through the gorgeous countryside of western Illinois and back to the windy city of Chicago. Your savings on this tour is very substantial, there will be no return charge for your rental motorcycle [not included in tour price] as you will return it to the rental agent in Chicago. We have done everything to make this as affordable as possible.
Included in your tour is a full time professional guide, middle class hotel accommodations, and a nice dinner each night.
Price for Rider and Passenger sharing a room $2500.00
Estimated cost of rental motorcycle Harley Davidson Softail $100.00 per day. Other bikes are available at lower prices.







Route 66

Seldom has any highway been immortalized in song and in literature as much as the fabled highway, Route 66. It symbolizes the pioneering spirit for which Americans have become famous. No longer a U.S. federal highway, or even shown on maps, yet it still exists, albeit under many different highway names.
Don't be fooled by tours that are priced under ours! We have no scheduled tours; this allows you to travel on your schedule, but also increases our costs.
Our tours are never larger than four riders and passengers; your guide always has time for you. Consider that we always include Breakfast, Lunch, And Dinner at good restaurants no fast food unless you request it. Our layover days allow you to sightsee on your own but breakfast and dinner are still included.
Some of it remains intact as it was in its days of glory leading people out of poverty to the Promised Land, the golden State of California.
This motorcycle tour will be available to you, for as few as 5 days, all the way up to 3 weeks for the entire route. We follow the original road wherever it is sensible; some portions have not been maintained for many years. Which ever length you choose this motorcycle adventure is awesome. Around every turn there is beauty and history abounding.
Come along and experience this motorcycle adventure of a lifetime! We will take you on all, or any part of the Mother Road that you please.
Just email RideandFlyTours@Gmail.com or phone Toll Free 866-225-6688 and we will quickly give you a price quote, for a tour customized to your needs.
Ride and Fly Tours specializes in freestyle motorcycle touring giving you the freedom to travel on your schedule and the style, and comfort of your choice.

Route 66 Pricing

Pricing For 14 Days Chicago to LA - Motorcycle Rental Pricing
  • 4 Riders with Private Rooms:
    $4,395 each (cash) | $4,560 (credit card) | Extra layover day $239 each
  • 3 Riders with Private Rooms:
    $4,999 each (cash) | $5,200 (credit card) | Extra layover day $250 each
  • 2 Riders Sharing One Room:
    $5,400 each (cash) | $5,600 (credit card) | Extra layover day $199 each
  • 2 Riders with Private Rooms:
    $6,225 each (cash) | $6,500 (credit card) | Extra layover day $299 each
  • Private Tour (one rider & guide):
    $9,895 (cash) | $10,300 (credit card) | Extra layover day $375
  • Private Tour (rider & passenger):
    $10,675 each (cash) | $11,000 (credit card) | Extra layover day $199
  • Passenger: $775 each | Extra layover day $375 each
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Route 66 Roundrtip

Route 66 Roundtrip
Leave Chicago: 7/18, Arrive LA: 7/31
Leave LA: 8/2, Arrive Chicago: 8/16
Pricing is Route 66 price times two

The ultimate Route 66 tour without a doubt is Roundtrip 66 - starting and ending in Chicago. If you are the kind of guy that wants it all, this is what you have been looking for.
Your trip will begin in Chicago and head through America's heartland past the corn fields that make Illinois the nation’s breadbasket. You’ll stop along the way at many of the Historic Route 66 landmarks that should never be missed.
Through the rolling hills of Missouri we will ride some of the preserved sections of the original Route 66 and travel down into the oil country of Oklahoma, through Indian Reservations and cattle ranches. Then into Texas, the Lone Star State, where the Old West begins and the distant horizon seems unending.
Crossing into New Mexico, you will discover the true beauty of the desert. Then up to Santa Fe, one of the most charming cities of the West. We will take a day off to explore and admire this picturesque town settled by the Spanish in 1607.
Well rested we depart for Arizona, the home of the Grand Canyon, where we will spend a day to see the awesome grandeur of this magical place. Passing through historic Williams, Arizona, our journey takes us across a portion of Death Valley and on into California, the promised land. Here we end the first half of our epic journey of discovery.
Part Two of Roundtrip 66 departs Monday; you are welcome to take either half of this trip or all if you are lucky.
Saying goodbye to LA we will head west for the first time. We’ll go through the mid-lands of California with a look at the western side of Death Valley and into Yosemite National Park. We will spend most of our day exploring the wonders of this place.
Continuing our adventure north past Lake Tahoe, there are numerous pull offs here for pictures you are sure to want. When at Reno, Nevada, Harrah's Auto Museum is a “can't miss” for any car guy.
We now move on across the northern Nevada desert and you will wonder many times how the settlers made it through this inhospitable landscape. Then into Idaho and we’ll see the mountains on the horizon. Next is Grand Teton National Park, one of the most awesome places you will see on this entire trip.
Then we’ll visit Yellowstone National Park. I could ramble on about this wonderful place for the rest of the day and not do it proper justice.
Please take a few minutes to click on the highlighted Yellowstone National Park link and watch some of the videos. We will have a layover day here to relax and explore whatever you wish. After our stay here, we continue to explore the great mountain highways and scenery in Wyoming.
Next to the Black Hills of South Dakota and the iconic Mount Rushmore. We will have another layover day here to explore The Badlands and other Black Hills sights. From here we will cross the Great Plains which is true to its name and a wonderful place for farming.
Then we will take the interstate to our next stop, the rolling hills of southern Minnesota which are a delightful way to arrive at the Mississippi River. Our last day on the road will be a very beautiful one indeed. Winding through the back roads of the Wisconsin dairy land is a truly fitting way to close our trip.
We will cross the State and end at Lake Geneva for our last night together where we will exchange stories of the places we’ve been and sights we’ve seen well into the night. Our friendships from this will last our lifetimes. A short two hour ride in the morning will bring us to the shop to return our motorcycles and then we’ll prepare for the trip home.


Remember you must be a very experienced rider for this tour. Most roads are two lane and some are narrow two lanes. Weather can also come into play such as storms, hail and high winds; these are all things you may encounter. If you are riding your own motorcycle you must have roadside assistance insurance.
We will do our best for anyone who breaks down but in the final result the other members of the tour have a right to continue with their tour. Be assured that you will not be left stranded we will get you to a safe place where you can make arrangements for repairs and are welcome to rejoin the tour at any point.
There will be no refund for partial tours as each member of the tour affects the cost of the other tour participants. There is no chase vehicle you will need to carry your entire luggage on your motorcycle. Ride and Fly Tours assumes no responsibility for loss, damage or theft of your personal effects.
Your decision to tour with Ride and Fly Tours should be made voluntarily, based on your assessment of your abilities, you assume all risks incurred and associated with motorcycling. Ride and Fly Tours does not assume responsibility for your personal health and safety.