Route 66 isn't really about getting from Santa Monica to Chicago. It's about everything that survives between them.
Old gas stations. Neon motel signs. Diners that have been flipping burgers for generations. Main streets bypassed by the interstate. Giant roadside attractions that make absolutely no sense until you're standing underneath one.
Two weeks is often recommended for a Route 66 road trip, and three would give you considerably more time to explore. We had 11 days, which proved enough to experience the full route without turning every day into an endurance drive.
It did mean making choices. We couldn't visit every museum or stop at every historic gas station. Some towns received a few hours; others got little more than lunch and a walk around.
We were fine with that.
Route 66 is one of those journeys where sometimes the places you didn't plan to stop become the ones you remember most.
Day 1: Santa Monica to the Mojave Desert
There could hardly be a more dramatic starting point.
We began beside the Pacific at Santa Monica Pier, standing beneath the famous Route 66 End of the Trail sign before walking back towards our RV.
Except for us, it wasn't the end.
It was mile zero.
Los Angeles gradually disappeared behind us as we headed inland, trading palm trees and coastal air for mountains, desert and increasingly enormous skies.
This first day was partly about finding our rhythm. An RV sounds romantic until you're manoeuvring one through Southern California traffic, but once the city thinned out, everything changed.
This was what we'd come for.
Into the Mojave
By the time we reached the Mojave, Route 66 had started to look more like the America we'd pictured before the trip.
Long stretches of road disappeared towards the horizon. Freight trains rolled alongside us. Old businesses appeared almost from nowhere and vanished just as quickly in the mirrors.
We passed through Barstow, one of the classic Californian Route 66 towns, and continued onto sections of the old highway where the interstate suddenly felt a very long way away.
There was no need to fill the afternoon with attractions.
The desert was the attraction.
Day 2: California to Arizona via Oatman and Kingman
If Day 1 introduced us to Route 66, Day 2 was when we really fell for it.
We continued east towards the Arizona border before turning towards Oatman, an old mining town in the Black Mountains that has somehow become equally famous for the wild burros wandering its streets.
Calling Oatman unusual doesn't quite cover it.
Old western-style buildings line the main street, burros casually wander between visitors, and the road approaching town twists through a landscape that feels completely removed from the modern interstate nearby.
From Oatman, we continued to Kingman, one of Arizona's best-known Route 66 stops, before following the old road towards Seligman.
Seligman: Where Route 66 Refuses to Die
Seligman is gloriously over the top.
Vintage cars, old signs, mannequins, neon, souvenir stores and Americana spill along the roadside. If you've come searching for subtlety, you've taken the wrong road.
But there's a reason the little town has become such an important stop on Route 66.
This is exactly the sort of place that fought to keep the road's identity alive after Interstate 40 bypassed many of its communities.
We wandered, took far too many photos and eventually continued east towards Flagstaff, watching the desert scenery gradually give way to pine forest.
It was hard to believe we were still in Arizona.
Day 3: Flagstaff, Winslow and the Petrified Forest
We left Flagstaff early and headed east.
One of our first stops was Winslow, a town that has turned a single line from an Eagles song into an entire attraction.
Yes, we stood on the corner. Of course we did.
From there, the landscape opened up again as we continued towards Petrified Forest National Park.
Petrified Forest National Park
This was one of the places we deliberately gave more time.
The park protects an extraordinary landscape of colourful badlands, desert and enormous deposits of petrified wood, with Route 66 once cutting directly across the area.
After days of diners, signs and roadside Americana, it was a reminder that some of the greatest sights on Route 66 have nothing to do with the road at all.
By late afternoon we were heading towards the New Mexico state line and Gallup, with another state behind us and a completely different landscape ahead.
Day 4: Gallup to Albuquerque and the Neon of Tucumcari
New Mexico was one of our favourite sections of the entire Route 66 road trip.
There is something about the combination of desert, mountains, adobe architecture and enormous skies that makes driving here particularly good.
We headed east from Gallup towards Albuquerque, where historic Route 66 cuts straight through the city along Central Avenue.
This was one of the occasions when travelling in an RV was useful. We could stop, wander for a while, grab something to eat and continue whenever we felt ready.
But our real target for the evening was farther east.
Tucumcari After Dark
If there is one Route 66 town worth arriving in after sunset, it's Tucumcari.
During the day, it can feel sleepy.
At night, the neon comes alive.
Old motel signs glow beside the highway, including some of the most recognisable surviving neon on Route 66. It feels less like someone has recreated the 1950s and more like nobody remembered to turn the lights off.
We slowed down and took our time driving through town.
Four days into the journey, this was the Route 66 we'd hoped still existed.
Day 5: New Mexico to Texas and Cadillac Ranch
We crossed into Texas with one destination already firmly on the list.
Cadillac Ranch is ridiculous.
Ten Cadillacs buried nose-first in a field outside Amarillo shouldn't be one of America's great roadside attractions. And yet, somehow, it works.
We pulled over, walked out into the field and joined generations of Route 66 travellers who have stopped here to photograph and spray-paint the cars.
Amarillo and the Texas Panhandle
Amarillo gave us another dose of oversized Route 66 Americana.
The Big Texan Steak Ranch is perhaps best known for its infamous 72-ounce steak challenge, but even if you have absolutely no intention of attempting it, the place is worth seeing.
Everything is big, loud and unapologetically Texan.
Later we continued east through the Panhandle towards Shamrock, where the beautifully restored art deco U-Drop Inn looks like something designed for a movie set.
Except it has been standing beside Route 66 since the 1930s.
Day 6: El Reno, Oklahoma City and Tulsa
Oklahoma has more driveable miles of historic Route 66 than any other state, so this was never going to be a day for simply jumping onto the interstate.
And there was one particular town we wanted to drive through hungry.
An Onion Burger in El Reno
El Reno is synonymous with Oklahoma's fried onion burger.
The dish emerged during the Depression era, when onions were an inexpensive way to stretch ground beef further. What started out of necessity became a local institution.
We stopped at Sid's Diner, where patties hit the griddle beneath a mound of thinly shredded onions until beef, onion and all those caramelised edges essentially become one glorious mess.
It wasn't sophisticated, but it was excellent.
And sitting in a small-town Oklahoma diner eating a fried onion burger might have been one of the most authentically Route 66 meals of the trip.
From El Reno, we continued through Oklahoma City before heading northeast towards Tulsa.
Route 66 Through Tulsa
Tulsa feels different from many of the smaller Route 66 communities we'd passed through.
There's plenty of history here, but also a new generation embracing the road rather than simply preserving it.
We explored sections of the historic route, found more neon, passed the enormous Golden Driller and stopped by the wonderfully bizarre Buck Atom's Cosmic Curios before eventually calling it a day.
Tomorrow we'd cross an entire state in a matter of minutes.
Day 7: Three States and One Night at the Wagon Wheel Motel
Leaving Tulsa, we headed northeast and eventually crossed into Kansas, where Route 66 spends only around 13 miles. That makes Kansas easy to dismiss, but that would be a mistake.
The road passes through Galena, Riverton and Baxter Springs, a tiny slice of southeastern Kansas filled with the sort of old buildings, service stations and small-town character we'd increasingly learned to appreciate.
Before long, we crossed into Missouri.
Springfield, Missouri
We made our way through Springfield, a city with a particularly strong claim to Route 66 history. It was here in 1926 that officials proposed the number “66” for the new Chicago-to-Los Angeles highway.
But we weren't staying in Springfield.
There was somewhere farther along the road we'd been looking forward to since California.
We Parked the RV for the Wagon Wheel Motel
For most of the journey, our RV had been both transport and accommodation.
Tonight, we abandoned it.
In Cuba, Missouri, we parked the RV and checked into the Wagon Wheel Motel, one of the great surviving icons of Route 66.
The motel dates back to the 1930s, with stone cottages arranged around its famous neon sign. It's the kind of place that could so easily have disappeared when travellers moved onto the interstate, yet somehow survived.
After seven days of carrying our bedroom around America with us, sleeping in a proper Route 66 motel felt strangely luxurious.
More importantly, it felt right.
If you're going to drive the Mother Road, you should spend at least one night beneath the glow of an old neon motel sign.
Day 8: Cuba to St. Louis
We woke in Cuba and took a little time to explore before continuing towards St. Louis.
Cuba itself is known as Route 66 Mural City, with large murals scattered around town telling stories from the area's history.
Then the road pulled us towards the biggest city we'd seen for several days.
St. Louis and the Gateway Arch
Seeing the Gateway Arch rise into view felt like another milestone.
We'd crossed the deserts of California and Arizona, New Mexico, the Texas Panhandle, Oklahoma and the tiny Kansas stretch.
Now we were unmistakably in the Midwest.
We explored St. Louis, sought out sections of historic Route 66 and made time for another local institution: frozen custard at Ted Drewes.
By this stage of the trip, we'd realised that food stops were becoming almost as effective at charting our progress across America as state lines.
Day 9: St. Louis to Springfield, Illinois
Crossing the Mississippi River brought us into Illinois, our eighth and final state.
Chicago was getting close.
But Illinois contains one of the most rewarding stretches of Route 66, particularly if you resist the temptation to simply race north.
Small towns, restored filling stations, giant roadside characters and old diners appear regularly along the historic route.
We headed for Springfield, Illinois' state capital and a city inextricably linked with Abraham Lincoln.
A Cozy Dog on Route 66
For lunch, there was really only one choice.
Cozy Dog Drive In has been serving its famous hot dogs on sticks to Route 66 travellers for generations.
It was quick, unpretentious and exactly the sort of lunch we'd come to love on this trip.
By now we were less interested in finding the “best restaurant” in each city and more interested in eating somewhere that belonged to the road.
There's a difference.
Day 10: Springfield to Chicago
Our final driving day began with the strange feeling that we didn't really want to arrive.
For ten days, the next town had always been waiting.
We continued north through Illinois, stopping in Pontiac, one of the most enjoyable Route 66 towns in the state, before following the road towards Joliet.
The landscape became increasingly urban.
Traffic returned.
The enormous skies and empty roads that had defined so much of the journey gradually disappeared.
Chicago was ahead.
Reaching the Beginning of Route 66
And then, suddenly, we'd done it.
We had driven Route 66 from Santa Monica to Chicago.
Historically, the famous highway begins in downtown Chicago near the intersection of Adams Street and Michigan Avenue. For most travellers, it's where the adventure starts.
For us, it was the finish line.
There was something satisfying about ending among skyscrapers after beginning beside the Pacific Ocean.
Behind us were approximately 2,500 miles of America.
Eight states.
Desert highways and Midwestern main streets. Neon motels. Onion burgers. Cadillac Ranch. Wild burros. Petrified forests. Tiny Kansas towns. An RV that had somehow become home.
We parked it.
For once, there was nowhere else we needed to drive.
Day 11: Chicago and the End of Our Route 66 Road Trip
We deliberately kept our final day free.
No RV miles. No rushing towards another state line. No roadside attraction 80 miles down the highway that we absolutely had to see.
Just Chicago.
After ten days watching towns appear and disappear through a windscreen, being able to walk around felt surprisingly good.
We wandered downtown, explored the lakefront and looked back at the Route 66 sign we'd reached the previous day.
Driving west-to-east had seemed slightly unconventional when we started.
Now we wouldn't have changed it.
Beginning with the Pacific and gradually working our way through deserts, mountains, plains and small-town America before finishing among Chicago's skyscrapers gave the journey a natural crescendo.
Santa Monica felt like the beginning of an adventure.
Chicago felt like we'd crossed a continent.
Is 11 Days Enough for Route 66?
For us, yes.
Would we have found things to do with 14 days? Easily.
Could we have spent three weeks exploring every museum, historic filling station, roadside attraction and small town? Absolutely.
But 11 days was enough to drive Route 66 without feeling as though the entire trip happened through the windscreen.
There were long driving days. There were attractions we skipped. There were towns where we stayed for hours and others where we barely stopped.
That's part of a road trip.
If you have less than 10 days, we'd seriously consider tackling only part of Route 66 rather than rushing the entire thing. With around 10 to 14 days, however, driving the full route becomes much more enjoyable.
Our 11-Day Route 66 Itinerary
For anyone planning a similar Route 66 road trip, this is roughly how our journey unfolded:
Day 1: Santa Monica → Barstow and the Mojave Desert
Day 2: Barstow → Oatman → Kingman → Seligman → Flagstaff
Day 3: Flagstaff → Winslow → Petrified Forest → Gallup
Day 4: Gallup → Albuquerque → Tucumcari
Day 5: Tucumcari → Amarillo → Shamrock
Day 6: Shamrock → El Reno → Oklahoma City → Tulsa
Day 7: Tulsa → Kansas → Springfield → Cuba
Day 8: Cuba → St. Louis
Day 9: St. Louis → Springfield, Illinois
Day 10: Springfield → Pontiac → Joliet → Chicago
Day 11: Chicago
It's a relatively fast Route 66 itinerary, but one we'd happily do again.
What Was It Like Driving Route 66 in an RV?
An RV turned out to be a brilliant way to experience Route 66.
We weren't tied to hotel check-in times, and we had somewhere to make coffee, grab food or simply stop for a while whenever the road got long.
More importantly, it suited the spontaneity of Route 66.
See an old sign? Pull over.
Find a strange roadside attraction that wasn't on the itinerary? Stop.
Want to stay somewhere longer than expected? You can.
There are practical considerations, of course. An RV isn't nearly as easy to manoeuvre through Los Angeles or downtown Chicago as a car, and some older sections of Route 66 require a little more planning.
But once we reached the open road, it made perfect sense.
Ironically, one of our favourite nights was the one night we deliberately left it parked outside and checked into the Wagon Wheel Motel.
The Best Stops on Our Route 66 Road Trip
Asking us to pick one favourite would be difficult, because Route 66 isn't really defined by one blockbuster attraction.
But a few experiences stood above the rest.
Oatman was one of the strangest and most entertaining towns we visited. Tucumcari after dark delivered the neon Route 66 we'd imagined before leaving home. Petrified Forest National Park provided some of the most spectacular landscapes of the journey. El Reno gave us one of its most memorable meals. Cadillac Ranch was every bit as weird as expected.
And spending a night at the Wagon Wheel Motel in Cuba gave us something an RV couldn't: the experience of actually sleeping inside a piece of Route 66 history.
But some of our favourite memories were smaller than that.
An empty road disappearing into the desert.
Coffee in the RV before anyone else seemed to be awake.
A faded sign advertising a business that had somehow survived another decade.
Watching freight trains run alongside us.
Pulling into towns we'd never previously heard of and wondering what we'd find.
Those were the moments that made Route 66.
Why Route 66 Is Still Worth Driving
Route 66 officially disappeared from the U.S. Highway System in 1985.
Yet somehow, it never really went away.
In 2026, the Mother Road celebrated its 100th anniversary, and perhaps that's the most remarkable part of its story. A highway that technically no longer exists continues to draw travellers from around the world.
After 11 days on it, we understood why.
You can drive faster roads across America. You can fly over the entire thing before lunchtime.
But neither will take you through the America Route 66 reveals.
The old diners and motels matter. So do the neon signs, restored gas stations and wonderfully ridiculous roadside attractions. But what stayed with us most were the communities between them.
Route 66 forces you to leave the interstate, slow down and drive through places most travellers now bypass.
And somewhere between Santa Monica and Chicago, that stopped feeling like the slower way across America.
It became the entire reason for going.
