
“Just so you know, some of the links on this page are affiliate links. This means that at no extra cost to you, I may earn a small commission if you make a purchase through these links. I only recommend products and services I genuinely believe in. Thanks for supporting the blog!”
From Chicago to Santa Monica: A Journey Along Historic Route 66!
One of the most iconic American road trips, Route 66 is the ultimate adventure for those looking to explore the heart and soul of the United States. From Chicago to Santa Monica, this legendary route offers an unforgettable mix of history, quirky roadside attractions, scenic landscapes, and nostalgic Americana. Before we dive into the 10 must-visit stops along the Mother Road, let me tell you why GetRentACar.com is the best place to book your cross-country ride.
Why GetRentACar.com?
When it comes to renting a vehicle for your Route 66 road trip, GetRentACar.com is the ultimate choice for a seamless and affordable experience. The platform offers a wide range of vehicles to suit your needs, whether you’re after a classic convertible for cruising the open road or an SUV for extra comfort. With competitive prices and excellent customer service, GetRentACar.com makes it easy to find a rental that fits your budget. Plus, with Trustpilot reviews highlighting their reliability and top-notch service, you can book with confidence knowing you’re in good hands. Whether you’re picking up your car in Chicago or Santa Monica, GetRentACar.com ensures a smooth rental process so you can focus on enjoying the adventure of a lifetime!

1. Chicago, Illinois: The Starting Point
Your Route 66 adventure begins in the bustling city of Chicago, home to the starting point of this historic route. Known for its towering skyscrapers, deep-dish pizza, and rich culture, Chicago has a lot to offer beyond just Route 66.
Must-See Attractions:
- Willis Tower Skydeck: Get a bird’s-eye view of the city.
- The Art Institute of Chicago: A world-class museum with art from various periods and cultures.
- Route 66 Begin Sign: Located at Adams and Michigan Avenue, it marks the official start of the journey.
Where to Stay:
- The Palmer House Hilton
Price: $$
Customer Rating: 4.5/5
Why: A historic, luxury hotel in the heart of downtown, with a rich history dating back to 1871. Perfect for starting your journey in style.

2. Pontiac, Illinois: A Roadside Museum
Just a couple of hours south of Chicago, Pontiac is home to a quirky collection of museums and Route 66 landmarks. This small town embraces its Route 66 heritage with flair.
Must-See Attractions:
- Route 66 Association of Illinois Hall of Fame & Museum: Learn about the road’s history with unique artifacts and exhibits.
- The Pontiac Oakland Auto Museum: A tribute to classic cars with a focus on Pontiac vehicles.
Where to Stay:
- Super 8 by Wyndham Pontiac
Price: $
Customer Rating: 4/5
Why: Affordable, clean, and located conveniently along Route 66 for a comfortable stopover.

3. Bloomington-Normal, Illinois: A Classic College Town
Next, head to Bloomington-Normal, a charming college town with a mix of history and contemporary fun.
Must-See Attractions:
- David Davis Mansion: A beautiful Victorian home, once owned by a U.S. Supreme Court justice.
- The McLean County Museum of History: Dive into the local history and culture of the area.
Where to Stay:
- DoubleTree by Hilton Bloomington
Price: $$
Customer Rating: 4.5/5
Why: Located near downtown, this hotel offers comfort and convenience with an exceptional customer service experience.

4. St. Louis, Missouri: Gateway to the West
St. Louis is a bustling city with rich history, and it’s a perfect midway point on your Route 66 journey. Famous for its Gateway Arch, this city serves as a reminder of America’s westward expansion.
Must-See Attractions:
- Gateway Arch: The iconic symbol of the city and the United States’ expansion westward.
- Old Courthouse: Historic site where Dred Scott sued for his freedom.
- Route 66 Car Museum: A collection of classic cars dedicated to the road’s history.
Where to Stay:
- The Chase Park Plaza Royal Sonesta St. Louis
Price: $$$
Customer Rating: 4.5/5
Why: A luxurious, historic hotel with exceptional service and located near the city’s top attractions.

5. Cuba, Missouri: A Hidden Gem of Murals
Cuba, Missouri, is a small town known for its colorful Route 66 murals that tell the story of America’s history and the road itself.
Must-See Attractions:
- The Mural City: Walk the streets and enjoy over 10 murals depicting scenes from Route 66’s history.
- Fanning 66 Outpost: Visit the world’s largest rocking chair and grab some classic Route 66 souvenirs.
Where to Stay:
- Econo Lodge
Price: $
Customer Rating: 4/5
Why: Simple, affordable, and conveniently located along Route 66, perfect for a quick rest before heading to the next stop.

6. Springfield, Missouri: Birthplace of Route 66
Springfield, Missouri, claims to be the birthplace of Route 66, making it an essential stop on your road trip. This city is rich in history and offers plenty to explore.
Must-See Attractions:
- Route 66 Car Museum: Featuring over 60 classic cars, this museum is a must for car enthusiasts.
- Bass Pro Shops Outdoor World: A massive retail complex with aquariums, nature exhibits, and outdoor gear.
- Mother’s Brewing Co.: A great spot to try some local craft beers.
Where to Stay:
- University Plaza Hotel
Price: $$
Customer Rating: 4/5
Why: Comfortable, conveniently located, and offers a nice mix of amenities for your stay.

7. Tulsa, Oklahoma: Art Deco and Music History
Tulsa is the heart of Oklahoma’s Route 66, with its stunning Art Deco architecture and vibrant music scene.
Must-See Attractions:
- Route 66 Historical Village: A collection of restored buildings, including a gas station, a diner, and more, celebrating Route 66.
- The Golden Driller: A giant oil worker statue that has become a Tulsa icon.
- Cains Ballroom: A legendary venue where many famous musicians performed.
Where to Stay:
- The Mayo Hotel
Price: $$$
Customer Rating: 4.5/5
Why: A luxury hotel with historical charm and excellent amenities in the heart of downtown Tulsa.

8. Amarillo, Texas: The Cadillac Ranch
Amarillo is known for its quirky attractions and its place in Route 66 lore.
Must-See Attractions:
- Cadillac Ranch: A public art installation where you can spray-paint classic Cadillacs buried nose-down in the ground.
- The Big Texan Steak Ranch: Home to the famous 72-ounce steak challenge.
- Route 66 Historic District: Explore the retro vibe of Amarillo’s Route 66 heritage.
Where to Stay:
- Courtyard by Marriott Amarillo West/Medical Center
Price: $$
Customer Rating: 4.5/5
Why: This is a stylish and comfortable option for travelers looking for a bit of luxury. The Courtyard offers a cozy atmosphere, a full-service restaurant, a heated indoor pool, and easy access to nearby attractions. It’s ideal for both business and leisure stays, with top-notch facilities.

9. Albuquerque, New Mexico: A Southwest Icon
Albuquerque is where Route 66 meets the Southwest, with stunning desert landscapes and a rich Native American and Spanish heritage.
Must-See Attractions:
- Old Town Albuquerque: Explore charming shops, galleries, and historic adobe buildings.
- The Albuquerque International Balloon Fiesta (if you’re there in the fall): A world-renowned event featuring hot air balloons.
- Route 66 Diner: A retro diner serving up classic American comfort food.
Where to Stay:
- Hotel Albuquerque at Old Town
Price: $$
Customer Rating: 4.5/5
Why: A beautifully restored hotel with great amenities and located close to Albuquerque’s Old Town.

10. Santa Monica, California: The End of the Road
Finally, after days of travel, you’ll reach the Pacific Coast and the iconic pier in Santa Monica. This marks the end of Route 66, where the road meets the ocean.
Must-See Attractions:
- Santa Monica Pier: An iconic landmark with an amusement park, aquarium, and family-friendly restaurants.
- Third Street Promenade: A lively shopping and dining area, perfect for your last stop on the journey.
Where to Stay:
- Shore Hotel
Price: $$$
Customer Rating: 4.5/5
Why: A sleek and modern hotel with ocean views, located just steps away from the pier, offering a great ending to your journey.
Conclusion
A Route 66 road trip is more than just a drive—it’s a journey through history, culture, and some of the most interesting parts of the United States. Whether you’re a history buff, a car enthusiast, or simply someone who loves a good road trip, there’s something for everyone along this iconic route. Don’t forget to book your vehicle with GetRentACar.com for the best deals and flexibility, and start your adventure today!
