Hitch a ride with us from the heartland of Chicago to the modern frontier of Oklahoma City in celebration of America’s Mother Road, Route 66, also known as Will Rogers Highway and the Main Street of America. This strip of Americana has been welcoming travelers for 100 years. Whether you’re dreaming of a future road trip or ready to hit the pavement now, this 8-day Route 66 adventure is one to add to your bucket list or inspiration board. For those who prefer to travel independently, the Mother Road offers countless opportunities to connect with locals, head off the beaten path and create meaningful experiences that will stay with you long after the road-tripping ends.
If you’d rather leave the planning to someone else, consider booking a AAA Route 66 Road Fest experience. You’ll travel in style in a full-size motor coach, taking in the sights and sounds of one of the most popular, historic and iconic roadways in the country. And if you’re looking to extend your Route 66 journey, don’t miss a special 9-day Route 66 road trip from Oklahoma to California.
Where does Route 66 start and end exactly? The full journey should begin in Chicago, Illinois and conclude at the Santa Monica Beach and Pier in California. However, AAA makes it easy to plan and configure where to go; together, these AAA itineraries offer a complete celebration of the iconic highway, from its bustling start to its nostalgic finish at the Pacific Ocean. If you’re inspired to travel, phone your local AAA Travel Agent for information and travel package reservations or email TravelAAA@aaacorp.com.
Day 1: Start of Route 66 in Chicago
Welcome to the Windy City! There is no better place to start your Route 66 adventure than at the Historic Route 66 sign in Chicago. Capture the perfect photo at Grant Park on Adams Street, framed by the iconic backdrop of The Art Institute of Chicago. While you’re here, take a stroll along The Magnificent Mile or soak in the views of the Chicago River, weaving through the heart of the city. If you're meeting a tour director and joining a group, a welcoming dinner might be on your itinerary. Otherwise, make time to see Chicago at your own pace.
- Stay: Palmer House - A Hilton Hotel.
Day 2: Chicago to St. Louis
Enjoy a classic American diner experience for breakfast. Travel to Pontiac and visit the Route 66 Association Hall of Fame and Museum. Then, arrive in Springfield and visit the Abraham Lincoln Presidential Library and Museum. Later, cross the Mississippi and arrive in St. Louis, your home for the night. Tonight, take in the captivating views of this wonderful city, as you join a Skyline Dinner Riverboat Cruise. If you opt for the vacation package, your breakfast and dinner today will be included.
Day 3: St. Louis to Bentonville
Take a guided tour of the Meramec Caverns in Sullivan, Missouri. In the afternoon, travel across Missouri to Arkansas and arrive in Bentonville to check into your hotel. If time allows, reserve time to eat and visit Simple Pleasures, a beautifully restored art deco service station. Perfect for celebrations or group tours, this retro venue is full of vintage cars and memorabilia, offering an experience as delightful as the dining itself.
Day 4: Bentonville to Tulsa
After breakfast, enjoy touring Bentonville, the birthplace of Walmart Stores Inc. Visit the Museum of Native American History for touring and plan to eat lunch at Fred’s Hickory Inn. Afterward, visit the Crystal Bridges Museum of American Art. Searching for the best place to stay? Enter Oklahoma on your way to Tulsa for overnight accommodations. If you have some free time, browse the Mother Road Market and eat, sip and shop.
Day 5: Oil Barons and Will Rogers
Leave Tulsa in the morning and make your way to the Woolaroc Museum & Wildlife Preserve, established in 1925 by Phillips Petroleum Company founder Frank Phillips, who wanted this working ranch to preserve the West as he knew it before the 20th century. After taking in the breathtaking scenery and fascinating history, continue to Bartlesville for a tour of the Phillips Petroleum Company Museum. From there, make your way to Claremore to explore the Will Rogers Memorial Museum (dedicated to the famed entertainer and member of the Cherokee Nation), and later finish your day with a visit to Will’s Birthplace Ranch. If you have a private dinner reservation, then you’ll enjoy a fun meal in the barn and get a chance to explore the grounds before heading back to Tulsa for the night.
Day 6: Route 66 to Chandler and OKC
Enjoy a journey along historic Route 66 to Chandler for a tour of the Route 66 Interpretive Center. Then, continue to Pops, an iconic stop along the old highway, for lunch on your own. Once you’ve soaked in the charm of the Mother Road, arrive in Oklahoma City for time to enjoy and explore on your own before returning to your Bricktown hotel. Stroll through the vibrant Bricktown neighborhood, where you’ll find places to eat ranging from quick eats to fine-dining restaurants. Take in the serene waterfront views along the canal or browse local shops for the perfect souvenir.
Day 7: OKC's Route 66
Oklahoma City earns its title as the Crossroads of America by sitting at the junction of key highways that link the country’s regions, making it a natural meeting place for travelers. As a gateway to the famed Route 66, it offers access to historic landmarks and other things to see. Celebrate the Mother Road by attending car shows or other nostalgic events hosted by groups like Route 66 Cruisers. Beyond the highway, explore vibrant neighborhoods like Bricktown, where canals, restaurants and shops bring the city’s character to life. Wrap up your day by unwinding at your Bricktown hotel and enjoying the stories of this historic destination.
Day 8: Journey Home
Before heading out, start your day with a hearty breakfast at one of Oklahoma City’s beloved local diners. Then, transfer to the Oklahoma City Airport for your departure flight home. If you intend to enjoy the full Route 66 experience, your journey will continue westward to Santa Monica, the iconic end of the trail. For independent travelers, consider extending your adventure with other road trips in the South Central Region or Oklahoma's Music Trail for even more unique experiences.
- Stay: Hilton Garden Inn Oklahoma City-Bricktown in Oklahoma, City, Oklahoma, or California's The Pierside Santa Monica.
Start Your Next Route 66 Road Trip with AAA
AAA Travel provides peace of mind for travelers — from the first mile of the journey to the last. Get inspiration for your next road trip and locate AAA Diamond-designated hotels and restaurants with AAA’s TripTik Travel Planner, or browse pre-planned itineraries on AAA.com/RoadTrips. Estimating fuel costs for your trip is easy with the AAA Gas Cost Calculator, and if your car needs a quick tune-up before the trip, find a AAA Approved auto repair facility near you at AAA.com/AutoRepair. For trip planning advice and questions about AAA Route 66 Road Fest travel packages, contact a AAA Travel Agent at your local AAA office.