Welcome to Chicago, the "Windy City," perched on the shores of Lake Michigan. Famed for its stunning architecture, vibrant arts scene, and cultural landmarks, Chicago offers something for everyone. Upon arrival, make your way to your hotel and dive right into the city's iconic attractions. Start with a visit to Millennium Park to marvel at the reflective Cloud Gate sculpture, affectionately known as "The Bean." Then, experience breathtaking views from the Skydeck on the 103rd floor of Willis Tower or enjoy a ride on the Centennial Wheel at Navy Pier. Chicago's world-renowned museums—such as The Field Museum, Shedd Aquarium, and the Art Institute of Chicago—are must-see destinations. By night, explore the city’s live music scene, whether it's the Chicago Blues Festival or intimate performances at legendary clubs like Buddy Guy's Legends. Chicago offers over 200 live music venues, ensuring something for every taste. Don’t forget to indulge in a deep-dish pizza at Gino’s East or Lou Malnati’s and sample the city's famous hot dogs. Round out the day by discovering Chicago’s craft brewery scene with a tour and a pint at a local favourite like Half Acre.

This morning, pick up your rental car and head out on the legendary Route 66, the historic highway that stretches from Chicago to Los Angeles. Illinois' portion of this iconic road is rich with Americana, dotted with nostalgic diners, quirky shops, and one-of-a-kind roadside attractions. Be sure to snap photos at the towering Rail-splitter Covered Wagon in Lincoln and the giant pink elephant at the Pink Elephant Antique Mall in Livingston. Stop in Pontiac to explore the Route 66 Association of Illinois Hall of Fame and Museum. Then, drive two hours south to Springfield, where you can dive into the life of Abraham Lincoln. Visit the Abraham Lincoln Presidential Library Museum, tour his former home at the Lincoln Home National Historic Site, and step inside the historic Old State Capitol.

Make a sweet pit stop at Doc’s Soda Fountain in Girard, Illinois, for an old-fashioned root beer float or a giant banana split before continuing your drive to St. Louis. Upon arrival, be greeted by the iconic Gateway Arch, the tallest man-made monument in the United States. This masterpiece of architecture commemorates Thomas Jefferson’s vision of westward expansion. St. Louis also offers a thriving music scene. Explore the Soulard neighbourhood for live music, or enjoy the mix of music, food, and culture in the trendy Loop district. Discover live Blues, Soul, and R&B at legendary venues like Blueberry Hill—where Chuck Berry performed—or The Beale on Broadway. Don't miss the National Blues Museum, which dives deep into the roots of American music.

Head south along the scenic Great River Road, following the Mississippi River to the musical heart of Memphis. Here, music history comes alive. Tour the legendary Sun Studio, where B.B. King, Elvis Presley, and other greats recorded their first hits. For a deeper dive into Elvis's life, explore the opulent Graceland estate. Memphis’s soul shines at the Stax Museum of American Soul Music, home to memorabilia from icons like Otis Redding and Isaac Hayes. Stroll down Beale Street, where live music fills the air and the scent of barbecue lingers. Savor Memphis classics like dry-rubbed ribs or smoked pulled-pork sandwiches.

Follow the Mississippi Blues Trail to Clarksdale, the birthplace of the Blues, located at the crossroads of highways 61 and 49. Visit the Delta Blues Museum to immerse yourself in the history of this uniquely American genre. Continue south to Cleveland, Mississippi, home to Dockery Farms, where Blues legend Charley Patton once worked. Here, the rhythms of the past still echo in the fields where the Blues was born. In Cleveland, visit the GRAMMY Museum Mississippi for a celebration of musical excellence, with exhibits tracing the history of American music from its roots to modern-day stars.

Travel toward the Natchez Trace Parkway, making a stop in Indianola to visit the B.B. King Museum, where the story of this Blues legend and his impact on music comes to life. As you join the Natchez Trace Parkway, you'll wind through centuries of history, passing antebellum plantations and historic mansions. Arrive in Natchez, the oldest settlement in Mississippi, and take time to tour the beautifully restored antebellum homes that offer a glimpse into the South's complex past.

The final stretch of your road trip takes you to the vibrant city of New Orleans, where the mighty Mississippi River meets the Gulf of Mexico. Along the way, make a stop in Baton Rouge, Louisiana's capital city, to explore its rich history, eclectic culture, and renowned cuisine. Once in New Orleans, immerse yourself in the city’s unique blend of history, music, and culture. Wander through the French Quarter, photograph the colourful cottages, and explore the city's famous cemeteries on a guided tour. At Preservation Hall, enjoy an intimate performance of traditional New Orleans jazz, or venture to Frenchmen Street for a lively night of music at clubs like The Spotted Cat Music Club. No visit to New Orleans is complete without indulging in its culinary delights—from sugar-dusted beignets to spicy jambalaya and Andouille sausage. Whether you're drawn to the music, the food, or the historic charm, New Orleans is the perfect finale to your journey.

Drop off your rental car today. New Orleans is a very walkable city so you will not need your wheels here.

After an unforgettable road trip through America's heartland and soul, head to New Orleans International airport and prepare for your departure flight.