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The Great American Diagonal Motorcycle Tour
Chicago ou Los Angeles North America North America 14 days 3620 KM

The Great American Diagonal Motorcycle Tour

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Starting from €2,400 /person
Starting from
€2,400
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Pauline
Roadtrip offered by Pauline
Expert in motorcycle travel in the USA – based in Tours, France
01 86 76 71 00
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This trip is fully custom-made and self-guided, designed to bring your American dream to life along the legendary Route 66, from Chicago to Santa Monica. You keep your freedom on the road while following a carefully crafted itinerary that ensures you don’t miss a thing: Cadillac Ranch, the Grand Canyon, Las Vegas, or the iconic Bagdad Café.

This is not just a road trip, it’s the ultimate American bucket list experience. Over 14 days, you follow the most authentic sections of Route 66, away from major highways, to truly live every myth from the inside. Chicago, Cadillac Ranch, the Grand Canyon, Las Vegas… all the way to the legendary Bagdad Café lost in the desert. Nothing is left to chance: every stop is designed to tick off iconic landmarks and let you fully experience the spirit of the Mother Road.
You will love
    - An original journey from Los Angeles to Chicago
    -Experience Cadillac Ranch, the Grand Canyon and retro diners in a unique order
    -Enjoy the full Route 66 experience at a significantly lower price
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Roadtrip offered by
Pauline
Expert in motorcycle travel in the USA – based in Tours, France
Discover our expert
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Day-by-day itinerary

Day 1

Chicago

The adventure begins with your arrival at Chicago O’Hare International Airport (ORD), one of the major historic hubs of the United States. From the moment you step off the plane, you can already feel the unique energy of this city where Route 66 was born.
After arrival formalities, head to your hotel located in the heart of the Loop, the nerve center of Chicago. This district is no coincidence: it’s where it all begins, where industrial America, modern architecture, and popular culture came together to create a global road myth.
Your first urban immersion begins here. Chicago is an open-air museum:
pioneering skyscrapers, elevated train lines, Art Deco façades, buildings from the Chicago School.
This day is intentionally light. It allows you to land, recover, and start projecting yourself into the journey ahead.
Free evening, where you may enjoy a musical immersion in a legendary jazz club, a direct legacy of the city’s African-American history. Then, taste the famous deep dish pizza, an iconic and almost excessive dish, much like America itself.
Tomorrow, the adventure begins.
Day 2

Chicago - springfield

Departure in the morning from the Loop to reach the dealership and pick up your motorcycle (or SUV). This moment marks a real transition: the dense city gives way to a more horizontal, more readable America.
First stop in Wilmington, in front of the Gemini Giant. This fiberglass colossus is one of those roadside figures created in the 1950s to attract motorists. It perfectly embodies the commercial and carefree spirit of Route 66.
In Joliet, stop by the former prison made famous by The Blues Brothers, then pass by the Rialto Square Theatre, opened in 1926, a witness to the golden age of popular entertainment.
The road then leads to Pontiac, where car enthusiasts and road culture lovers will find plenty to enjoy: Route 66 Hall of Fame, monumental murals, Pontiac Museum. America tells its own myth in the open air.
At the end of the day, pass through Litchfield and its Skyview Drive-In, an open-air cinema operating since 1950. Even without a screening, the place tells the story of a time when the car was at the center of everything.
Arrival in Springfield, overnight stay. Dinner possible at Obed & Isaac or at Cozy Dog Drive-In, famous for popularizing the corn dog.
350
Day 3

Springfield - St-Louis

Before leaving Springfield, a subtle but important reminder: Abraham Lincoln lived here. Route 66 is never far from great History.
Leaving the city, ride along the Illinois Brick Road, one of the last original paved sections still visible. The road is felt physically, irregular, deeply rooted.
We recommend a stop in Cuba, nicknamed the Route 66 Mural City. This small Missouri town features 14 outdoor murals depicting scenes from local and national history.
Take a break in Carlinville, then gradually enter the St. Louis metropolitan area. The landscape becomes more urban, industrial, marked by the Mississippi River.
Upon arrival, explore downtown on foot. The Gateway Arch dominates the skyline: it symbolizes westward expansion more than Route 66 itself. The massive underground stadium is also worth a look.
In the evening, a must-stop at Ted Drewes Frozen Custard, a local institution since 1929, famous for its ice creams.
180
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Day 4

St-Louis - Joplin

Leaving St. Louis, Route 66 gradually moves away from major infrastructure to return to a more human scale. Miles pass through a succession of small towns and typical Midwest agricultural landscapes.
This is where you understand that Route 66 is not just a mythical road, but also a daily life axis, used for decades by families, workers, and anonymous travelers.
Arrival in Joplin marks an interesting transition. The city has preserved and highlighted several elements of its Route 66 heritage, particularly through its murals and restored signage.
A free walk allows you to follow the Route 66 Mural & Neon Photo Tour, a true open-air journey telling the local story, the golden age of the road, and its recent revival.
Recommended break at Joplin Avenue Coffee, an independent café with a contemporary aesthetic, appreciated by locals and travelers alike.
Free evening to explore the streets or simply enjoy the calm after a day on the road.
450 km
Day 5

Joplin - Oklahoma City

Entering Oklahoma happens smoothly. The landscapes open up, the straight lines stretch out, announcing the vast spaces of the country’s center. Tulsa appears as a key stop to understand the cultural impact of Route 66.
Visiting the Woody Guthrie Center is a highlight of the day. Woody Guthrie, a major figure of American folk music, accompanied Dust Bowl migrants through his songs, many of whom traveled Route 66 to escape hardship.
The museum connects music, social history, and the road, giving deeper meaning to the miles traveled.
Then head to 11th Street, the former Route 66 alignment in Tulsa. Neon signs, old motels, and diners tell the story of a time when the road was a constant meeting place.
We recommend eating at Mother Road Market, a modern food hall reinterpreting the spirit of Route 66 through a diverse culinary offering.
Depending on your mood, the evening can continue in a bar with live music, in a country or rockabilly atmosphere.
200 km
Day 6

Day 7

Day 8

Day 9

Day 10

Day 11

Day 12

Day 13

Day 14

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Experience feedback

Starting from €2,400 /person
Pauline
Roadtrip offered by Pauline
Expert in motorcycle travel in the USA – based in Tours, France

Passionate about the vast American landscapes, Pauline designs unique motorcycle journeys across the United States. With thousands of miles of riding experience, she creates itineraries combining iconic roads and spectacular scenery.

Discover our expert
Request a free quote
Day 1
Chicago
The adventure begins with your arrival at Chicago O’Hare International Airport (ORD), one of the major historic hubs of the United States. From the moment you step off the plane, you can already feel the unique energy of this city where Route 66 was born.
After arrival formalities, head to your hotel located in the heart of the Loop, the nerve center of Chicago. This district is no coincidence: it’s where it all begins, where industrial America, modern architecture, and popular culture came together to create a global road myth.
Your first urban immersion begins here. Chicago is an open-air museum:
pioneering skyscrapers, elevated train lines, Art Deco façades, buildings from the Chicago School.
This day is intentionally light. It allows you to land, recover, and start projecting yourself into the journey ahead.
Free evening, where you may enjoy a musical immersion in a legendary jazz club, a direct legacy of the city’s African-American history. Then, taste the famous deep dish pizza, an iconic and almost excessive dish, much like America itself.
Tomorrow, the adventure begins.
Request a free quote
Day 2
Chicago - springfield
Departure in the morning from the Loop to reach the dealership and pick up your motorcycle (or SUV). This moment marks a real transition: the dense city gives way to a more horizontal, more readable America.
First stop in Wilmington, in front of the Gemini Giant. This fiberglass colossus is one of those roadside figures created in the 1950s to attract motorists. It perfectly embodies the commercial and carefree spirit of Route 66.
In Joliet, stop by the former prison made famous by The Blues Brothers, then pass by the Rialto Square Theatre, opened in 1926, a witness to the golden age of popular entertainment.
The road then leads to Pontiac, where car enthusiasts and road culture lovers will find plenty to enjoy: Route 66 Hall of Fame, monumental murals, Pontiac Museum. America tells its own myth in the open air.
At the end of the day, pass through Litchfield and its Skyview Drive-In, an open-air cinema operating since 1950. Even without a screening, the place tells the story of a time when the car was at the center of everything.
Arrival in Springfield, overnight stay. Dinner possible at Obed & Isaac or at Cozy Dog Drive-In, famous for popularizing the corn dog.
350
Request a free quote
Day 3
Springfield - St-Louis
Before leaving Springfield, a subtle but important reminder: Abraham Lincoln lived here. Route 66 is never far from great History.
Leaving the city, ride along the Illinois Brick Road, one of the last original paved sections still visible. The road is felt physically, irregular, deeply rooted.
We recommend a stop in Cuba, nicknamed the Route 66 Mural City. This small Missouri town features 14 outdoor murals depicting scenes from local and national history.
Take a break in Carlinville, then gradually enter the St. Louis metropolitan area. The landscape becomes more urban, industrial, marked by the Mississippi River.
Upon arrival, explore downtown on foot. The Gateway Arch dominates the skyline: it symbolizes westward expansion more than Route 66 itself. The massive underground stadium is also worth a look.
In the evening, a must-stop at Ted Drewes Frozen Custard, a local institution since 1929, famous for its ice creams.
180
Request a free quote
Day 4
St-Louis - Joplin
Leaving St. Louis, Route 66 gradually moves away from major infrastructure to return to a more human scale. Miles pass through a succession of small towns and typical Midwest agricultural landscapes.
This is where you understand that Route 66 is not just a mythical road, but also a daily life axis, used for decades by families, workers, and anonymous travelers.
Arrival in Joplin marks an interesting transition. The city has preserved and highlighted several elements of its Route 66 heritage, particularly through its murals and restored signage.
A free walk allows you to follow the Route 66 Mural & Neon Photo Tour, a true open-air journey telling the local story, the golden age of the road, and its recent revival.
Recommended break at Joplin Avenue Coffee, an independent café with a contemporary aesthetic, appreciated by locals and travelers alike.
Free evening to explore the streets or simply enjoy the calm after a day on the road.
450 km
Request a free quote
Day 5
Joplin - Oklahoma City
Entering Oklahoma happens smoothly. The landscapes open up, the straight lines stretch out, announcing the vast spaces of the country’s center. Tulsa appears as a key stop to understand the cultural impact of Route 66.
Visiting the Woody Guthrie Center is a highlight of the day. Woody Guthrie, a major figure of American folk music, accompanied Dust Bowl migrants through his songs, many of whom traveled Route 66 to escape hardship.
The museum connects music, social history, and the road, giving deeper meaning to the miles traveled.
Then head to 11th Street, the former Route 66 alignment in Tulsa. Neon signs, old motels, and diners tell the story of a time when the road was a constant meeting place.
We recommend eating at Mother Road Market, a modern food hall reinterpreting the spirit of Route 66 through a diverse culinary offering.
Depending on your mood, the evening can continue in a bar with live music, in a country or rockabilly atmosphere.
200 km
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Day 6
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Day 7
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Day 8
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Day 9
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Day 10
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Day 11
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Day 12
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Day 13
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Day 14

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Starting from €2,400 /person
On the dates of your choice
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Price details

The price includes
-13 nights in a double room in 4-star accommodations -Motorcycle rental with model choice (or SUV on request) -Helmet and side saddlebags provided -Unlimited mileage -A SIM card with 10GB of data
The price does not include
-International flights -Meals and drinks during the trip -Mandatory motorcycle insurance to be taken out locally -Optional Planet Ride travel insurance -Optional activities mentioned in the itinerary (helicopter flight, limousine tour in Las Vegas…) -Anything not specified in “price includes”
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