Chicago to California – A Scenic American Road Trip on Route 66

Plan a road trip from Chicago to California for the adventure of a lifetime on the legendary Route 66. Sure, it’s a long journey—but for anyone interested in classic Americana history, this 2,448- mile trek through the middle of the country is full of world-famous sites and iconic, “only in America,” attractions.

"Before you get your motor running and head out on the highway, you’ll need a plan—this 40+ hour drive has more incredible stops than you could possibly fit into a single trip."

While there are certainly faster and more convenient ways to travel from the Midwest to the West Coast, none are quite as fascinating as this leisurely Chicago to California drive past old trading posts, classic diners, sparkling neon signs and other memorable sights.

• The drive takes about 40 hours. Plan to be on the road for at least five days—or longer—depending on how many stops and side trips you make. Route 66 rolls through small towns (with plenty of stop lights) along the way, so you won’t be driving as fast as you would on an interstate highway.
• Be sure you have a good overview map. Few modern maps even show the historic highway anymore (it was first commissioned back in 1926), but several are available online. Once you're out on the open road, you'll see the route and its historical markers along the way.
• Make lodging reservations in advance. By today's standards, this is the road less-traveled—meaning there are fewer nearby hotels and more “no vacancy” signs. Book a Choice hotel in advance to be sure you have a place to stretch out and rest before heading back on the road.
• Think about what you want to see along the way. Some websites offer turn-by-turn Route 66 road trip planners, showing an abundance of attractions, restaurants, souvenir shops and must-see museums. Make a list of where you want to stop before you hit the road, but always leave a little time for an unexpected side trip or two.
• Consider the side trips. While there is plenty to see along Route 66, a detour is sure to delight your carload. Country-music boomtown Branson, MO, is just 50 miles south of Springfield. The Grand Canyon is about 90 minutes off the highway in northern Arizona, and the spectacular Hoover Dam is less than 100 miles northwest of Route 66 on the Arizona-Nevada Border—just to name a few.

Start your epic Route 66 road trip in the iconic Windy City. There’s so much to do and see in Chicago that you might get distracted. But since time is limited, set your sights on enjoying the open spaces and city views you’ll find in Millennium Park. Make your next stop in Springfield, IL—the Land of Lincoln and the Birthplace of Route 66. Here you can snap a photo of the former president’s 19 th century home, visit his 117-foot tomb, and see the beautiful Illinois State Capitol. Finish out the first leg of the journey in St. Louis, MO. Stand in awe of the 630-foot Gateway Arch, the tallest monument in the Western Hemisphere, built to celebrate the westward expansion of the U.S.

You’ll want to start early, because the next stretch of highway will be your longest stint on the road. From St. Louis, you’ll travel southwest before hitting Sullivan, where an underground adventure awaits just outside town. Visit the Meramec Caverns, a series of caves where outlaw Jesse James once hid out with his gang. Just be sure to bring a jacket – the caverns are a chilly 58 degrees. Your next stop is in Claremore, OK, and the Will Rogers Memorial Museum. Stretch your legs in the serene countryside where the cowboy, comedian, commentator and “Oklahoma’s Favorite Son” called home before hopping back in your car to visit the Texas panhandle. While the song “Amarillo by Morning” might be playing in your head, you’re more likely to be here by sundown (depending on whether you decide to do this leg in one sitting). If you have time, make sure to stop by Cadillac Ranch, created in 1974 by a San Francisco art group. Bring a can of spray paint to add your own work to these 10 half-buried Caddies—or just snap a photo to add to your Route 66 vacation collage.

As you head further west, the states get bigger and the wide-open spaces seem like they stretch on forever. This third leg of your journey will take you through an area of the country that feels like it’s still part of the Old West. But once you hit Albuquerque, you’ll discover a quirky big city with plenty to see and do. Here, you can drive through a slice of classic Route 66 Americana with a cruise down Central Avenue—18 miles of vintage neon signs, motels and diners. Back on the road, you’ll find plenty of Route 66 inspired stops (and even a few ghost towns) in Arizona. You’ll want to take a short detour to Meteor Crater & Barringer Space Museum just 18 miles outside Winslow, AZ. A football-sized asteroid crashed here some 50,000 years ago and left a crater nearly a mile wide for you to explore. Finally, end your day in the town where The Eagles recorded “Take it Easy” in 1977; and be sure to get a pic of you “standin’ on the corner in Winslow, Arizona” while you’re here.

The final stretch of your Route 66 journey takes you from the high deserts of Arizona into sunny southern California. Your first stop is at the London Bridge (yes, that London Bridge) in Lake Havasu, AZ. Once spanning the River Thames in London from the 1830s through the 1960s, the bridge was sold for $2.4 million, disassembled, and then reassembled in Lake Havasu, of all places—and now offers the perfect photo-op. Next, cross the boarder into the Golden State and plan a visit to the famous Calico Ghost Town in Yermo, CA, near the Mohave Desert. This Old West mining town from the late 1800s once produced more than $20 million in silver over a 12-year span. Now, it offers ghost tours along Main Street, a self-guided tour into the depths of Maggie Mine, and a railroad tour around town. Finally, you’ll end this incredible journey where the road meets the sea in Santa Monica. Go for a swim or a jog at Santa Monica Beach, which has recently reopened for recreational use.