Best U.S. Road Trips: From Chicago to California (LA) on Route 66

If you’re thinking of a Chicago to California road trip, the most iconic experience will be to travel on route 66. This is one of the best US road trips and perhaps the best road trip from Chicago.

It’s southern route goes through eight states with many must-see attractions along the way. Find out what you should know to begin planning your trip from Chicago to LA, below.  

CONTENTS – In this article, you’ll learn about some of the best stops on route 66, plus important highlights as you drive Chicago to Los Angeles on Route 66:

Get Your Kicks on Route 66 – How to Plan A Chicago to California Road Trip

Route 66 is perhaps one of the most famous roads in the USA. 

In 1926, it was the first highway to be established in the country. The “Mother Road,” as it is sometimes known, linked Chicago to Los Angeles. Along the way, it crosses through eight states:

  1. Illinois
  2. Missouri
  3. Kansas
  4. Oklahoma
  5. Texas
  6. New Mexico
  7. Arizona
  8. California 

These days, it isn’t possible to drive the original Route 66 in its entirety due to diversions and bypasses. In fact, technically, the US Highway 66 no longer exists. 

Bit by bit, it was decommissioned between 1964 and 1985 due to potholes, cracks, impassable sections, and traffic swells beyond it’s two lane capacity. 

The good news is, when you drive Chicago to Los Angeles, even though the famous highway signs have come down, you can still drive around 85% of route 66. Even better, the road is well-maintained, even though it’s not a major travel route.

The roads link east to west, right across the heartland of America. It passes through big cities and small towns. Taking a Chicago to California road trip by way of route 66 is a great way to experience the real USA, and see a plethora of interesting attractions as you go. 

So if you are itching for an adventure, fasten your seatbelt and read on. You’ll be driving just under 2,500 miles – and it will be the trip of a lifetime!

Before Your Route 66 Road Trip Begins

When planning your road trip from Chicago to California, you should work out which towns and cities you would like to stop at along Route 66. Consider how much time you want to spend in each so you have the time to explore the attractions and feel refreshed for the drive.

It’s a good idea to book hotels in advance so you have a definite place to sleep at night. That way, you’ll avoid wasting time looking for accommodations and won’t stress out wondering where you’ll sleep. Car camping is not as fun as it might sound.

You will also need to arrange transport. 2,500 miles might be a lot to put on your own car(5,000 if you’ll be making a return trip). Perhaps you will drive Route 66 in style and hire a Ford Mustang or Mercedes convertible. If you go with a national car rental brand, you can drop the car off at your destination, then fly home out of LAX.

Once you have booked accommodation at all your stopovers, and know what vehicle you’ll drive, it is time to begin your adventure in Chicago.

Related Article: Learn the basics of taking a road trip.

Taking Route from Chicago to Los Angeles

You’ll want to make multiple stops along the way when you’re taking route 66 from Chicago to Los Angeles. Here is what we recommend as the best route.

Route 66 Start: Chicago, the Windy City 

Chicago is known for its high-rise buildings, rich history, and jazz and blues music. When in this fantastic city you will need to go to some downtown bars and soak up the atmosphere.

Feast on world-famous Chicago hot dogs and deep dish pizza while watching the Chicago Bulls basketball team shoot some hoops.

Get your fill of this fantastic city before you pick up Route 66 in Chicago.

Related Article: Learn about these must see attractions and travel tips for Chicago.

Iconic Attractions Along the Way

From Chicago, you will drive west through Springfield, Illinois, where you can visit the Cosy Dog Drive In. Supposedly, this is where the first corn dog was invented. 

From there, you can drive to St Louis, Missouri. Stop to enjoy listening to some traditional blues music in bars located along the banks of the Mississippi River. 

Then take a tram ride up 630ft to the top of the iconic Gateway Arch

This spectacular monument was built in the 1960s to honor the frontiersmen who traveled west and discovered the Great Plains and beyond. 

Historic Stops, Like Jesse James’ Hiding Spot

A must-see is the Meramec Caverns in Missouri.  These are natural limestone caves that are collectively about 4.6 miles long. Not only have ancient artifacts been found here, but it is thought to be where outlaw Jesse James hid from law enforcement.

Drive on to visit Oklahoma City, Oklahoma. Here, you can find some of the original and iconic Route 66 hotels, motels, and gas stations

To further increase your historical knowledge of the “Mother Road” (as Route 66 is sometimes called) head over to Amarillo, Texas. This town hosts the Route 66 museum.

Next, you’ll want to spend a day or two in Santa Fe, the capital of New Mexico. It is the oldest capital city in the United States, founded on the ruins of an abandoned Indian village. Today, twenty-three Native American Tribes, Nations, and Pueblos reside in this fascinating city.

Scenic Attractions Way Out West

One of the most spectacular sights you will see on your journey across the middle of the US is the Grand Canyon. There is a lot you will want to do here, including:

  • Stretch your legs after driving so long.
  • Walk along the Rim Trail.
  • Climb to the top of a stone watchtower and marvel at the views that extend over 100 miles on clear days.

There’s No Place Like Las Vegas

After absorbing so much history along your journey, it’s time to let your hair down, and what better place to do this than Las Vegas

Traveling from Chicago to Las Vegas route 66 is an adventure, but so is Las Vegas itself! 

That’s why you may want to spend a few nights here. Be sure to take in the jaw-dropping sights from:

  • Neon lights
  • Casinos
  • World-class cabaret shows
  • Luxurious hotels

Take your time here, because it’s a one-of-a-kind experience, for sure.

The End of Your Chicago to California Road Trip: LA

Eventually, you will reach Los Angeles, where your journey will end – in style. So many LA sights will be familiar if you are a fan of movies. 

  • You can follow in the footsteps of pretty woman, Julia Roberts on Rodeo Drive
  • Roller skate alongside Santa Monica beach
  • Rake a selfie beside the iconic Hollywood sign

You might be surprised to know there are plenty of free things to do in LA.

Related Article: Take not of these Hidden Gems in Los Angeles

Final Thoughts on  Best U.S. Road Trips

Well, you have driven over 2,400 miles across eight states, you know some of the best things to see on Route 66, and now it’s time to go home. One thing is for sure; you will never forget the kicks you got on Route 66.

Want to try another of the Best US Road Trips? Your next drive could be a road trip on the Pacific Coast Highway!

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Jackie Gately

Jackie Gately is a seasoned travel writer, photographer, and marketing consultant who is passionate about travel. She loves casual-luxury experiences, coastal getaways, cultural attractions, and local, wholesome food and wine pairings. A perfect day ends with her toes in the sand or by chasing the sunset with her camera--ideally both.

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