Itinerary - Route 66: Road trip from Chicago to LA

Arrive and check-in at your hotel in Chicago. We are in the "Windy City", as Chicago is nicknamed . The wind here is actually a constant - but a little breeze that comes from the immense Lake Michigan , which the city overlooks, certainly doesn't scare us. Let's start exploring the city - with The Bean as our first stop! Then let's have a taste of Chicago's most famous dish… yes, you're right - the deep dish pizza! Will this pizza win us over or will we remain faithful to the original? We will find out!

We have a full day to explore Chicago and all it has to offer. We will take part in a guided tour - for sure the best way to discover the hidden gems of the city. Here, the skyscrapers are plentiful and the skyline decidedly iconic – among the most famous skyscrapers here is the Willis Tower , where you can take a stroll into the void - literally. Yes, in the observatory you can walk on a ledge made entirely of glass more than 400 meters high - definitely not suitable for vertigo sufferers! But if you enjoy a thrill, you will absolutely love this.

After seeing the city from the sky, let's get back down to earth and make another leap to Millennium Park to take a few more selfies in front of the big bean - then we can decide together what to do: we can go to Navy Pier, full of shops and attractions, or pop into one of the many museums. Another option: a mini cruise along the river past the skyscrapers, definitely a different perspective on Chicago! We then return to the hotel to take a quick shower before our first dinner - what will American cuisine offer us?

Finally today begins our real journey on the road : ready to head down Route 66 ? Where can we pick up the cars that will accompany us on the road, if not in Pontiac? We reach this suburb of Illinois which has the same name as that of Michigan where the first factories of General Motors were built, the famous US parent company, among others, of Cadillac and Chevrolet. Time to have the keys in hand, take a group photo in front of the mural that indicates the beginning of Route 66 and finally... we're off! The first kilometers will be the most exciting: we are on the most famous road in the world! We get to grips with the asphalt until we get to the small town of Springfield , the capital of Illinois, where we stop for lunch - grilled cheese everyone?

We take a stroll through Springfield, where President Lincoln also lived (in fact there are statues, murals and museums dedicated to him dotted around) and then we set off again, towards St. Louis , saying goodbye definitively to Illinois and entering the state of Missouri . This city sits along the banks of the longest river in the United States, the Mississippi , and is famed for its blues-related music culture - we've traveled a long way south and already notice the differences from more cosmopolitan Chicago. Let's take a walk around the city, starting from its symbol, the Gateway Arch (the tallest arch in the world) and perhaps choosing a place with live music for tonight.

Good morning America! We wake up early and are ready to hit the road: this morning the road takes us to the heart of Missouri , both figuratively and literally! We move immediately towards Cuba  (no, not the island!), a town full of murals where we can stop for a coffee and then restart the engines and head towards the Meramec caves , impressive caves with spectacular rock formations! We return to the surface and get back on the road, reaching Rolla , where we stop for two reasons: the first, to visit the Totem Pole Trading Post, which is apparently the longest-running business on Route 66 in all of Missouri (established in 1933!); the second, we are hungry! So we stop to eat something - hamburger and fries (and milkshake, in good American tradition)?

You won't believe it, but today we also stop… in Springfield (no no, it's not the same Springfield as yesterday!) After taking a look around, we then set off again to… another state! It seems impossible, but in 3 days we have already crossed two! We reach Galena , famous because here we can see scale reproductions of the famous cars from the film "Cars" - the customary photos are practically obligatory for everyone. We have dinner in this quirky town on the Missouri-Kansas border and then we arrive at the hotel - tomorrow we have a lot of miles to go and new places to see!

In case it wasn't clear: yes, we are traveling along Route 66, but we are also crossing three quarters of the United States, passing through what are perhaps its most eccentric and exciting places. This morning is no different: the first stop is in Catoosa , where we find a… whale ? Yes, a kind of work of art that has become one of the symbols of Route 66 has exactly the shape and appearance of a whale: we stop here and, as always… the ritual selfie! We get back on the road and say goodbye to Kansas, entering the state of Oklahoma - we are pushing further and further west, after having crossed the immense plains that make up the landscape of the centre of the States. There's no shortage of farms here, as well as cornfields - maybe we'll even see aliens? Hanz Zimmer is a must for the playlist.

We stop in Tulsa for a Mexican lunch - as well as going west, we've also moved south, meaning we are now in the land of cowboys, and we realise it in Oklahoma City , the state capital, where there is no shortage of cowboy boots and hats and that strange feeling of being in the middle of a film with Morricone's soundtracks. Here we have to stop in Stockyards City , a real western "village" where we can find everything - will any of us buy cowboy boots? We also stop in the city for the evening and take a stroll through the downtown district known as Bricktown - there is no shortage of restaurants here, and for sure we have to try something local. Steakhouses are hugely popular, as are fried chicken and deep-fried pickles - our arteries must be jumping for joy by now.

Another day, another journey: this morning we reach Elk City , where we immerse ourselves in the history of Route 66 by visiting the museum of the same name. Inspired by those who have traveled this famous road before us, which runs from Illinois to California, we're back on the road - today we'll be on the road for lunch, so let's keep our eyes open in case we come across a typical diner that inspires us.

We will continue until we arrive at Shamrock - and yes, we have officially entered Texas ! If we bought cowboy hats or boots yesterday, the time has undoubtedly come to wear them and feel part of the local population! In Shamrock we stop at the U-Drop Inn , an example of art deco applied to a gas station - definitely unique! We continue along Route 66, enjoying the ride (undoubtedly the most beautiful part of this itinerary) until we arrive in Amarillo , a lively Texan town where we stop for the night - and to eat! Have we tasted pulled pork yet? One thing is certain: in these parts we will not be hungry.

We get up early and have a nice breakfast (one of the best things in the States!) with bacon and eggs and then, before setting off, we stop at the Cadillac Ranch , a monumental sculpture on display outdoors - a series of scrapped Cadillacs that seem to sprout from the ground, a tribute to Bruce Springsteen's album “The River”. Let's take some pictures and then it is time to say goodbye to Texas. We continue our journey along Route 66 continues west and end up in New Mexico! We make a stop at the Blue Swallow Motel , one of the symbols of Route 66, and then head to Santa Rosa for lunch, which we do in one of the various Route 66 themed diners.

In the afternoon we head towards the heart of New Mexico and reach Santa Fe , which holds lots of charm! Here, we park the cars and stretch our legs, taking a stroll in the centre, the Old Town, with the Cathedral Basilica of San Francesco d'Assisi and Santa Fe Plaza, the heart of Santa Fe. Here, we take a break from the hamburgers and fries and treat ourselves to a typical Mexican dinner in a traditional restaurant - if not here, where?!

We have now reached the middle of the journey and we can safely admit it… all these kilometers are starting to take a toll! Because of this, we have decided to not change accommodation for tonight so we can all chill out a bit. We will spend all day in Santa Fe, so we can relax a bit, do some laundry (yes, we know you need it!) and enjoy the city properly.

Ready to step into a movie? Actually no, sorry... a TV series! We set off early in the morning and reach Albuquerque, which has become quite famous after the very famous series  "Breaking Bad"  - where it is set - and therefore if we feel a bit in the mood of the show, don't worry. The important thing is that none of us rent an RV and start producing meth in the desert. Clear?

We visit the Old Town, which reminds us of Santa Fe, and then we can go to the  Rattlesnake Museum , a museum dedicated to the rattlesnake, one of the symbols of this area of ​​the United States. Then we move to West Park , a vast park that sits on the banks of the Rio Grande River, where we can lie in the sun and enjoy some peace and quiet.

After visiting Albuquerque we will arrive in Gallup, a town close to the New Mexico border, where we stop to explore the surroundings. We can take a walk to Red Rock Park , where we can finally see the rock formations with the typical reddish colour of this area up close. We spend the evening and the night in Gallup, immersed in the desert.

Bye bye New Mexico, it's time to cross the Arizona border ! Can you feel the Pacific Ocean breeze from here? Metaphorically speaking, of course: we are in the middle of the desert! We certainly notice it in the Painted Desert , located in the eastern end of the Grand Canyon Park , which is today's first stop: ready to be amazed? This desert is composed of stratified faults that date back to the Triassic - erosion has since made all these layers visible, which make the rocks multicoloured.

After the painted desert, the petrified forest awaits us! The Petrified Forest National Park has the unique feature of containing an incredible amount of fossilised tree trunks, which date back more than 200 million years. A real open-air museum that will leave us breathless - we explore the park and then, very hungry, we reach Holbrook , where we stop to eat at the famous Joe and Aggie's Cafè (a must on Route 66) and to spend the night.

Arizona is giving us the most unique landscapes: even this morning it won't leave us dry as we push towards Sedona. But we certainly don't stop in the city, we continue towards… a meteorite crater! We are in the middle of the desert , where, about 50,000 years ago, a meteorite crashed and in doing so has left its mark up to the present day: with a diameter of about 1,200 meters and a depth of 170, it is an incredible natural spectacle. Shall we bring breakfast all the way here? Because how many of us will ever be able to say that they drank coffee sitting on a crater created by a meteorite?

The surprises don't end here: we continue in the Sedona area until we reach the Red Rock Crossing , where an easy trek awaits us that takes us in the presence of rock formations with an intense red colour, called Cathedral Rock , given their resemblance to imposing cathedrals. The show is guaranteed - especially if we stay until sunset. But let us remember that more than 3 hours await us on the road : tonight we have to get to Kingman , now on the border with California . Are we ready to enter the Golden State?

Ready for another day of adventures? Today we head towards Flagstaff , a very busy town on Route 66 because it is on the road to what everyone considers to be the most famous park in the United States… the Grand Canyon ! We don't expect much from Flagstaff except the historic centre that has the old western vibe we've become accustomed to in recent days. But let's not stop for too long here, because today's real protagonist is another... we're obviously talking about the Grand Canyon. Sure, it's not on Route 66, so that would be out of the ordinary - but we've come this far, what's another hour and a half drive to admire this natural wonder?

The Grand Canyon cannot be described - it can only be experienced. To give you an idea: before your eyes appears this gigantic rocky fault that seems to have no end, and which extends as far as the eye can reach, with its thousand shades of red, ocher and brown. A unique show that we couldn't miss: we enjoy it to the fullest, perhaps walking along some paths to go further down, towards the canyon, and then staying until sunset, the most incredible time to be here. We then return to Flagstaff to spend the evening.

This morning, guess what? We're back on the road, and our destination is the legendary Las Vegas!

Today is all about relaxation, as we'll be staying here tonight and won't be driving again until tomorrow. We’ll explore the most amazing hotels in the city, from Venice (The Venetian) to New York (Hotel New York-New York). Maybe we’ll hit a pool party or try our luck at a casino—be careful with your wallet though, always gamble responsibly! As night falls, everything lights up, offering us an unforgettable show, especially the Bellagio Fountains. There’s a reason why so many hotels are inspired by Italian cities!

You can't be in Sin City without experiencing a wild night: we’ll get all dressed up, maybe splurge on renting a limousine (quite common around here!), and decide which of the many clubs we’ll party at!

It's been 12 days since we left Chicago, crossing three-quarters of the U.S., and today is the last road trip of our journey—so let's make the most of it. Leaving behind the bright streets and luxurious hotels, we head to Los Angeles. We arrive around lunchtime, finding comfort in milkshakes, burgers, and fries at a diner.

Finally, relax

We spend the afternoon at Santa Monica Pier, the end of Route 66, and take the iconic photo by the sign. From Lake Michigan to the Pacific Ocean, this incredible journey is an unforgettable, once-in-a-lifetime experience. Let's savor it! We walk the pier, perhaps daring to ride the roller coasters, and then wait for the sunset on the beach, sipping drinks at Venice Beach.

We conclude the day, and our trip, with one final dinner together. It will be sad to say goodbye after all we've experienced, but we'll toast to us and to Route 66!

Time to ditch our rental cars and say goodbye; our trip to the States ends here: see you soon for another WeRoad.