Route 66 Road Trip Guide

A Route 66 road trip is one of the most famous USA fly drive holidays.

Chicago to Santa Monica. Diners, motels, neon signs, small towns, desert roads, roadside attractions, old petrol stations, classic Americana and that proper open-road feeling. It’s the road trip people have heard of even if they don’t know exactly where it goes.

Route 66 is iconic, but it is not automatically the best USA road trip for everyone. It’s less about dramatic scenery every single day and more about history, nostalgia, quirky stops, old towns, big distances and the romance of following one of America’s most legendary roads.

In this guide, I’ll cover the classic Route 66 road trip route, how long you need, where to stop, when to go, what it might cost, common mistakes to avoid and whether Route 66 is genuinely the right road trip for you.

If you are not sure whether Route 66 is the right American road trip for you, my USA Fly Drive Guide compares it with California, the national parks, Florida, New England and the Deep South.

Why Choose Route 66 for a Road Trip?

Route 66 originally ran from Chicago to Santa Monica, crossing eight states and covering around 2,400 miles. Along the way, it passes through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. That gives you a huge variety of landscapes and experiences.

You’ll go from big city Chicago to Midwestern towns, roadside diners, old motels, Route 66 museums, open plains, New Mexico desert scenery, Arizona canyons and eventually the California coast.

Some people drive the full route, while others choose a shorter section if they don’t have enough time for the whole thing.

Route 66 is about stopping in places you may never have heard of, seeing the old signs, eating in classic diners, visiting roadside oddities, chatting to locals and enjoying the slower, slightly more nostalgic side of America.

The key is knowing what you’re signing up for. If you expect non-stop Grand Canyon scenery for two weeks, you will be disappointed. If you want diners, desert roads, small towns, vintage Americana and a route with real history behind it, Route 66 can be brilliant. This is where I can help you decide whether it’s the right USA fly drive for your travel style, budget and dates.

Is Route 66 Good for a First USA Road Trip?

A Route 66 road trip can be a fantastic first USA fly drive if you like the idea of a proper long-distance journey. It suits people who want the experience of crossing America, not just ticking off the most famous tourist sights. But it is not the easiest first USA road trip.

It’s more about the story of the road than one famous stop after another. Some days are brilliant. Some days are long. Some places feel wonderfully nostalgic. Others feel like time moved on and forgot to tidy up after itself.

Best Route 66 Road Trip Itinerary

The classic Route 66 road trip route runs from Chicago to Santa Monica.

Chicago → St Louis → Springfield → Tulsa → Oklahoma City → Amarillo → Santa Fe → Albuquerque → Flagstaff → Grand Canyon → Las Vegas → Los Angeles / Santa Monica

Strictly speaking, Las Vegas and the Grand Canyon are not directly on the original Route 66. But for many UK travellers, they make sense as add-ons.

If you’ve flown all the way to the American West and you’re within reach of the Grand Canyon, it would be rude not to at least take a cheeky look.

The classic route gives the trip a clear beginning, middle and end. You start in Chicago, collect your hire car when you’re ready to leave the city, then follow the road west through the Midwest, plains, desert landscapes and eventually into California.

I’d usually recommend driving Route 66 from east to west. That way, the scenery tends to build as you go. You start with Chicago and the Midwest, then move into the wide-open landscapes of Texas, New Mexico, Arizona and California before finishing at the Pacific Ocean.

This is where I can help recommend the right version based on your dates, budget and pace. Sometimes the best Route 66 road trip is the full thing. Sometimes it’s a carefully chosen section with better stops and less driving.

Classic 14-Night Route 66 Road Trip Itinerary

For the full Route 66 road trip, I’d usually recommend at least two weeks. Even then, it will be busy.

Stop	Suggested Stay	Why Go
Chicago	2 nights	Architecture, food, music, museums and the official start
St Louis	1 night	Gateway Arch, blues, barbecue and Mississippi River history
Springfield / Route 66 stop	1 night	Classic roadside Americana and smaller-town stops
Tulsa or Oklahoma City	2 nights	Route 66 history, museums, food and music
Amarillo	1 night	Cadillac Ranch and big open-road scenery
Santa Fe	2 nights	Adobe architecture, galleries, food and New Mexico culture
Albuquerque	1 night	Route 66 neon, Old Town and desert scenery
Flagstaff	2 nights	Route 66 charm and access to the Grand Canyon
Las Vegas	2 nights	Optional add-on for hotels, shows, dining and desert contrast
Los Angeles / Santa Monica	2 nights	Pacific finish, Santa Monica Pier and final Route 66 moment

This gives you a full Route 66 experience with some sensible add-ons, but it is still a moving holiday. You will change hotels often. You will drive a lot. You will see plenty.

Fourteen nights can work, but 18 to 21 nights gives Route 66 far more breathing room, especially if you want to include the Grand Canyon, Las Vegas or extra time in California.

Chicago

Chicago is the classic place to begin a Route 66 road trip.

Chicago’s downtown is known as the Loop, named after the elevated “L” train tracks that run above the streets and loop around the city centre. It’s a great area to explore before starting Route 66 properly, with skyscrapers, theatres, the Chicago River, Millennium Park, restaurants and some brilliant architecture all close together.

Because of the loop, there’s no need to collect your hire car straight away. A car in Chicago is more of a burden than a benefit, and there’s no great romance in paying for it to sit expensively in a hotel garage while you walk around looking at buildings.

The official Route 66 start sign is in downtown Chicago, and while it’s only a sign, it does give the trip a proper beginning.

Once you’ve had time to enjoy the city, you can collect the car and start heading south-west. This is where the journey begins properly.

St Louis

St Louis is a natural early stop on a Route 66 road trip.

The Gateway Arch is the obvious landmark, and the city also gives you Mississippi River history, blues music, barbecue, neighbourhoods, breweries and a very different feel from Chicago.

It works well as a one-night stop if you’re following the classic route west.

Springfield and Classic Route 66 Stops

One of the joys of Route 66 is that some of the best stops are not big-name cities.

Springfield gives you classic Route 66 nostalgia, small-town Americana and, disappointingly, no confirmed sightings of Homer Simpson. Or a nuclear power plant, for that matter.

Small towns, old petrol stations, roadside diners, murals, classic motels and Route 66 museums all form part of the experience.

Tulsa and Oklahoma City

Oklahoma is one of the strongest Route 66 states. It has a huge amount of Route 66 history, with classic roadside stops, museums, murals, restored petrol stations, diners and long stretches where the old road still feels alive.

Tulsa has become one of the more interesting stops on the route, with Art Deco architecture, music history, restaurants and a growing Route 66 identity.

Oklahoma City adds museums, food, history and a bigger city stop before the route continues west towards Texas.

You could stay in either Tulsa or Oklahoma City, or split the time if you want a slower pace.

This is where route planning matters. Some travellers want to follow the old Route 66 alignments as closely as possible. Others prefer a more practical version that mixes classic stops with sensible drive times and better hotels.

Amarillo

Amarillo gives you big skies, wide roads, Cadillac Ranch, steakhouse folklore, Route 66 nostalgia and that unmistakable feeling that you are now very much in the middle of America.

Cadillac Ranch is the famous stop: a row of half-buried Cadillacs covered in layers of spray paint.

Amarillo works well as a one-night stop between Oklahoma and New Mexico. You don’t need to overcomplicate it. Arrive, see the key sights, have dinner, sleep, and continue west.

Santa Fe

Santa Fe is one of the best stops on a Route 66 road trip. It’s not on every modern version of the route, but I think it’s well worth including if you have the time.

The city has adobe architecture — those distinctive earthy, sun-baked clay buildings you often see in the American Southwest — along with galleries, excellent food, Native American and Spanish influences, historic streets and mountain scenery.

After several days of diners, highways and roadside Americana, Santa Fe gives the trip a different flavour. Literally.. the food is superb.

I’d usually recommend two nights here if the itinerary allows. It gives you time to slow down, wander properly, eat well and enjoy somewhere that feels like more than just a stopover.

Albuquerque

Albuquerque is another important New Mexico stop, with Route 66 neon, Old Town, desert scenery, food, museums and easy access to wider New Mexico experiences.

It works well as a one-night stop after Santa Fe or as a longer stay if you want to explore more of the area. The city has a strong Route 66 identity, especially along Central Avenue, where you’ll still find signs, motels and that old road atmosphere.

Flagstaff and the Grand Canyon

Flagstaff is one of the best places to stop in Arizona on a Route 66 road trip. It has a proper Route 66 feel, a walkable downtown, breweries, diners, mountain air and a useful location for exploring the Grand Canyon.

The Grand Canyon is not technically on Route 66, but most people include it. It’s around a 90-minute drive from Flagstaff to the South Rim, which is usually the best option for most first-time visitors. It has the most accessible viewpoints and good accommodation options.

I’d recommend two nights in Flagstaff or near the Grand Canyon if you want to include it properly. That gives you time to drive up, see the viewpoints, maybe catch sunrise or sunset, and avoid treating one of the world’s greatest natural landmarks as a quick photo stop.

Many travellers add the Grand Canyon or Southwest scenery to Route 66, and my USA National Parks Road Trip Guide explains how those landscapes can become the main focus.

Las Vegas Add-On

Las Vegas can work well as an add-on to a Route 66 road trip.

It is not part of the original route, but it makes practical sense for many itineraries because it sits within reach of Arizona, the Grand Canyon and the wider Southwest.

Some people use Las Vegas as a fun break before continuing to California. Others finish the Route 66 section around Arizona and add a few nights in Vegas before flying home or flying onward.

Los Angeles and Santa Monica

Santa Monica is the classic end point of Route 66. After weeks of highways, diners, desert roads, cities and small towns, reaching the Pacific Ocean gives the trip a proper finish.

The Santa Monica Pier is the symbolic end of the road, and yes, you’ll probably want the photo. You’ve earned it.

Los Angeles itself can be added for Hollywood, Beverly Hills, Santa Monica, Venice Beach, film studios, Malibu, museums, shopping and a few final nights before flying home.

The key with Los Angeles is choosing the right area to stay.

LA does not have one simple centre. Santa Monica, Venice, West Hollywood, Beverly Hills, Hollywood and Downtown LA all offer very different experiences.

If you’re ending a Route 66 road trip, I’d usually lean towards Santa Monica or somewhere that gives the trip a more relaxed finish by the coast. If you like the idea of finishing in California but not the full Route 66 journey, my California Road Trip Guide may be a better fit.

How Long Do You Need for Route 66?

For the full Route 66 road trip, I’d recommend 14 to 21 nights.

Duration	Best For
7 nights	A short section only, not the full route
10 nights	A faster partial Route 66 experience
14 nights	Full route at a busy but workable pace
18–21 nights	Full route with better pacing and key add-ons
3 weeks+	Full Route 66 with Grand Canyon, Las Vegas and extra California time

Seven nights is too short for the full Route 66.

Ten nights can work for a selected section, but I wouldn’t recommend trying to drive Chicago to Santa Monica in that time.

Fourteen nights is possible for the full route, but it will be a moving holiday with frequent hotel changes.

Eighteen to twenty-one nights is much better if you want time to enjoy the stops, add the Grand Canyon, spend a little longer in New Mexico or finish properly in California.

If you love the idea of driving, stopping, moving on and collecting little experiences along the way, Route 66 works beautifully.

If you want long stays, dramatic scenery every day and plenty of pool time, another USA road trip may suit you better.

When Is the Best Time for a Route 66 Road Trip?

The best time for a Route 66 road trip is usually spring or autumn.

Spring can work well, with comfortable temperatures in many areas and generally good conditions for driving and sightseeing.

Autumn is also excellent, especially if you want to avoid the worst summer heat in the desert sections.

Summer is popular, especially for school holiday travel, but it can be very hot in places like Texas, New Mexico, Arizona, Nevada and California. It can still work, but you need to plan carefully, start early on longer days and be realistic about how much exploring you’ll want to do in the heat.

Winter is possible, but weather can be more unpredictable. Some sections may be cold, and you could encounter snow or ice in certain areas, particularly around higher elevations.

The best month depends on your priorities: weather, school holidays, budget, events, crowds or how much time you can take away. Tell me what matters most and I’ll recommend the Route 66 itinerary and travel dates that make the most sense.

Route 66 Road Trip Cost

Route 66 can offer good value compared with some USA road trips, but the cost still varies a lot.

As a rough guide, a two-week Route 66 road trip for two adults from the UK might look like this:

Style	Typical Price Per Couple
Good-value	£5,500–£7,500
Mid-range	£7,500–£10,500
Luxury	£10,500–£16,000+

When you book through me, I’ll look at the full picture: flights, car hire, hotel locations, driving times, one-way fees, parking, key stops and the experiences that are actually worth paying for.

Because Route 66 usually involves a longer trip and one-way car hire, my How Much Does A USA Road Trip Cost? guide is worth reading before you set a budget.

Common Route 66 Road Trip Mistakes

A Route 66 road trip is brilliant, but it does need a bit of sensible planning.

Common mistakes include:

• Trying to do the full route too quickly
• Not allowing time for roadside stops
• Underestimating how tiring long drives can be
• Adding too many extras
• Choosing Route 66 because it’s famous, not because it suits you

That last one is important. Route 66 is iconic, but it is not automatically the best USA road trip for every traveller.

My Advice

My honest advice? Don’t choose Route 66 just because you’ve heard of it.

A Route 66 road trip is not just a list of famous landmarks. It’s a slower, quirkier, more nostalgic way to experience America. The magic is in the diners, the motels, the signs, the small towns, the desert roads and the feeling of moving steadily west.

When you book through me, I’ll recommend the best Route 66 road trip itinerary for your budget, travel dates and travel style. I’ll book the flights, arrange the car hire, suggest the best hotel options, check the timings and make sure the whole USA fly drive works properly.

Ready to Plan Your Route 66 Road Trip?

If you’re thinking about a Route 66 road trip, getin touch and I’ll help plan and book a tailor-made USA fly drive holiday that fits your budget, travel dates and travel style.

Whether you want the full Chicago to Santa Monica route, a shorter Route 66 section, a Grand Canyon add-on, a Las Vegas stop or a more relaxed California finish, I’ll recommend the best route, sort the details and make sure the whole trip works properly.

Preferably with fewer browser tabs, fewer heroic driving days and no accidental attempt to cross America in a week because “it didn’t look that far on the map.”

Continue Planning Your USA Road Trip

If you’re still researching, these guides will help:

• USA Fly Drive Guide — the complete overview of routes, timings and planning advice
• How To Plan A USA Fly Drive Holiday — practical advice on flights, hotels, car hire and route planning
• How Much Does A USA Road Trip Cost? — realistic budgets and where the hidden extras appear
• Best USA Road Trips For First-Timers — compare Route 66 with California, Florida, New England, the Deep South and the national parks

 

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