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18 Days Historic Route 66 Motorcycle Tours USA

Chicago, Cook County, Illinois, USA

Stunning Route 66 Motorcycle Trip

This listing has the most popular offer available in The Americas & Caribbean

When you tell someone that you are going on a motorbike tour in America, they will immediately ask whether you are taking Route 66. This ‘mother road’ or ‘main street of America’ was constructed in 1926 to make the Wild West accessible. It will take you straight through eight different states. Along the way, you will see the Grand Canyon and Las Vegas, and after 2,400 miles, you will end this motorbike tour in Santa Monica at the breakers of the Pacific.

Key information

  • Terrain: asphalt
  • Bike: rental bike (BMW, Harley, Yamaha, Honda, Suzuki models)
  • Mileage: 2,500 miles / 4,024 kilometers
  • Daily rides: 140 - 260 miles / 226 - 419 kilometers
  • Meals: some breakfasts


  • Spend a night in Las Vegas
  • Riding along the historic Route 66
  • Professional tour guide accompaniment
  • Starts in Chicago and ends in Los Angeles
  • Ride along country lanes, passing plenty of farms and typical country houses
  • Motorcycle rental of your choice during the tour
  • 17 nights’ accommodation
  • Airport transfers

Skill level

  • Beginner
  • Intermediate


13 riding days in English
The organizer also speaks: Dutch, German
Airport transfer included: O'Hare International Airport
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During your journey, you will stay in good quality hotels, which will be reserved before departure. The room will be in a standard twin / double room accommodation. You can opt for a private room for an additional single supplement. All rooms will include en-suite bathroom with shower or bath facilities, television, and air conditioning. Most hotels will also have a pool.


Day 1: Arrival in Chicago

Today is your arrival in Chicago. You will be taken to your comfortable hotel.

Day 2: Chicago (free day)

To start off, you will spend a day in Chicago, home to Al Capone (in his day) and Oprah Winfrey (currently). You can shop till you drop down the famous shopping street ‘Magnificent Mile,’ go up onto the sky deck at the top of the famous Sears Tower, relax on a bench in Lincoln Park, or take a stroll down Navy Pier. There are too many fun options to mention.

Day 3: Chicago - Lincoln, 190 miles / 306 kilometers

Today, you will leave the city behind the team on your two-wheelers and carry on along country lanes, passing plenty of farms, and typical country houses. The first few old-school petrol stations of Route 66 will start to pop up, and in McLean, you will see the first few big grain silos.

Day 4: Lincoln - St. Louis, 140 miles / 226 kilometers

In the state of Alabama, you will pass through Mount Olive, which houses many old mines, and you will stop to visit a typical roadhouse and hamburgers galore! Then on to the Mississippi River and St. Louis, where you will take your time to have a nosey around.

Day 5: St. Louis - Lebanon, 200 miles / 322 kilometers

Today you will ride on Interstate 44, passing numerous typical American in-the-middle-of-nowhere towns. Now and then, you will ride down bits of the highway, yeehaw! You will stay the night in Lebanon in the state of Missouri.

Day 6: Lebanon - Miami, 165 miles / 266 kilometers

Via Springfield and Joplin, you will reach Miami (Oklahoma). It is a small town in Oklahoma named after the Indian Myaamia tribe. Taking in parts of Kansas too, you will pass plenty of typical Route 66 souvenir shops along the way, where you will have ample opportunity to haggle.

Day 7: Miami - Oklahoma City, 220 miles / 355 kilometers

Heading through the middle of the state, you will visit Tulsa, the former Indian territory, which before it was taken by the Texans, was well-known for its wealth in oil wells. The most famous resident of Tulsa is the musician JJ Cale, known for his contributions to the Eric Clapton songs After Midnight and Cocaine. Crossing many old arch bridges you will rumble on to the state capital.

Day 8: Oklahoma City - Amarillo, 260 miles / 419 kilometers

There will be no need to ask for directions, your team leader will show you the way to Amarillo. Riding down Highway 40, you will enter Texas via Elk City. There is a lot to see and do in this typical Texan city.

Day 9: Amarillo - Santa Fe, 260 miles / 419 kilometers

Visiting the Cadillac Ranch, you will find out how Cadillac cars got an overwhelmingly more artistic and colorful treatment than other cars. Afterward, you will enter New Mexico and reach your destination at Santa Fe with its adobe-style houses.

Day 10: Santa Fe - Gallup, 220 miles / 355 kilometers

Be sure to take plenty of water with you today as, via Albuquerque, you will enter the New Mexico desert. Your lodging for the night will be in Gallup, also known as ‘the Indian capital of the world’ because of its wide range of tribal descendants, such as the Hopi, Zuni, and Navajo Indian tribes.

Day 11: Gallup - Flagstaff, 210 miles / 338 kilometers

Today, reaching the area belonging to Navajo Indians, you will visit the petrified forest in the state of Arizona. The ‘forest’ takes its name from the many petrified trees and fossils, but nowadays it is mainly desert. You will stay the night at the accommodation alongside the old Route 66.

Day 12: Flagstaff (free day)

After a nice little sleep in, you will have the opportunity to explore the Grand Canyon. Along the South Rim, you will take lasting memories of each other with a backdrop of the 277-mile long crevice, which is even visible from the moon. The recommendations are a thrilling helicopter ride over the Canyon and a visit to the Imax Theater after which you will know everything about the Grand Canyon.

Day 13: Flagstaff - Kingman, 160 miles / 258 kilometers

After breakfast, you will cruise on towards Seligman via Williams. The takers can get a shave at the well-known Angels barbershop.

Day 14: Kingman - Las Vegas, 150 miles / 242 kilometers

Via Ed’s Camp and Oatman, you will enter the state of Nevada, where you will temporarily leave Route 66 to spend the evening and night in the entertainment city of Las Vegas. Have great fun amidst the immense variety in music, casinos that big enough to fit entire villages, and the diversity of people who come from all over the world to experience Las Vegas. Boredom is not an option in the city that never sleeps!

Day 15: Las Vegas - Barstow, 160 miles / 258 kilometers

After a stop in Jerome to visit the open-air museum ‘Ghost Town’, you will arrive in sunny California and stay the night at the miners' town of Barstow, where you will once more pick up the mother road thread.

Day 16: Barstow - Los Angeles, 165 miles / 266 kilometers

You will bring the 'get-your-kicks-on-route-66 feeling' to a close with a magnificent ride through the hills of California, ending up at the Pacific Ocean in Santa Monica. Do not be afraid to shed a tear when you say farewell to your trusted two-wheelers.

Day 17: Los Angeles

You are free to do as you please on your last day here. There is a huge variety of tourist attractions to choose from. USA on Wheels recommends a day trip to Universal Studios, a limousine ride through Hollywood, or enjoying a lazy day at Venice Beach.

Day 18: Departure day

In the early morning, the team will take you to the airport to embark on your journey home or, if you wish to extend your stay, USA on Wheels are happy to take you through your possibilities and organize any additional wishes.

Bike options

Category 1

  • Suzuki Intruder 800 (V-twin engine, 815cc, 5 gears, 70 centimeters seat height, 246 kilograms, 15,5 liters fuel tank capacity, and windshield)
  • Honda Shadow 750 (V-twin engine, 745cc, 5 gears, 66 centimeters seat height, 251 kilograms, 14 liters fuel tank capacity, and windshield)

Category 2

  • Harley-Davidson Sportster 883 (V-twin engine, 883cc, 5 gears, 68 centimeters seat height, 255 kilograms, 17 liters fuel tank capacity, and windshield)
  • Yamaha 950 Tourer (V-twin engine, 950cc, 5 gears, 67 centimeters seat height, 298 kilograms, 17 liters fuel tank capacity, windshield, and suitcase)
  • Harley-Davidson Sportster 1200 (V-twin, 1200cc, 5 gears, 68 centimeters seat height, 255 kilograms, 17 liters fuel tank capacity, and windshield)
  • Yamaha XVS 1300 (V-twin engine, 1300cc, 5 gears, 72 centimeters seat height, 283 kilograms, 19 liters fuel tank capacity, windshield, bags, and sissy bar)

Category 3

  • Honda VTX1300 (V-twin engine, 1304cc, 5 gears, 72 centimeters seat height, 283 kilograms, 19 liters fuel tank capacity, windshield, luggage, bags, and sissy bar)
  • Harley-Davidson Road King (V-twin engine, 1670cc, 6 gears, 72 centimeters seat height, 355 kilograms, 23 liters fuel tank capacity, windshield, and luggage)
  • Harley-Davidson Heritage (V-twin engine, 1670cc, 6 gears, 65 centimeters seat height, 326 kilograms, 19 liters fuel tank capacity, windshield, luggage, bags, and sissy bar)

Category 4

  • Honda ST1300 (V-twin, 4 cyl engine, 1261cc, 5 gears, 79 centimeters seat height, 300 kilograms, 29 liters fuel tank capacity, windshield, and luggage)
  • Honda GL1800 Goldwing (boxer 6 cyl engine, 1832cc, 5 gears, 74 centimeters seat height, 405 kilograms, 25 liters fuel tank capacity, windshield, and koffe)
  • BMW R1200GS (boxer 2 cyl engine, 1170cc, 6 gears, 85 centimeters seat height, 220 kilograms, 20 liters fuel tank capacity, and windshield)
  • BMW R1200RT (V-twin engine, 1170cc, 6 gears, 82 centimeters seat height, 263 kilograms, 25 liters fuel tank capacity, windshield, and luggage)
  • Harley-Davidson Street Glide (V-twin engine, 1670cc, 6 gears, 73 centimeters seat height, 370 kilograms, 23 liters fuel tank capacity, windshield, and luggage)
  • Harley-Davidson Ultra Glide (V-twin engine, 1670cc, 6 gears, 73 centimeters seat height, 370 kilograms, 23 liters fuel tank capacity, windshield, and luggage)

Skill levels required for this tour: beginner and intermediate

Please note that the pace of the tour can be at a beginner's level as well as at an intermediate's level. It all depends on the group's experience and own pace. Please send an inquiry for more details.


  • can ride for 2-3 hours
  • minimal riding experience
  • assistance required
  • comfortable with curves and leans
  • basic experience with unsurfaced roads
  • short distance ascents and descents


  • can ride for 3-4 hours
  • average riding experience
  • little assistance required
  • comfortable with extreme curves and leans
  • average experience with unsurfaced roads
  • steep ascents and descents

Tour information

  • Roads in the USA are in good condition. Congestion is minimal, apart from in big cities, and the roads are very well signposted. There are a number of traffic regulations that differ from those in the UK. Your team leader will discuss the most important ones with you.
  • In principal, you will ride in convoy. However, if you wish to ride part of the journey on your own, you can discuss this with your team leader.
  • You will be riding at a reasonable pace, as the aim, of course, is to see as much as possible. However, you will frequently be riding down bendy roads, which will require some confidence.
  • You are required to have a valid (motorbike) driving license. However, you will not need an international driving license.

Included excursions

  • Shopping at Magnificent Mile
  • Visit the sky deck at the top of the famous Sears Tower
  • Take a stroll down Navy Pier
  • Explore the Grand Canyon
  • Visit the open-air museum ‘Ghost Town’


This journey starts in Chicago and ends in Los Angeles, USA. The journey will go through the Route 66 and cover several places such as:

  • Lincoln
  • St. Louis
  • Lebanon
  • Miami
  • Oklahoma City
  • Amarillo
  • Santa Fe
  • Gallup
  • Flagstaff
  • Kingman
  • Las Vegas
  • Barstow
  • Los Angeles


Some continental breakfasts are included in this tour.

The following meals are included:

  • Breakfast

The following dietary requirement(s) are served and/or catered for:

  • Regular (typically includes meat and fish)
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

Things to do (optional)

  • Enjoy a limousine ride through Hollywood
  • Have a day trip to Universal Studios
  • Stroll around and explore the entertainment at Las Vegas
  • Try a helicopter riding
  • Visit the Imax Theater
  • Visit the well-known Angels barbershop

What's included

  • 17 nights’ accommodation
  • A trailer with a spare engine where there is also room for luggage
  • Motorbike rental with liability insurance
  • Some continental breakfasts
  • Tax
  • Tour guide
  • Transfers

What's not included

  • Airfare
  • Cancellation insurance (5.50% of the fare)
  • Entrance fees
  • High season surcharge (on departures from 15 May to 16 August at 220 EUR)
  • Other meals than mentioned
  • Personal expenses
  • Petrol
  • Travel insurance
  • ZERO-Risk insurance (without deductible, high liability): 29 EUR per day

How to get there

Recommended Airports

Arrival by airplane

Please book your flight to arrive at Chicago - O'Hare International Airport (ORD). Transfer from and to the airport is included. USA on Wheels will pick you up from the airport.

Airport: O'Hare International Airport Airport transfer included: O'Hare International Airport No additional charges. You can request this in the next step.

Cancellation Policy

  • A reservation requires a deposit of 20% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid 70 days before arrival.

Value for money
Accommodation & facilities
Quality of activity
18 days / 17 nights
from --
Pricing information

If you are interested in a package that cannot be chosen from the list below, kindly advise USA on Wheels in your message and the package price will be updated accordingly.

  • Single supplement: 1,090 EUR
  • Pillion: 1,990 EUR
  • Zero-risk insurance: 29 EUR per day

Tour information

This tour requires a minimum of eight riders.

Tuesday June 2, 2020
(18 days / 17 nights)

Select your package:

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