North America
Route 66 — Chicago to Santa Monica
Days
16
Riding days
12
Miles
2210
Longest day
310 mi
Difficulty
Moderate
Best season
April to October is the ideal window. Avoid July and August in the desert states (AZ, NM, TX) where temperatures regularly exceed 40°C. May, June and September offer the best balance of comfortable riding temperatures and longer daylight hours.
Introduction
Route 66 is nostalgia made physical. It is neon signs and classic diners and ghost towns where the highway was rerouted and the place never quite recovered. It is Cadillac Ranch and the Painted Desert and the Santa Monica Pier at the end of 2,210 miles. It does not just look like every road movie you have ever seen — it is where they were filmed.
This is the ultimate American motorcycle journey — 16 days from Chicago to Santa Monica, across eight states, on the most famous highway in the world. Guided throughout by EagleRider, the world's largest motorcycle tour company, with motorcycle rental, accommodation, support vehicle and daily route briefings all included.
Highlights include the Cadillac Ranch in Amarillo, the Grand Canyon South Rim, the wild burro ghost town of Oatman, the neon oasis of Las Vegas, and the emotional finish at Santa Monica Pier — the official end of Route 66.
Choose how you want to ride
Three ways to take this ride
Discover
The legendary Mother Road — 2,210 miles from Chicago to Santa Monica through 8 states. Cadillac Ranch, Grand Canyon, Oatman and the Santa Monica Pier. Guided by EagleRider.
Price on enquiry
What’s included
- Motorcycle rental for 15 riding days
- 15 nights hotel accommodation
- Welcome dinner in Chicago
- Professional EagleRider Tour Guide
- Daily route briefings and support vehicle
- Route 66 Centennial event access (Tulsa)
Free editorial discovery — no paid route pack or GPX download.
Route overview
The full route
The interactive route map will appear here once daily waypoints are published.
Day by day
Day-by-day itinerary
Welcome to the Windy City! Nicknamed the 'Paris of the Prairie', Chicago is the biggest and most exciting of the Great Lake cities. It includes a stunning skyline along Lake Michigan, and a gamut of top-rated museums, restaurants and cafes. Arrive, settle into the tour hotel, and meet your fellow riders and Tour Guides at the Orientation Meeting before the Welcome Dinner.
Hotel
Chicago, IL — tour hotel in the heart of the city
The riding
What the riding is like
Road types
Difficulty
Moderate
Weather
April to October is the ideal window. Avoid July and August in the desert states (AZ, NM, TX) where temperatures regularly exceed 40°C. May, June and September offer the best balance of comfortable riding temperatures and longer daylight hours.
Riding experience
Intermediate
Bike suitability
Cruiser or touring motorcycle — Harley-Davidson, Indian or Honda Gold Wing. Provided as part of the EagleRider guided package.
When to go
Best time to ride
April to October is the ideal window. Avoid July and August in the desert states (AZ, NM, TX) where temperatures regularly exceed 40°C. May, June and September offer the best balance of comfortable riding temperatures and longer daylight hours.
Ride ready downloads
Take it with you
Downloads will be available here once the Ride Ready pack is published.
Trust & disclosure
Who made this, who runs it
- Route created and researched by The Road Ahead.
- Not yet ridden and verified by The Road Ahead — the route is researched, not confirmed on the road.
- Guided and self-guided packages are operated by EagleRider. You book directly with the operator.
- The Road Ahead may receive a commission or referral fee from partner bookings, at no cost to you.