Route 66 - Eastern Part: Chicago IL to Albuquerque NM in 8 days!

Included: free day-trip to Milwaukee
to visit the Harley-Davidson Museum!

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The Eastern Section of Route 66

Tour dates (English)

tour dates route66 May 23, 2024 - May 30, 2024
tour dates route66 May 29, 2024 - Jun 05, 2024 - Sold out
tour dates route66 May 30, 2024 - Jun 06, 2024
tour dates route66 Jun 20, 2024 - Jun 27, 2024 - Few spots remaining
tour dates route66 Jun 27, 2024 - Jul 04, 2024 - Sold out
tour dates route66 Jul 11, 2024 - Jul 18, 2024
tour dates route66 Jul 25, 2024 - Aug 01, 2024
tour dates route66 Aug 08, 2024 - Aug 15, 2024
tour dates route66 Aug 22, 2024 - Aug 29, 2024 - Few spots remaining
tour dates route66 Aug 29, 2024 - Sep 05, 2024
tour dates route66 Sep 04, 2024 - Sep 11, 2024
tour dates route66 Sep 05, 2024 - Sep 12, 2024 - Sold out
tour dates route66 Sep 12, 2024 - Sep 19, 2024 - Sold out
tour dates route66 Sep 19, 2024 - Sep 26, 2024
tour dates route66 Oct 05, 2024 - Oct 12, 2024
tour dates route66 Apr 03, 2025 - Apr 10, 2025
tour dates route66 Apr 24, 2025 - May 01, 2025
tour dates route66 May 07, 2025 - May 14, 2025
tour dates route66 May 08, 2025 - May 15, 2025
tour dates route66 May 22, 2025 - May 29, 2025
tour dates route66 May 28, 2025 - Jun 04, 2025
tour dates route66 May 29, 2025 - Jun 05, 2025
tour dates route66 Jun 19, 2025 - Jun 26, 2025
tour dates route66 Jun 26, 2025 - Jul 03, 2025
tour dates route66 Jul 10, 2025 - Jul 17, 2025
tour dates route66 Jul 24, 2025 - Jul 31, 2025
tour dates route66 Aug 07, 2025 - Aug 14, 2025
tour dates route66 Aug 21, 2025 - Aug 28, 2025
tour dates route66 Aug 28, 2025 - Sep 04, 2025
tour dates route66 Sep 03, 2025 - Sep 10, 2025
tour dates route66 Sep 04, 2025 - Sep 11, 2025
tour dates route66 Sep 11, 2025 - Sep 18, 2025
tour dates route66 Sep 18, 2025 - Sep 25, 2025
tour dates route66 Oct 02, 2025 - Oct 09, 2025
tour dates route66 Oct 16, 2025 - Oct 23, 2025

Tour dates (German Exclusive Language)

tour dates route66 May 30, 2024 - Jun 06, 2024
tour dates route66 Aug 08, 2024 - Aug 15, 2024
tour dates route66 Aug 29, 2024 - Sep 05, 2024
tour dates route66 Sep 19, 2024 - Sep 26, 2024
tour dates route66 May 08, 2025 - May 15, 2025
tour dates route66 May 29, 2025 - Jun 05, 2025
tour dates route66 Aug 07, 2025 - Aug 14, 2025
tour dates route66 Aug 28, 2025 - Sep 04, 2025
tour dates route66 Sep 18, 2025 - Sep 25, 2025

Tour dates (Italian Exclusive Language)

tour dates route66 May 23, 2024 - May 30, 2024
tour dates route66 Jun 27, 2024 - Jul 04, 2024 - Sold out
tour dates route66 Jul 25, 2024 - Aug 01, 2024
tour dates route66 Sep 05, 2024 - Sep 12, 2024 - Sold out
tour dates route66 May 22, 2025 - May 29, 2025
tour dates route66 Jun 26, 2025 - Jul 03, 2025
tour dates route66 Jul 24, 2025 - Jul 31, 2025
tour dates route66 Sep 04, 2025 - Sep 11, 2025

Tour dates (Spanish Exclusive Language)

tour dates route66 May 23, 2024 - May 30, 2024
tour dates route66 Jun 27, 2024 - Jul 04, 2024 - Sold out
tour dates route66 Jul 25, 2024 - Aug 01, 2024
tour dates route66 Sep 05, 2024 - Sep 12, 2024 - Sold out
tour dates route66 May 22, 2025 - May 29, 2025
tour dates route66 Jun 26, 2025 - Jul 03, 2025
tour dates route66 Jul 24, 2025 - Jul 31, 2025
tour dates route66 Sep 04, 2025 - Sep 11, 2025

Tour dates (French Exclusive Language)

tour dates route66 May 29, 2024 - Jun 05, 2024 - Sold out
tour dates route66 Jun 20, 2024 - Jun 27, 2024 - Few spots remaining
tour dates route66 Aug 22, 2024 - Aug 29, 2024 - Few spots remaining
tour dates route66 Sep 04, 2024 - Sep 11, 2024 - Sold out
tour dates route66 Sep 12, 2024 - Sep 19, 2024 - Sold out
tour dates route66 Apr 24, 2025 - May 01, 2025
tour dates route66 May 07, 2025 - May 14, 2025
tour dates route66 May 28, 2025 - Jun 04, 2025 - Few spots remaining
tour dates route66 Jun 19, 2025 - Jun 26, 2025
tour dates route66 Jul 10, 2025 - Jul 17, 2025
tour dates route66 Aug 21, 2025 - Aug 28, 2025
tour dates route66 Sep 03, 2025 - Sep 10, 2025
tour dates route66 Sep 11, 2025 - Sep 18, 2025
tour dates route66 Oct 02, 2025 - Oct 09, 2025

Tour rates (per person)

Various discounts may apply (season, group booking, early-bird, last-minute etc - please always contact us for your special rate)

Guided Tours:

1 rider 1 motorcycle 1 room, from: US$4,750.00 (£3,752.00, AU$7,172.00, NZ$7,885.00, 4.370,00 €)

2 people 1 motorcycle 1 room, per person from: US$2,375.00 (£1,876.00, AU$3,586.00, NZ$3,942.00, 2.185,00 €)

2 people 2 motorcycles 1 room, per person from: US$3,159.00 (£2,496.00, AU$4,770.00, NZ$5,244.00, 2.906,00 €)

Using your own motorcycle on this tour: not allowed.

It is possible to join a guided tour with a rental car (convertible or other categories) - please ask for details.

Self-Guided Tours:

1 rider 1 motorcycle 1 room, from: US$3,200.00 (£2,528.00, AU$4,832.00, NZ$5,312.00, 2.944,00 €)

2 people 1 motorcycle 1 room, per person, from: US$1,683.00 (£1,330.00, AU$2,541.00, NZ$2,794.00, 1.548,00 €)

2 people 2 motorcycles 1 room, per person, from: US$2,406.00 (£1,901.00, AU$3,633.00, NZ$3,994.00, 2.214,00 €)

Day 1: Chicago, IL - arrival day

After touching down at Chicago International Airport we ask you to transfer to your hotel. Chicago, it almost goes out with saying, is one hell of a town; the largest, most vibrant of the Great Lake cities. The city skyline has few peers and down on the streets you’ll find a fantastic selection of world class museums, restaurants and cafes. There is also the city’s famed bar and nightclub scene that is still anchored in an incredible jazz and blues tradition. The fun begins with a Welcome Dinner and drinks with your fellow riders, and ends in one of Chicago's finest hotels, The Drake. In the morning the long dreamt of journey across Route 66 begins.

standard route 66 tour bike motorcycle
A little piece of brick road from 1931. Auburn, IL

Day 2: Chicago, IL - Springfield, IL (Miles: 187, Kilometers: 301)

First order of business is to pick up your Harley-Davidson before you can start on the ultimate American road trip. Parallel to I-55, (the Interstate 55) the legendary Route 66 began its run right here. It cut through the state before it ran the whole way to the Pacific Coast. Along the way you’ll see old-time diners and service stations which are a real slice of Americana. Riding South from Chicago, we will pass the old archetypal truck stop town of McLean, but we don’t linger, instead we barrel through the coal-mining area of Illinois and continue along the Pontiac Trail, as this road used to be known. Finally we pull into Springfield, the Illinois state capital. You can choose between staying at either the Hilton Downtown Springfield or the historic Abraham Lincoln Hotel. Both hotels are just a stone’s throw from the site of Abraham Lincoln's Illinois home.

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Chain of Rocks Bridge over Mississippi River, St. Louis, MO

Day 3: Springfield, IL - St. Louis, MO (Miles: 116, Kilometers: 187)

Making our way south, we head towards the state of Missouri on our way to St. Louis, a town rich in history. Along the way, we will pass through a number of Highway towns, which are great places for a stop en route. One thing’s for sure, you should see the famous Dixie truck stop, "Our Lady of the Highway Statue", Litchfield and the "Ariston Café". We will also set aside some time to visit Meramec Caverns as you head for the Mississippi River – a complex of mineral formations which are as rare as they are exquisite. And of course we couldn’t miss the famous "Chain of Rocks Bridge". Now we are properly in Missouri, the state where the Mississippi River meets the Missouri River, and where you can find both forests meet the grassland prairies. It’s a short ride from the state border into the "Gateway to the West," St. Louis, a dynamic and cultured city nestled along the shores of the almighty Mississippi River. You will find not only some of the best live music, but also BBQ ribs in the entire United States in St. Louis. You can also study the magnificent St. Louis Arch from the window of tonight’s accommodations, the centrally located Hampton Inn.

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Beautiful country roads in Missouri

Day 4: St. Louis, MO - Joplin, MO (Miles: 335, Kilometers: 539)

It’s a nice idea to get up a little early before we hit the road. Take a short walk across the street and marvel at an early morning view of the St. Louis Arch and Mississippi River. Soon after we will have St. Louis in our rear view mirrors as we leave the city for the rolling Missouri hills. You will soon see why this is such a popular stretch for riders, especially after working up an appetite for a lunch stop at a place in the middle of nowhere that serves about the best darn BBQ you will ever eat! Tonight we stay in Joplin, a city still recovering from a massive tornado in 2011. We'll meet some of the locals in the downtown neighborhood and hear some hair-raising stories about how it felt to be in the eye of a deadly tornado!

standard route 66 tour bike motorcycle
The "Pony" Bridge near Bridgeport, OK

Day 5: Joplin, MO - Oklahoma City, OK (Miles: 255, Kilometers: 411)

Making tracks from Joplin we ride west through Oklahoma, following the contour of a landscape that feels as if it’s always been there. We cover 100 miles between Tulsa and Oklahoma City through what was known in the Old West as Indian country. In the 1830s this land, which was considered basically worthless, was set aside as Indian Territory. It became an expedient dumping ground for the so-called Five Civilized Tribes who had previously acted as a check on white settlement in the southern states. The Seminole of Florida, the Choctaw and the Chickasaw of Mississippi, and the Creek of Alabama were each assigned a share, and the rest was assigned to the Cherokee from Georgia, Carolina and Tennessee. The state still has a large Native American Indian population to this day. As you may or may not already know, "Oklahoma" is actually the Choctaw word for "red man". As we head west we travel through El Reno and then ride over the mile-long bridge, near Bridgeport and straight into Oklahoma City. Be sure and enjoy your stay tonight in the heart and soul of Route 66 country! Your hotel is handily located in the Bricktown Neighborhood, which is packed with shops, restaurants and nightlife.

standard route 66 tour bike motorcycle
72oz (2kg) steak. Free if you can eat it! Amarillo, TX

Day 6: Oklahoma City, OK - Amarillo, TX (Miles: 266, Kilometers: 428)

We get up nice and early for our trip into the Panhandle, the southernmost portion of the Great Plains. Frequently referred to as "the real Texas", the Panhandle really lives up to the popular stereotype of how Texas is supposed to look. Where the buffalo once roamed and the indigenous peoples once lived was considered perilous and uninhabitable frontier country. However its value went up sharply during the 1870s as a source of natural resources - specifically Helium, especially in Amarillo, and oil. Together with agriculture, this brought enormous wealth to the region. Although Amarillo can seem cut off, even from the rest of Texas, it sits on one of the great American cross-country routes – the I-40 (once a part of legendary Route 66), roughly 300 miles from Albuquerque and 250 miles west of Oklahoma City. Home to a few of the world’s largest cattle ranches, Amarillo takes its name from Spanish and means "yellow", the color so distinctive to this territory. The illustrious Ambassador Hotel in Downtown Amarillo will be our hosts this evening. Not only that but our good buddies from "The Big Texan Steakhouse" will pick everybody up at the hotel in a fleet of old Cadillacs with giant bull horns across the hood. On tonight’s menu are the finest steaks in the whole of Texas!

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Cadillac Ranch, near Amarillo, TX

Day 7: Amarillo, TX - Santa Fe, NM (Miles: 303, Kilometers: 488)

It’s time to bid a fond farewell to the Lone Star State. We’re on our way to "The Land of Enchantment", that is New Mexico. After passing through the eccentric and colorful art installation known as Cadillac Ranch, we come to the highly atmospheric ghost town of Glen Rio, where you can stand with one foot in Texas and the other in New Mexico. At this stage of the trip, we have 5 states behind us and 3 still ahead. The ride continues through the land of Comanche Indians and into Tucumcari, the largest town between Albuquerque and Amarillo. Then we head up into the High Plains and the slightly dizzying altitudes of Santa Fe in central New Mexico. Santa Fe is one of the oldest and most picturesque cities in the United States. It will be our base for the following two nights, in a hotel just steps from the historic town square and mission, in the heart of Santa Fe’s Old Town.

standard route 66 tour bike motorcycle
Horseback riding, Santa Fe, NM

Day 8: Santa Fe, NM - Albuquerque, NM(Miles: 65, Kilometers: 104)

Only a short ride left today to return our motorcycles. Please let us know if you need a day or two to enjoy the sights and many galleries Santa Fe offers!

Harley-Davidson Museum In Milwaukee
Harley-Davidson Museum In Milwaukee

Harley-Davidson Headquarters and Museum Experience: add this free daytrip to your Route 66 tour!

We arrange your complimentary return train tickets from/to Chicago and the HD Museum tickets as well. You leave Chicago at 8:30AM and will be back by 3PM.

You not only visit this world-class Harley-Davidson museum but will have the opportunity to shop in the H-D Corporate Store, an experience that is typically reserved for employees and partners. This is the only place in the world where you can purchase a Harley-Davidson t-shirt with "Juneau, Wisconsin," the street the HQ sits on, as the location. It’s a pretty safe bet you will be the only person in your riding club, or even in your home city, that has the coveted "Juneau" t-shirt.

Cancellation terms

Because of the chance of illness, accident, airline inefficiency, company insolvency or other unforeseen situations that may cause a customer (you) to miss a tour, we suggests to purchase travel/medical/health/trip cancellation insurance. It is a little expense that gives you piece of mind, highly recommended!

Insurance

Various motorcycle insurances are available that you can book with your rental, for more information please have a look at our Insurance webpage.

What's included in guided tours?

What's not included in guided tours?

What's included in self-guided tours?

What's NOT included in self-guided tours?

To book this tour we need following information from you:

Please note: please do not purchase domestic/international airline tickets until tour is confirmed by us!

Book your own programs:

3104 E Camelback Rd., PMB #2100, Phoenix, AZ 85016. Phone: 1 (602) 354-9292
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