14 Days • 13 Nights
Route 66: Chicago to Los Angeles
Tour Includes
About the Trip
Trip Highlights
- The full 'Mother Road' from Chicago to LA
- Classic diners, neon signs and vintage motels
- The Route 66 heartland of Oklahoma and Texas
- The deserts and Native lands of the Southwest
- A Grand Canyon detour
- The palm-lined finish at Santa Monica Pier
Day by Day
A detailed day-by-day plan for this 14-day journey.
Met at the airport and transferred to your downtown hotel. Explore the Magnificent Mile and Millennium Park, the starting point of Route 66, and enjoy a welcome dinner of Chicago deep-dish.
Collect your car and hit the road, following Route 66 south through Illinois to St Louis, Missouri, gateway to the West, crowned by the soaring Gateway Arch on the Mississippi.
A day on the road across Missouri and into Oklahoma, passing classic Route 66 towns, roadside oddities and diners, to Oklahoma City.
A day exploring the Route 66 heartland around Oklahoma City, its museums, murals and preserved stretches of the old road, with time for its cowboy heritage.
You drive west into the Texas Panhandle to Amarillo, home of the quirky Cadillac Ranch and the wide horizons of the Great Plains.
Crossing into New Mexico, the landscape shifts to high desert and adobe as you reach Santa Fe, an artsy, historic city of galleries, pueblo architecture and superb southwestern food.
A day exploring Santa Fe's plaza, adobe churches, art galleries and Native American markets, one of the most distinctive and beautiful cities in the USA.
A long, scenic day driving through the deserts and Native lands of New Mexico and Arizona, past the Petrified Forest, to the mountain town of Flagstaff.
A day trip north to the South Rim of the Grand Canyon, standing on the edge of one of the world's natural wonders, before returning to Flagstaff.
You follow one of the longest preserved stretches of Route 66 through classic towns like Seligman and Kingman, sleeping in a vintage desert motel.
The final leg across the Mojave Desert and into California brings you to Los Angeles and the palm-lined Santa Monica Pier, the end of Route 66 at the Pacific.
A guided tour of LA's icons, Hollywood, the Walk of Fame, Beverly Hills and the beaches, celebrating the end of your cross-country journey.
A free day to enjoy LA, the beaches of Malibu and Venice, the theme parks, or the museums and boutiques, ending with a farewell dinner.
After breakfast you return your car and transfer to LA airport for your onward flight, having driven the length of the Mother Road.
Where You Will Travel
What's inside the package?
Inclusions
- 13 nights accommodation
- Daily breakfast, a welcome dinner and a Grand Canyon lunch
- Airport transfers
- Touring, sightseeing and activities as per itinerary with expert guides
- Ground transport, rail or car hire as specified
- National park and attraction entry fees as per itinerary
- a self-drive vehicle for the full route, a detailed Route 66 road book and a Grand Canyon visit
Exclusions
- International airfare
- Visa or tourist card fees where applicable
- Travel insurance (strongly recommended)
- Fuel, tolls and parking
- One-way car hire drop-off fee (advised at booking)
- Meals not mentioned in the itinerary or inclusions
- Drinks unless specifically stated
- Optional excursions and experiences
- Personal expenses and gratuities
- Anything not specifically mentioned under Package Inclusions
Know when to go.
- Visa & ESTA: Visa Waiver Program travellers (including UK, EU, Australian and many others) need an approved ESTA authorisation before flying; other nationalities need a US B-2 visitor visa. A passport valid for the duration of your stay is required, and we advise you based on your nationality
- Currency & cards: The currency is the US Dollar and cards are accepted virtually everywhere; carry a little cash for tips and small vendors. Prices are usually shown before sales tax, which is added at the register
- Tipping: Tipping is an essential part of US culture and service staff rely on it; budget around 18 to 20 percent in restaurants, and tips for guides, drivers, bartenders and hotel staff, which are not included unless stated
- Distances & getting around: The USA is vast, so itineraries combine domestic flights, rail and self-drive; if driving, remember Americans drive on the right, and we arrange car hire, transfers or flights as needed
- Best time to visit: Timing depends on the region; summer suits the northern parks and coasts, autumn brings spectacular colour to the East, spring and autumn are ideal for the deserts and cities, and winter suits the south and skiing
- Health & insurance: No vaccinations are required, but US healthcare is very expensive, so comprehensive travel insurance is essential. Bring any prescription medicines in their original packaging
- Age & ID rules: The legal drinking age is 21 and photo ID is required to buy alcohol or enter bars regardless of age; some car-hire firms add fees for drivers under 25
- Power & connectivity: Power is 120V with type A and B plugs, so bring an adapter; wifi is widespread, and a US eSIM or roaming plan keeps you connected on the road
Frequently Asked Questions
How much driving is involved each day?
This is a true road trip, so several days involve four to six hours of driving, broken up by classic Route 66 stops, diners and sights. The journey itself is the experience, and we pace it with rest days in key cities.
Is there a one-way car hire fee?
Because you collect the car in Chicago and drop it in Los Angeles, there is usually a one-way drop-off fee, which we advise on at the time of booking and include in your quote.
What meals are included?
Daily breakfast is included on most nights, along with any meals named in the itinerary such as a welcome dinner. America's dining is a highlight in itself, so most lunches and dinners are left free so you can explore, with recommendations from us.
How do we get around such a large country?
We combine the most efficient options for your route, domestic flights for long hops, scenic rail where it shines, and self-drive or private transfers for touring. Everything is arranged and built into your itinerary.
Do I need an ESTA or visa?
Visa Waiver Program travellers need an approved ESTA before flying; other nationalities need a US visitor visa. We confirm exactly what you need for your nationality when you book.
When is the best time to travel?
It depends on the regions in your itinerary, summer for the northern parks, autumn for East Coast colour, spring and autumn for the deserts and cities, and winter for the south. We will advise the best timing for your chosen route.
Is tipping really expected?
Yes — tipping is a genuine part of US culture and service staff rely on it. Budget around 18 to 20 percent in restaurants and tips for guides and drivers; we brief you fully so there are no surprises.
Can the itinerary be customised?
Absolutely. We can adjust the cities, parks and regions, change the pace, mix self-drive with flights and rail, and tailor hotels to your interests and budget. Every itinerary is a starting point.
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