US Roadtrips

Route 66 – The ultimate American road trip

Route 66: Day 1 Chicago IL to Springfield IL

My Route 66 Road Trip

Driving the route 66 from Chicago to LA has always been a dream of mine. In 2021 since, due to covid restrictions and the status of my green card application, I was not allowed to leave the country, I decided to embark in a 2 weeks epic journey on one of the most iconic road on planet Earth.

That said I haven’t owned a car since leaving Italy in 2006 and, aside from when I took the Illinois driving license test, the last time I was behind a steering wheel was probably Christmas 2018 back at my parent place in Milan. And my experience driving in the US was limited to that time I drove from Miami to Key West and back, a few years before.

But, having moved from London to Chicago in 2019, I must have walked by the Route 66 starting point sign a hundred times. It was now or never: the Mother Road was calling me.

You can either click here to get to the daily posts with all sort on additional info about my trip – where I stayed, what I ate, what I saw – or here if you want to read all the daily postcards in one go. Or just keep scrolling.



Planning the Route 66

Having decided to start the trip June 26, the day of my 48th birthday, I started doing my researches in April or so. I bought a couple of books, including the classic EZ66-GUIDE – that is super interesting and beautiful to have and browse in the evening while planning the following day leg – and a lifesaver app called -unsurprisingly – Route 66 navigation. Maybe not the most romantic way to get around but it proved time and time again to be the only realistic way to stay on the historical Route 66 and to not miss the plethora of attractions spread along the road from IL to CA. A must have IMO.


Route 66: Day 11 Chambers AZ to Sedona AZ


Where does Route 66 start and end?

Route 66 starts in downtown Chicago, Illinois at 78-98 E Adams St, Chicago, IL 60603 and ends at the Santa Monica pier in Los Angeles, California. The midpoint of Route 66 is in Adrian, Texas. It’s exactly 1139 miles from Chicago and 1139 miles from Los Angeles.

How long is a road trip on the Route 66?

Not making any detour, driving on the historic Route 66 from Chicago to Los Angeles means driving for about 2,448 miles. My itinerary was much longer, 3,291 miles to be exact, due to a number of diversions along the route.

How many days does it takes to Drive the historic Route 66?

It took me exactly 14 days, but if you have the time and the money to do so probably 20 days is the sweet number to get all the way from Chicago to Los Angeles seeing most things without killing your back with long, tiring drives.

My two weeks itinerary on the historic Route 66

picked up my car at O’Hare airport – cause it was cheaper than renting downtown – early in the morning and I drove back to the Route 66 begin sign at 78-98 E Adams St, Chicago, IL 60603. From there this was the itinerary (A description, map and general information are in each daily post)




Where do you stay when driving the Route 66?

I stayed mostly in motels, partly to safe costs, partly cause in certain location there were no alternatives, partly cause motels are pretty cool and iconic. Most of the time I felt like I was in a movie. I’ve added the name of the accommodation in each of the daily posts.

How many miles do you need to drive every day and for how many hours?

Thanks for a couple of detours I drove 3,291 miles in total. The longest leg was 429 miles. Considering stops for pictures, gas, food and that you want to drive the historic route not the new highway, you might expect to stay on the road for up to 8h every day

How much does it cost to drive the Route 66?

Driving the historic Route 66 is a one in a lifetime experience but it doesn’t come cheap: It costed me a bit short of $5,000 in 2021 (excluding gas and food)

  • $3,000 to rent the car in Chicago and return it in Los Angeles – including full insurance
  • $1,600 in lodging
  • $127 for the flight back to Chicago with American Airlines (I live in Chicago so that’s was a cheap one way ticket)

What type of car is best to drive the Route 66?

If your budget in unlimited and the season allows it, obviously a convertible is a dreamy option to drive all the way from Chicago to Santa Monica. That said, I recommend a Midsize SUV for a number of reasons:

The weather. Even assuming you are not thinking to drive the Route 66 in winter, you are gonna cross multiple States and the weather can be unpredictable. I drove it end of June and I hit 2 tornadoes and heavy rain half of the days.

Second: it is a long, long drive. You want to be as comfortable as possible to avoid back and neck-pain. The more stable the car the better it is.

Last but not least: the cost. Unless you want to drive all the way back to Chicago (or to LA depending where you pick up the car) you’ll need a one-way-rental. And that’s expensive for any car. With a convertible the rental price will go up the roof. It would cost you probably 3-4 times more than a SUV. Also remember that you better have a FULL insurance that covers any kind of accidents or issues.

Pro tip: renting the car at the airport – and returning it at the airport – might be much cheaper (plus you have much more options) than renting it downtown. Also book it in advance to avoid disappointments.

Can you drive the Route 66 with an electric car?

I didn’t but yes, you can. You just need a little bit of additional planning to find an EV charger, but along the Route 66 you’ll find tons of opportunities to do so. Tesla Superchargers have been available across the route since 2016 and fast-charging networks such as Electrify America and ChargePoint are available too.


route 66 barstow to santa monica
Driving the Historic Route 66: the last leg in California


Postcards from the Route 66

Day 1: Chicago to Springfield

First 202 miles done. Feat: three flash  flooding alerts, two tornadoes, two weird giants, one delicious hot dog, a number of charming small cities, a glorious sunny entrance into Springfield. An eventful birthday, I say.


Route 66 Chicago to Springfield
Driving the Historic Route 66: first day, 2 tornado alerts. Great start, right?

Day 2: Springfield to Cuba

The weatherman said to expect heavy rains but today I drove 204 miles mostly with blue sky and a beautiful although pretty hot sun.

Notable: never-ending corn fields, long smooth roads, abandoned bars, gas stations and motels, the mighty Mississippi river and me, walking on the Chain of Rocks Bridge, leaving Illinois for the first time in 18 months.


Route 66 Springfield to Cuba
Driving the Historic Route 66: Gateway Arch Monument, St Louis. It was sunny!

Day 3: Cuba to Carthage

Hitting the road before 7am ended up being a great idea since another storm happened minutes after arriving at destination, 255 miles later.
The road, at first rougher and honestly more fun to drive, turned soon into a wave of smooth rolling hills: an hypnotic relaxing up and down lulling, that lasted till the Mother road matched the Highway 96 with its hordes of huge scary trucks. End of the fun.

A few more abandoned premises, big signs and the coolest motel so far, straight out of an action movie.

Edit: dying for a beer to fight the post-rain humidity and this city doesn’t seem to have any bar or store open. Not. Even. One.


Route 66: Cuba MO to Carthage MO
Driving the Historic Route 66: rolling hills between Cuba and Carthage MO

Day 4: Carthage to Oklahoma City

I see a pattern: sun in the morning, rain in the afternoon.
This was one of the longest stretch, 268 miles, so I left with the sunrise to avoid the expected storms in Oklahoma. The electric blue sky and the sleepy traffic were a welcomed companion while driving out of Missouri into Oklahoma via the little pretty Kansas belt.
Oklahoma was long straight roads, one of the weirdest attraction I’ve ever seen, fields and cows.

Till Tulsa.

I guess the suddenly gloomy sky didn’t help but the 70 miles connecting Tulsa to Chandler were something else. No more charming cities, no more memorabilia or well preserved roads. Nothing to remember or celebrate here. The forgotten America.

From that point was just pouring rain and scary growing brown rivers till I reached another sunny finish line in Oklahoma City.


Route 66 Carthage to Oklahoma City
Driving the Historic Route 66: the Blue Whale of Catoosa

Day 5: Oklahoma City to Amarillo

Everything is bigger in Oklahoma: fields, breakfasts, roads. Then you get to Texas where everything is bigger than in Oklahoma. Much bigger.

The drive was great till the outskirts of Amarillo when a new, big ,afternoon storm spoiled the day. Before that, it was a solitary sunny ride for about half of today’s 291 miles: the historical route runs pretty much parallel to the new highway so the big trucks and the non-tourist drivers don’t even bother driving slower on the mother road.

The landscape changes pretty much as soon as you enter Texas: wilder, more barren. You see cowboy hats on oversized pickups and big houses that look like ranches that look like houses. But bigger.

Did I say everything is bigger here?

Note to self: don’t have a late (big) breakfast in a diner in Oklahoma if you are planning a (big) steak night in Texas. Burp.


Route 66: Amarillo Texas
Driving the Historic Route 66: when in Texas…

Day 6: Amarillo to Tucumcari

The shortest and nicest leg so far. 126 easy miles, crossing the midpoint from Chicago to LA, with mostly blue sky and not a drop of rain.
With the desert getting closer, the landscape became more dramatic and the roads a tad more broken.

I probably should stop taking pictures of gas stations, diners and motels signs but they make me smile every single time, I won’t stop.

The motel I am staying has a 60s theme
that makes you feel like putting on your best shiny dancing shoes and hit the city. But Tucumcari is hardly a city and I only have my weared out Converse All Star with me. I guess a New Mexico beer or two while reading on the balcony will be a valid alternative.

Also: “It’s science bitch!


Route 66 Amarillo to Tucumcari
Driving the Historic Route 66: feeling like in a Breaking Bad episode. It’s science bitch!

Day 7: Tucumcari NM to Santa Fe

“That day I was stranded in the middle of nowhere in New Mexico for hours after my car broke down and partly flooded during another impromptu heavy storm. In July.”
A true story to tell laughing around a dry, warm table, drinking wine with friends one day.

The tow truck guy that brought me to Albuquerque told me he has never seen so much rain in New Mexico. I believe him. Even the desert  is greener than normal.

Not many of today’s 236  miles were on the historical route. I’ll make up for it tomorrow driving back a few miles on the Santa Fe loop with the replacement car. Not orthodox but who cares.

From now on it should be dry ( famous last words from the guy that just got drenched with rain walking back to the motel).


Route 66 tucumcari to santa fe
Driving the Historic Route 66: shit happens so you better have a full car insurance… word!

Day 8: Santa Fe NM to Gallup

As planned I took the Route 66 eastbound to catch up with what I missed yesterday (not much in reality) before heading back west towards Albuquerque for a Breaking Bad nostalgia stop and from there further west to Gallup on the external border of the Navajo Nation. It added up to a monster 429 miles. Too much in one day.

From Albuquerque onwards, right after the city borders, the landscape became that familiar, wild, fierce, uninhabited desert, seen in uncountable films and tv series: burned ground, sparse, scattered vegetation, long never-ending roads and an unreal spectacular sky. Like a movie.

Remind to self: sunscreen. Ouch.


Route 66: Albuquerque
Driving the Historic Route 66: Walter White’s house in Albuquerque.

Day 9: Gallup to Bluff

Took a little detour from the Route 66, heading 170 miles north, to southern Utah, via Colorado.
If yesterday was a Breaking Bad kinda landscape, today I drove straight into a western movie set: New Mexico and Colorado boasted the usual long, empty, easy to drive highways, entering Utah the roads got twisted, the rocks closer, the heat higher.

Things I would have never expected to do in my life and I’ve accomplished today:

  • doing a laundry in an empty, ghostly automatic laundromat in the southern Utah desert
  • Celebrating July 4th in a town in Utah with a total population (90) smaller than the population of my building
  • Being in Utah

Also: happy birthday mom.


Route 66: Gallup to Bluff
A first diversion from the Historic Route 66: diving all the way to Bluff, right at the entrance of the Monument Valley

Day 10: Bluff to Chambers

Another early morning and I went back to the Route 66 via an enchanting drive on the Scenic Byway 163 which travels through Monument Valley. The national park was still closed due to COVID concerns but the drive is nonetheless incredible.

311 miles later, 50 of which within the Petrified Forest National Park, a bit further west from my motel, and I am back on the Mother road, in Arizona this time.

I did a couple of miles hike part of which running, to test my Achilles after last month injury. The results are in:

  • The tendon is ok
  • Running in the desert is a very, very bad idea

Forrest Gump Point, Monument Valley
Forrest Gump Point on the Scenic Byway 163, where Forrest stops and says “I’m pretty tired, I think I’ll go home now”

Day 11: Chambers to Sedona

The leg from Chamber to Flagstaff is not particularly interesting with the 140 miles being pretty much all on the highway.
Pro: it is pretty quick.
Exception: the “Here It Is” rabbit is awesome.

From Flagstaff to Sedona (an additional 35 miles detour from the Route 66) everything changes: forget the desert. Pine trees and lush vegetation make you wonder if you have been magically transported to a sunny version of Washington State. Or to the Italian Alps.

Writing from the beer garden of a brewery cause alcohol is not a solution to any of your problems but boy: it damn helps.


Chambers to Sedona
Another diversion from the Historic Route 66: Sedona.

Day 12: Sedona to Kingman

228 miles later I got to the last stop in Arizona. Quite a demanding ride through the desert during the most torrid day so far, with temperatures well over 110F / 43C. Side window open, I refuse to use air-con.

The landscape got more and more harsh and solitary but some new vintage signs and a few unexpected stops in old-time retro diners along the route gave meaning to today’s 7h sauna.

Things I can thick off my to-do list in life:

  • Look at my coffee in the cup holder 16 miles after leaving the motel to realize I have left my luggage in the lobby, next to the coffee machine
  • Have the best hotdog ever + milkshake + root beer in a 60y old diner, in the desert 

Route 66: Day 12 Sedona AZ to Kingman AZ
Back on the Historic Route 66: Seligman, Arizona

Day 13: Kingman to Barstow

241 miles in a oven. I left early to avoid the expected heatwave but it wasn’t early enough.
Today’s leg started with some series of nervous narrow turns, in and out on the mountains leading to the ghost town of Oatman, now a kind of Disneyland for western movie lovers. After that, the Route 66 enters California, skirting the southern part of the Mojave desert and it is just nothingness, lizards crossing the roads and burning temperatures. Kinda beautiful.

One more sleep to the grand finale.


Route 66: Day 13 Kingman AZ to Barstow CA
Driving the Route 66: somewhere between Kingman, Arizona and Barstow, California

Day 14: Barstow CA to Santa Monica

Not too far into the last 155 miles (out of the ~3,291 since I left Chicago) driven today, I started feeling like I was already in a suburb of the City of Angels. Commuters, traffic lights, heavy, slow traffic.

The amount of cars around has been inversely proportional to the number of miles left to arrive in Santa Monica. Such a striking difference from the desolation and never ending spaces of the last few days (Tune: “People so busy, make me feel dizzy…”).

Reaching the end of the road trip has been a bitter sweet moment. Driving the Route 66 was a teenager-me dream. It’s done now. Maybe I just don’t like when things end.

And, in all honesty, I don’t even like driving…

Know what the murals on Sunset boulevard in this pic is (or was, damn gentrification) and you’ll get my unconditional eternal respect


Route 66: Day 14 Barstow CA to Santa Monica CA
Driving the Historic Route 66: the end of the Route


Leave a Reply

Your email address will not be published. Required fields are marked *