DAY 1-2 || Rome - Chicago

11:15 Rome (FCO) – 15:00 Chicago O’Hare (ORD) | flight time: 10h45

Chicago O’Hare Airport -> Chicago City Center (L train)

We reach the city center from the airport by metro. The rechargeable card Ventra Metro can be purchased in the station at the airport.

Tip: The Ventra card costs $5 and it’s  transferable on your credit card if you register within 90 days from purchasing it on the website Ventra Chicago. Furthermore one card is usable for more people. The cost of a single race with Ventra card is $2.25.

What to see in Chicago

SkyDeck $19.50
The Bean in Grant Park
Observe at the skyline from the Planetarium
Walk past the Chicago Theatre in the Loop
View skyscrapers and bridges from Bataan-Corregidor Memorial Bridge
Try the famous fried pizza

Stay overnight in Oak Park – Chicago, IL // Private Studio Coachhouse

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Sky Deck, Chicago

DAY 3 - Chicago, IL

If you’re going to be in Chicago the last weekend of July, get a ticket for the Lollapalooza festival!

Stay overnight in Oak Park – Chicago, IL // Private Studio Coachhouse

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Lollapalooza, Grant Park - Chicago

DAY 4 - Saint Louis, IL

Chicago, IL -> Saint Louis, IL | driving time: 4h10 – 465km

We rented the car through the site American Car Rental from O’Hare Airport for €800 + $750 to drop it off in Los Angeles + €11/day for total insurance (tyres, windscreen, theft, fire).

Tip: I generally recommend not to rent the GPS through the car company as it turns out to be quite expensive ($10-15/day). You should instead bring your own or even buy a new one (!). Or use GoogleMaps on your own phone with a local SIM card.

From the airport merge onto the Interstate 294 South and then move on to I55 WEST. This is already part of the Historic Route 66. From here on, you will need to enter and exit the Interstate in search of Route 66. Very often the Route 66 runs along the Interstate and, especially in the first half of the Route (I would say until the Oklahoma State) and I would suggest you take the Interstate to be able to go to a higher speed. The view and landscape is exactly the same! Obviously this is just a small personal advice since at the beginning we found a very repetitive landscape.

What to see

A statue of the Gemini Giant at the drive-in restaurant Launching Pad. This will be the first of many Muffler Man to chase around the United States. The next will be in Atlanta, always on the way to St. Louis. Here you will also find many buildings, shops and signage in American vintage style.

From here it begins the change of scenery and the roads stretching into the distance. You switch from the city sights to cornfields crops.

It is a good idea to stop at Midewin Tall Grass Prairie to admire the huge prairies.

From here on, you will see a lot of vintage gas pumps, cafe and motels scattered in small Route 66 villages.

The Arch Street graffiti, Atlanta.

St Louis’s Arch.

The Saint Louis Cardinals stadium, tickets from the matches from $5.

We stayed overnight in S. Louis, IL // Deluxe Motel – DO NOT STAY THERE – terrible!!

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Pompe di benzina, Illinois

DAY 5 - Springfield, MO

St. Louis, IL -> Springfield, MO | driving time: ~4h – 350km

Caveman Zipline at Meramec Caverns in Stanton, Missouri.

On the fifth day we waved the white flag to the millions fast food that have accompanied us throughout the journey so far and it was the best thing we could do (not only for our health but also for our joy)! In Springfield we found one of the best Vietnamese restaurants we’ve ever been to! It’s called Bambu and it’s 10 minutes away from the Rail Heaven motel. If, like us, you want to take a break from steaks and burgers, go to Bambu!

Stay overnight in Springfield, MO // Best Western Route 66 Rail Heaven

This is the motel where Elvis Presley stayed at! It’s beautiful, very well maintained motel with a vintage soul.  Definitely a must-see motel on the Route! It also has a swimming pool.

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Best Western Route 66 Rail Heaven

DAY 6 - Oklahoma City, OK

Springfield, MO -> Oklahoma City, OK | driving time: ~5h – 477km

What to see

A long detour and a few more wrong way more will get you to the Totem Pole Park in Foyil ..! In my opinion an enormous waste of time but if some fake totem fascinates you then this place is right up your street!

Oklahoma City Dodgers baseball match! Tickets from $8

Stay overnight in Oklahoma City, OK // Red Roof

DAY 7 - Tucumcari, NM

Oklahoma City, OK -> Tucumcari, NM | driving time: 5h30 – 600km

What to see

The Route 66 Museum in Clinton, OK. Admission $5

Cadillac Ranch – Amarillo, Texas. An art installation made of a row of Cadillac stuck in the ground.

Midpoint Cafe – Adrian, Texas.
The exact midpoint of the Route 66 between Chicago and Los Angeles!

Stay overnight in Tucumcari, NM // Blue Swallow Motel

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Route 66 Midpoint, Adrian TX

DAY 8 - Albuquerque, NM

Tucumcari, NM -> Albuquerque, NM | driving time: 2h30 – 280km

Tour of Albuquerque and rest of the day relaxing at the hotel pool.

Stay overnight in Albuquerque, NM // Best Western

DAY 9 - Holbrook, AZ

Albuquerque, NM -> Holbrook, AZ | driving time: 3h20 – 380km

What to see

Petrified Forest National Park

Painted desert

Indian Arts Center

Stay overnight in Holbrook, AZ // Wigwam Motel – Wonderful indian teepees

DAY 10 - Grand Canyon

Holbrook, AZ -> Grand Canyon, AZ | driving time: 2h30 – 260km

What to see

Breakfast near Standing ‘on the Corner Park, Winslow. Here there is also a huge crest of Route 66 – Arizona.

Meteor Crater. The “small” mark left by a meteorite that fell on the Earth 50 thousand years ago. Admission $18.

Twin Arrows, Arizona.

Here we leave Route 66 to visit the natural wonders of Arizona and Las Vegas. We will get back on the Route from Barstow, California.

Grand Canyon South Rim. Entrance fee $30, valid for 7 days.

For the more adventurous you can go down into the canyon, recommended the South Kalibab Trail.

For those who understand and speak English well you can get down and cross the canyon on the back of a mule! Here you can find more information.

Stay overnight in Valle, AZ // Grand Canyon Inn

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Standin’ on the Corner Park, Winslow
Twin Arrows, Arizona

DAY 11 - Monument Valley, Horseshoe Bend

Grand Canyon, AZ -> Monument Valley, UT | driving time: 2h20 – 245km

Another tour of Grand Canyon South Rim.

Monument Valley, entrance fee $20

Monument Valley, UT -> Page, AZ | driving time: 1h55 – 196km

Horseshoe Bend

Stay overnight in Page, AZ // Page Knight Inn Lake Powell

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Grand Canyon, Arizona
Horseshoe Bend, Arizona
Monument Valley, Utah

DAY 12 - Las Vegas

Page, AZ -> Las Vegas, NV | driving time: 4h10 – 440km

Before continuing the journey, you must visit the Antelope Canyon. It’s advisable to book in advance to visit the canyon in the best hours of the day (12-1 pm, when the sun is perpendicular and the colours are brighter), otherwise for any other slot time you can book the day before or the same day.

On the way to Las Vegas there is The Wave (Marble Canyon) in Coyote Buttes North. Only 20 people per day can visit this wonderful canyon and it is very difficult to get a permit. The permit is subject to a draw and can be requested starting from 4 months before the visit via this site.

In Las Vegas, go crazy!

Stay overnight in Las Vegas, NV // Flamingo LV Hotel & Casino

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Antelope Canyon, Arizona

DAY 13 - Las Vegas

Day at the pool.

Visit the hotels and casinos on Las Vegas Boulevard and get a photo of the “Welcome To Las Vegas” sign.

Stay overnight in Las Vegas, NV // Flamingo LV Hotel & Casino

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Las Vegas Boulevard, LV
One of the many casinos, Las Vegas

DAY 14 - Death Valley

Las Vegas, NV -> Barstow, CA via Death Valley | driving time: 5h10 – 511km

What to see

Visit downtown Las Vegas, the old town with the original strip and the old casinos

Death Valley

Rhyolite ghost town


Stay overnight in Barstow, CA // Route 66 Motel

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Badwater, Death Valley

DAY 15 - Los Angeles

Barstow, CA -> Los Angeles, CA | driving time: 1h50 – 185km

What to see

Santa Monica

Hollywood boulevard, Walk of Fame

Beverly Hills

Beverly Grove (murales Angel Wings di Colette Miller). For a full list of all the best graffiti in LA click here.

Stay overnight in Los Angeles, CA // Coral Sand Motel

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Santa Monica, end of Route 66

DAY 16 - Los Angeles

What to see

Griffith Observatory to view the city from the top

Hollywood sign

Universal Studios

Venice Beach

Stay overnight in Los Angeles, CA // Coral Sand Motel

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Hollywood, Los Angeles
Venice Beach, Los Angeles

DAY 17 - Long Beach

Los Angeles, CA -> Long Beach, CA | driving time: 30min

Car switch at LAX airport in Los Angeles.

Breakfast in Long Beach and sunbathing on the beach. (Beach at Long Beach not recommended)

Afternoon between Naples canals.

Stay overnight in Long Beach, CA // Hotel Current Long Beach

DAY 18 - Skydive

En route to Oceanside to skydive with an ocean view!

Afternoon spent at the hotel pool.

An alternative could be to stretch further south to San Diego stopping at Salvation Mountain.

Stay overnight in Long Beach, CA // Hotel Current Long Beach

DAY 19 - Manhattan Beach

Full day at Manhattan Beach.

Drop off the car at the airport and flight back to Rome.

19:45 Los Angeles (LAX) – 21:55 Rome Fiumicino (FCO)

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Manhattan Beach, California