Route 66 – Where to BEGIN a Road Trip? CHICAGO or LOS ANGELES?

Route 66 – Where to BEGIN a Road Trip? CHICAGO or LOS ANGELES?

You may be wondering: “Where to BEGIN Route 66 Road Trip? CHICAGO or LOS ANGELES?”, “Where to start route 66 trip?”, “Where is the best place to start Route 66?” Deciding where to start your Route 66 journey can be a difficult decision, as both Chicago and Los Angeles offer unique benefits and drawbacks. In this blog post, I will explore the pros and cons of starting your Route 66 trip in both Chicago and Los Angeles, to help you make an informed decision and plan your ultimate road trip adventure.

Route 66 is one of the most iconic road trips in the United States, stretching over 2,400 miles from Chicago, Illinois to Santa Monica, California. Both starting points have their own unique charm and attractions, so the decision of where to begin your journey is a matter of personal preference.

Starting Route 66 in Chicago:

Where to BEGIN Route 66 Road Trip? You can choose Chicago or Los Angeles/ Santa Monica.

Chicago, known as the “Windy City,” is a vibrant city that boasts a rich history, stunning architecture, and world-class cultural attractions. As the starting point of Route 66, it offers a unique opportunity to immerse yourself in the history of the road before embarking on your journey.

One of the must-see attractions in Chicago is the Art Institute of Chicago, which houses one of the largest collections of Impressionist and Post-Impressionist paintings in the world. Another must-visit attraction is the Willis Tower, formerly known as the Sears Tower, which offers breathtaking views of the city from its Skydeck.

Where is the best place to start Route 66? Maybe Chicago?

Starting your road trip from Chicago also allows you to explore the Midwestern United States, including states like Illinois, Missouri, Oklahoma, and Texas, which offer a mix of urban and rural landscapes, as well as cultural and historical attractions.

However, starting in Chicago also means that you’ll face more challenging weather conditions, as the city is known for its harsh winters. Additionally, traffic can be congested in the city, making it more difficult to get out of town and onto the open road.

👍 PROS of starting Route 66 in Chicago:

Where to start Route 66 trip? Chicago could be a great starting point for your journey.
  1. Rich history: Chicago is the starting point of Route 66 and is steeped in the history of the road and the American highway system.
  2. Cultural attractions: Chicago is a culturally rich city with world-class museums, theaters, and art institutions, including the Art Institute of Chicago and the Willis Tower.
  3. Exploring the Midwest: Starting in Chicago allows you to explore the Midwestern United States, including states like Illinois, Missouri, Oklahoma, and Texas, which offer a mix of urban and rural landscapes, as well as cultural and historical attractions.
  4. Convenient transportation: Chicago is a major transportation hub, with two airports and easy access to rental cars, making it convenient for those who want to start their road trip from there.

👎 CONS of starting Route 66 in Chicago:

Pros and cons of starting Route 66 in Chicago.
  1. Harsh weather: Chicago is known for its harsh winters, which can make for a less enjoyable road trip experience during the colder months.
  2. Congested traffic: Traffic can be congested in the city, making it more difficult to get out of town and onto the open road.
  3. Cost: Starting in Chicago may be more expensive due to higher prices for accommodations, food, and attractions in the city.

What travel guide do I need if I travel westbound along Route 66?

What travel guide do I need if I travel westbound along Route 66? Which route is better? westbound or eastbound?

Traveling westbound along Route 66 is a classic American road trip experience, taking you from Chicago to Santa Monica along one of the most iconic highways in the United States. Westbound travel offers a journey through the heart of the country, from the bustling cities of the Midwest to the scenic deserts of the Southwest, and the stunning Pacific coastline. Whether you are a history buff, a nature lover, or simply looking for a classic American adventure, traveling westbound along Route 66 is sure to be a trip of a lifetime.

Route 66 - travel guide westbound. Where to start your Route 66 journey?

I can recommend the special westbound edition of the travel guide “Route 66 – 202 Amazing Places” by Mark Watson for your Route 66 journey. This comprehensive guide is tailored for travelers who are embarking on a westbound adventure along the historic highway, offering a wealth of information on the must-visit sights and unique experiences along the way. From the bustling cities of Illinois to the stunning coastline of California, this guide is a valuable resource for anyone looking to make the most of their Route 66 journey.

Read more about the best stops in Illinois in my blog post: Route 66 in Illinois – The TOP 5 BEST Stops – What to Visit/See Along Mother Road in IL?

Starting Route 66 in Los Angeles/Santa Monica:

Starting Route 66 journey in Los Angeles/Santa Monica.

Los Angeles, the city of angels, is a hub of creativity, innovation, and entertainment. It is home to many famous attractions such as the Walk of Fame, the Hollywood Sign, and the Sunset Strip.

Starting your road trip from Los Angeles also gives you the opportunity to explore the Pacific Coast and some of the most beautiful scenic routes in the United States, including the Pacific Coast Highway and Big Sur. This route is particularly popular among those who enjoy breathtaking views of the ocean, mountains, and forests.

Santa Monica pier could be your finish or start. Get ready for your road trip along Route 66.

Additionally, starting in Los Angeles means that you’ll be able to enjoy mild weather year-round, making it easier to spend more time on the road and less time holed up in your car or hotel room.

However, starting in Los Angeles also means that you’ll face more traffic, particularly in the city and along the Pacific Coast Highway, which can make for a slower and more stressful journey.

👍 PROS of starting Route 66 in Los Angeles:

Where to start Route 66 journey?
  1. Mild weather: Los Angeles offers mild weather year-round, making it easier to spend more time on the road and less time holed up in your car or hotel room.
  2. Pacific Coast: Starting in Los Angeles gives you the opportunity to explore the Pacific Coast and some of the most beautiful scenic routes in the United States, including the Pacific Coast Highway and Big Sur.
  3. Entertainment: Los Angeles is a hub of entertainment, with famous attractions such as the Walk of Fame, the Hollywood Sign, and the Sunset Strip.
  4. Convenient transportation: Los Angeles has two major airports and easy access to rental cars, making it convenient for those who want to start their road trip from there.

👎 CONS of starting Route 66 in Los Angeles:

Pros and cons of starting Route 66 in Los Angeles/ Santa Monica.
  1. Heavy traffic: Los Angeles is known for its heavy traffic, particularly in the city and along the Pacific Coast Highway, which can make for a slower and more stressful journey.
  2. Cost: Starting in Los Angeles may be more expensive due to higher prices for accommodations, food, and attractions in the city.
  3. Urban landscape: Los Angeles is a large, densely populated city, so starting your road trip from there may not provide the rural, scenic experience that some travelers are seeking.

What travel guide do I need if I travel eastbound along Route 66?

What travel guide do I need if I travel eastbound along Route 66?

Traveling eastbound along Route 66 is a less common route compared to traveling westbound, but it offers its own unique set of experiences and attractions. Some travelers prefer to start their Route 66 journey in Santa Monica and work their way eastward to Chicago, taking in the beauty of the American Southwest and the Midwestern United States along the way. Regardless of which direction you choose to travel, a comprehensive travel guide and detailed plan can help ensure that you make the most of your Route 66 adventure.

Route 66 Travel Guide - 202 Amazing places by Mark Watson. - Santa Monica to Chicago Eastbound edition.

I recommend the special eastbound edition of the travel guide “Route 66 – 202 Amazing Places” by Mark Watson for your Route 66 journey. This comprehensive guide is designed specifically for those traveling eastbound along the historic highway and provides in-depth information on the must-see sights and hidden gems along the way. From the colorful deserts of Arizona to the charming small towns of Missouri, this guide is a must-have for anyone embarking on a Route 66 adventure.

Read more about the best stops in California in my blog post: Route 66 in California – The TOP 5 BEST Stops Places to visit Along Mother Road in CA – What to see?

Where is the best place to start Route 66?

Where is the best place to start Route 66?

In conclusion, both Chicago and Los Angeles have their own unique charm and attractions, and the decision of where to start your Route 66 road trip ultimately comes down to personal preference. Whether you prefer to start in the Windy City or the city of angels, Route 66 promises to be an unforgettable journey filled with stunning landscapes, fascinating history, and unforgettable experiences.

👍 Find out more:

Discover the best stops along the Mother Road in my travel guide, “Route 66 Travel Guide – 202 Amazing Places”, which is available on Amazon. This is the ultimate travel guide and pocket reference for anyone wishing to experience the nostalgia and wonder of America’s Route 66! MUST-HAVE for all Route 66 travelers. Visit 202 places on Route 66 with “Scan QR and go” for easy navigation.

Author:

Traveling on Route 66

Mark Watson is a California-based member of a Los Angeles Motorcycle Club and a keen traveler. He’s traveled the entirety of U. S. Route 66 seven times on his Harley-Davidson. He strives to interest others in the historic drive to keep the legendary Route 66 alive. He also traveled through the Alaska Highway. He is an author of bestseller books on Amazon: “Route 66 Travel Guide – 202 Amazing Places” and “Alaska Highway – 202 Best Stops”.

2 thoughts on “Route 66 – Where to BEGIN a Road Trip? CHICAGO or LOS ANGELES?

  1. Gordon Langston says:

    Motel Munger Moss has had a significant downturn. Terrible bed. People arguing in the parking lot. People attempting to sell drugs in the back of the property.
    Some permanent residents. Crappy TV/cable.

    Reply
    1. Mark Watson says:

      Hi! Thanks for taking the time to share your thoughts, Gordon. Your input is much appreciated!
      It’s unfortunate to hear about the negative experiences at Motel Munger Moss. Even though Motel Munger Moss may not be the most comfortable place to stay, it still holds a special place in the hearts of many as an iconic roadside attraction. In fact, some travelers might only make a quick stop there just to take a photo and capture its unique vintage charm. The neon lights that illuminate the motel at night create a nostalgic and retro ambiance that many people find attractive.

      It’s alarming to hear about the drug dealers near Motel Munger Moss, but unfortunately, this is beyond the control of the motel’s owners… Unfortunately, these types of individuals can be found in many places, and it’s important to take precautions and ensure safety when traveling. Nevertheless, I hope that you had a wonderful time during your travels along the historic Route 66! Once again, thank you for taking the time to share your thoughts – your feedback is greatly appreciated!

      Mark Watson

      Reply

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