AAA Travel Tips / Chicago to Oklahoma City: 8-Day Road Trip Inspired by AAA Route 66 Road Fest

Chicago to Oklahoma City: 8-Day Road Trip Inspired by AAA Route 66 Road Fest
By AAA Travel Editors
March 14, 2023
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. If you decide to book the whole AAA Route 66 Road Fest experience, you’ll travel in style in a full-size motor coach, taking in the sights, sounds and experiences of one of the most popular, historic and iconic roadways in the country.
Though the official Route 66 Road Fest starts June 23-25, 2023, this itinerary and the 9-day Route 66 adventure are ones you can add to your bucket list or inspiration board as future road trip destinations; Route 66 has been welcoming travelers for 100 years. If you’re inspired to travel now, however, phone your local AAA Travel Agent for travel package reservations or email

Day 1: Start of Route 66 in Chicago

Welcome to the Windy City! There is no better place to start your Route 66 experience than at the Historic Route 66 sign in Chicago. Plan the perfect photograph at Grant Park on Adams Street in front of The Art Institute of Chicago. If you’ve purchased the vacation package, however, you’ll meet up with your local tour director on the first day, then join the group for a welcome dinner, followed by free time to see Chicago on your own.
Recommended accommodations: Palmer House - A Hilton Hotel.
AAA/Inspector 40

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 . 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.
Recommended accommodations: Drury Inn & Suites-St. Louis Southwest.

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 you’ve purchased the vacation package, you’ll dine in a restored 1930s art deco service station — Simple Pleasures, which is filled with cars and memorabilia. With the vacation package, your breakfast today is also included.
Recommended accommodations: Hilton Garden Inn Bentonville.
Crystal Bridges Museum of American Art

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. With the vacation package, your breakfast and lunch today will be included.
AAA/Inspector 15

Day 5: Oil Barons and Will Rogers

In the morning, depart Tulsa and travel to the incredible Woolaroc Ranch and Animal Preserve. Then, on to Bartlesville for a tour of the Phillips Petroleum Company Museum. Next, head to Claremore and the Will Rogers Memorial Museum, and visit Will’s Birthplace Ranch. For those on the official tour, there’s a fun, private dinner served in the barn and a chance to see the grounds before returning to Tulsa for overnight. Breakfast is also included today for those traveling with the group.
Wikimedia Commons / CC BY/MARELBU

Day 6: Route 66 in OKC

Enjoy a journey along historic Route 66 on your way 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. Afterward, if you’re arriving in Oklahoma City for the AAA Route 66 Road Fest, expect time to enjoy and explore on your own before returning to your Bricktown hotel. Breakfast will be included today as part of the vacation package.
Recommended accommodations: Hilton Garden Inn Oklahoma City-Bricktown.

Day 7: AAA Route 66 Road Fest

If you’ve arrived in Oklahoma City on June 19, 2022, plan to celebrate the AAA Route 66 Road Fest. For reserved guests, a shuttle bus will provide service between the hotel and festival throughout the day, and breakfast is included. If you're traveling independently, check out other road trips in the South Central Region or Oklahoma's Music Trail.
Recommended accommodations: Hilton Garden Inn Oklahoma City-Bricktown.

Day 8: Journey Home

Transfer to the Oklahoma City Airport for your departure flight home, or, if you booked the full Route 66 experience, travel on to Santa Monica and the end of the trail. Breakfast is included today if you’ve booked the vacation package.

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 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 For printed maps, AAA TourBook guides and trip planning advice, contact your local AAA office. For questions about AAA Route 66 Road Fest travel packages, contact your local AAA Travel Agent or email .