Take Off On a Route 66 Ride from Chicago to Los Angeles

Jun 4, 2025

Route 66 has been part of American travel history since 1926, when it first connected Chicago to Los Angeles and opened the door to cross-country road trips unlike anything people had seen before. Over time, it became more than just a way to get from one place to another. It was a lifeline during the Dust Bowl, a path west for families chasing work and opportunity, and eventually, a symbol of freedom and exploration for travelers from around the world.

Even now, people come from every corner of the globe to follow the same stretch of highway, hoping to see the landmarks, roadside attractions, and old towns that helped make the route famous. Riding the Route 66 Chicago to Los Angeles stretch today gives you a chance to experience that history firsthand while also enjoying some of the country’s most unique and memorable places. In this blog, we’re walking through some of the most well-known and interesting stops to check out if you’re planning to ride the full route.

So, How Long Does it Take to Drive from Chicago to LA on Route 66?

The full drive from Chicago to Los Angeles on Route 66 covers just over 2,400 miles, and most riders take about two to three weeks to complete it. That timing allows for stops at major landmarks, time to explore small towns, and the chance to enjoy what makes the route so well-known. Some riders try to cover the distance in a week or less, but that often means being on the road for long hours every day without much time to take in the places that give Route 66 its charm.

How Much of Route 66 is Still Drivable?

Roughly 85% of the original Route 66 is still drivable today, though the exact number can vary depending on how much of the old road you’re aiming to follow. While the highway was officially decommissioned in 1985, large portions have been preserved or restored as Historic Route 66. Some parts have been rerouted or replaced by interstates, but in most cases, you can still follow the path closely with the help of maps, guidebooks, or GPS tools built specifically for the route.

1. Gemini Giant – Wilmington, IL

Approximate distance from Chicago: 62 miles

One of the first memorable stops after leaving Chicago is the Gemini Giant, a towering fiberglass statue that’s been catching travelers’ attention since the 1960s. Standing outside what used to be the Launching Pad Drive-In, the figure is part of a series of “Muffler Men” that were once used for advertising across the country. What makes the Gemini Giant stand out is his space-age helmet and rocket, a nod to the fascination with space travel during the Cold War era. It was named after NASA’s Gemini space program, and over the years, it’s become one of the most photographed landmarks on Route 66. For many riders, stopping here marks the real beginning of the road trip, with a mix of nostalgia and Americana that sets the tone for everything that follows.

2. Meramec Caverns – Stanton, MO

Approximate distance from Gemini Giant: 306 miles

After leaving Wilmington, the drive continues through Illinois and into Missouri, where one of the most well-known natural attractions on Route 66 comes into view. About 306 miles from the Gemini Giant, Meramec Caverns in Stanton has been drawing visitors underground since the 1930s. These limestone caves stretch for over four and a half miles and were once used as a hideout by the outlaw Jesse James, according to local legend. 

What really helped put Meramec Caverns on the map, though, was the advertising. Hundreds of barns across multiple states were painted with bright signs that read “See Meramec Caverns,” turning the site into a must-stop for families making the trip west. The tradition of roadside marketing became part of the route’s identity, and the caverns remain one of the most visited stops along the highway today.

3. Cars on the Route – Galena, KS

Approximate distance from Meramec Caverns: 240 miles

After crossing through Missouri, Route 66 dips briefly into Kansas, where it covers just 13 miles, but that short stretch still packs in some memorable stops. About 240 miles from Meramec Caverns, Cars on the Route in Galena is a restored Kan-O-Tex gas station that’s become a fan favorite, especially for anyone familiar with Pixar’s Cars. The old tow truck sitting outside served as the real-life inspiration for Tow Mater, one of the movie’s most recognizable characters. Inside, the small station has been turned into a Route 66-themed shop and snack stop, complete with local history and nods to the animated film. Galena may only have a small piece of the route, but it’s a great example of how even the shortest sections can have a lasting impact on travelers making their way across the country.

4. Blue Whale of Catoosa – Catoosa, OK

Approximate distance from Cars on the Route: 94 miles

Just under 100 miles past Galena, Route 66 takes you into Oklahoma, where you’ll find one of the most recognizable landmarks along the entire route. Sitting just off the highway in Catoosa, the Blue Whale was built in the early 1970s as a gift from a local man to his wife. What started as a personal project quickly turned into a popular swimming spot for families in the area, complete with slides, picnic tables, and a small zoo nearby. Over the years, it became a regular stop for roadtrippers looking for a place to stretch their legs and take a photo. The whale itself is nearly 80 feet long and has become something of a Route 66 mascot, especially in Oklahoma.

5. Cadillac Ranch – Amarillo, TX

Approximate distance from Blue Whale: 390 miles

After crossing through Oklahoma and heading into the Texas Panhandle, Route 66 leads you to one of the most photographed stops along the entire drive. About 390 miles from the Blue Whale, Cadillac Ranch sits just outside Amarillo and features ten vintage Cadillacs buried nose-first in the ground. The installation was created in 1974 by a group of artists known as the Ant Farm and has been drawing attention ever since. Unlike most roadside stops, this one invites visitors to take part by bringing spray paint and adding their own layers of graffiti to the cars. The colors and messages are always changing, so no two visits look the same.

6. Tucumcari Murals – Tucumcari, NM

Approximate distance from Cadillac Ranch: 109 miles

Roughly 109 miles west of Amarillo, the route brings you into Tucumcari, New Mexico, a town that’s kept its connection to Route 66 alive through both its architecture and its art. Tucumcari is well known for its vintage motels, including the Blue Swallow and Motel Safari, both of which have been welcoming travelers since the mid-1900s. What really stands out today, though, are the more than 40 hand-painted murals scattered throughout the town. These murals cover the sides of buildings and tell the story of Tucumcari’s past, from early railroad days to the rise of car travel through the Southwest. They give visitors a visual way to connect with the history here, offering something to see around just about every corner.

7. Petrified Forest National Park – Holbrook, AZ

Approximate distance from Tucumcari Murals: 380 miles

After leaving Tucumcari, the route carries you across the New Mexico border and into Arizona, where the landscape starts to shift and the history takes a different shape. About 380 miles from Tucumcari, Petrified Forest National Park near Holbrook offers a completely different kind of stop compared to the vintage motels and murals earlier in the trip. This is the only national park that includes an original stretch of Route 66, complete with old telephone poles still standing along the path. 

Visitors can walk through areas filled with fossilized logs that date back over 200 million years, giving a look into a prehistoric world that once covered this part of the Southwest. There are also petroglyphs, desert views, and park exhibits that explain the connection between the land and the highway that cuts through it. With Los Angeles still over 550 miles away, this stop offers a quiet, open space to explore before continuing toward the final leg of the trip.

8. Santa Monica Pier – Santa Monica, CA

Approximate distance from Los Angeles: 17 miles

By this point, you’ve reached your Los Angeles destination, but that’s not really where this experience ends. About 17 miles west of downtown LA, the Santa Monica Pier marks what many people consider the true finish line of Route 66. While it wasn’t part of the original 1926 alignment, the pier is home to the famous “End of the Trail” sign that has become one of the most recognized photo spots along the route. Travelers from around the world make their way here to stand beneath the sign, take in the ocean views, and reflect on everything they’ve seen along the way. With restaurants, small shops, and the sound of the Pacific in the background, it’s a fitting place to close out the trip.

Made it to California? Keep Exploring.

Finishing Route 66 at Santa Monica Pier doesn't have to mean the end of the ride. California has some of the best coastal and canyon roads in the country, and Riders Share offers guided motorcycle tours across the state led by locals who know the routes from Los Angeles up through Big Sur and beyond. If you've got time after the cross-country stretch and want to see more of the West Coast, a guided tour is a great way to keep the trip going without planning every mile yourself.

Extra Route 66 Attractions

We didn’t get a chance to mention a few of the following Route 66 locations, but they’re worth the stop if you’ve got some time along the way. 

• Route 66 Start Sign (Chicago, IL): The official starting point of Route 66 is located at Adams Street and Michigan Avenue. It’s a must-snap photo spot for anyone beginning their Route 66 road trip.
• Mural City (Pontiac, Illinois): Home to the Route 66 Hall of Fame and Museum, Pontiac features over two dozen colorful murals spread across its downtown buildings. It’s a great place to stop for photos and a deeper look at the route’s legacy.
• Chain of Rocks Bridge (St. Louis, MO): Built in 1929, this bridge once carried Route 66 across the Mississippi River. It’s known for its unusual 22-degree bend and is now open to pedestrians and cyclists.
• Round Barn (Arcadia, OK): Built in 1898, this perfectly round barn is a standout Route 66 attraction and a great place to learn a bit about Oklahoma farming history.
• The Big Texan Steak Ranch (Amarillo, TX): Known for its 72-ounce steak challenge, this old-school Texas restaurant has been a staple for Route 66 travelers since 1960.
• Standin’ on the Corner Park (Winslow, AZ): A tribute to the Eagles’ song Take It Easy, this park is a fun stop with a statue, mural, and commemorative signs for photo ops and musical nostalgia.

Ride Route 66 from Chicago to Los Angeles on a Motorcycle Rental from Riders Share

Planning to take on the full Route 66 ride? Start with a motorcycle rental in Chicago through Riders Share and experience the entire stretch from the Midwest to the Pacific. Our network offers a wide range of bikes so you can find something that matches the kind of ride you’re looking for. If you’re starting from the West Coast instead, you can just as easily pick up a motorcycle rental in Los Angeles and head east toward Chicago, taking in each stop along the way. However you plan your trip, Riders Share makes it easy to explore Route 66 on your terms.

Before You Go

Before you set off, it’s worth remembering that riding Route 66 from Chicago to Los Angeles is a major trip that covers over 2,400 miles and crosses eight states. Planning ahead can make all the difference, especially when it comes to pacing, weather, and keeping your bike in good shape throughout the ride. Bring what you need, know your route, and give yourself time to enjoy the places that make this road so memorable.