Planning Chicago to New Orleans road trip and looking for best places to stop along the way?
This road trip from Windy City to the Deep South is one of our favorites.
Love music? Then you should definitely do this iconic road trip!
Listen to live music in Chicago and St. Louis and explore the blues music on Beale Street in Memphis….
….drive the Blues Highway and visit honky tonk bars on Music Row in Nashville…
….off course, and listen to New Orleans jazz on Frenchmen Street!
Here are some of the best stops on the Chicago New Orleans road trip.
Things to do in Chicago
Located on the shores of Lake Michigan, Chicago is a beautiful city.
If you are new to Chi-town, take some time to explore Chicago’s iconic attractions.
Visit Millenium Park, home to the popular Bean sculpture, and the Art Institute of Chicago.
Take a walk on Navy Pier or enjoy a ride on the Ferris wheel.
For some fun shopping head to the Magnificent Mile.
Eat some deep-dish pizza and then drive south for an iconic road trip.
Chicago to New Orleans via I-55
The road trip along I-55 from Chicago to New Orleans is a great way to see some of the Midwest and the South.
Springfield
The first stop on the road trip is Springfield, IL.
This city is home to the Abraham Lincoln Presidential Library and Museum, as well as several other historical sites.
If you are a fan of the 16th president, make sure to visit this museum.
St. Louis
Just across the Mississippi River from Illinois, St. Louis is an easy stop on your road trip
Visit the iconic Gateway Arch National Park or take a ride to the top for some amazing views.
If you are a baseball fan, catch a Cardinals game at Busch Stadium.
Visit the Museum of Westward Expansion or walk through the Butterfly House at the Missouri Botanical Gardens.
Take the kids to see the Saint Louis Zoo which is home to more than 700 species of animals.
Memphis
The home of the blues, Memphis is a must-stop on any road trip through the South.
Visit Beale Street and explore the history of blues music.
Tour the iconic Sun Studio and the famous Blues Hall of Fame.
Be sure to book your Sun Studios tour in advance as they get full early on.
Check out Graceland, the home of Elvis Presley.
Visit the National Civil Rights Museum, the site of Martin Luther King, Jr’s assassination.
Learn about music history as it was created at the Stax Museum of American Soul Music.
If you are in town on a Saturday, head to the Memphis Farmers Market for local produce and goods.
Jackson
From Memphis, drive south to Jackson, MS.
This city is the capital of Mississippi and home to several interesting attractions.
Visit the Governor’s Mansion, the state capitol building, and the Mississippi Museum of Natural Science.
Take a walk down Capitol Street and enjoy the unique architecture of this historic city.
Natchez
From Jackson, take the historic Natchez Trace Parkway west to Natchez.
This stretch will take you deep through the Mississippi Delta.
This city is home to several antebellum mansions, as well as the Natchez National Historical Park.
Visit Longwood, one of the largest octagonal houses in the country.
Explore Stanton Hall, an opulent Greek Revival mansion.
For a look at Natchez’s African American history, visit the Forks of the Road slave market site.
New Orleans
The final stop on this road trip is New Orleans.
This city is known for its jazz music and Cajun food.
Explore the French Quarter and enjoy the unique architecture of this historic district.
Take a walk down Bourbon Street and listen to some live jazz music.
Visit Jackson Square and the St. Louis Cathedral.
Sample some of the local cuisines at one of the many restaurants in the city.
Visit the City Park or take a ride on the streetcar.
End your trip by listening to some New Orleans jazz on Frenchmen Street!
Chicago to New Orleans via I-65 & I-20
Another option for your road trip from Chicago to New Orleans is to take I-65 south through Kentucky and then I-20 east through Mississippi.
This route will take you through some of the scenic countrysides of the Midwest and the South.
Indianapolis
The first stop on this road trip is Indianapolis, IN.
This city is the capital of Indiana and home to several interesting attractions.
Visit the State Capitol building and the Soldiers and Sailors Monument.
Explore the Indianapolis Museum of Art or take a walk through White River State Park.
If you are a racing fan, catch a race at the Indianapolis Motor Speedway.
Louisville
The next stop on this road trip is Louisville, KY.
This city is home to the Kentucky Derby, as well as several other interesting attractions.
Visit Churchill Downs and take a tour of the historic racetrack.
Explore the Frazier History Museum or walk through the Waterfront Park.
For a taste of local culture, head to the Louisville Slugger Museum.
Nashville
The next stop on this road trip is Nashville, TN.
This city is known as the country music capital of the world.
Music City is also the largest city in Tennessee and is great to visit for couples.
Visit the Country Music Hall of Fame and learn about the history of country music.
Take a walk down Music Row and see where some of the biggest stars in music got their start.
If you are a fan of country music, be sure to catch a show at the Grand Ole Opry.
Tour the Johnny Cash Museum and eat some Nashville hot chicken.
Also Read: Nashville Itinerary
Franklin
Take the scenic drive from Nashville to Franklin and explore this charming small town in Tennessee.
Visit the Carter House and the Lotz House, two historic homes from the Civil War.
For a taste of local culture, head to the Main Street Festival or the Franklin Art Scene.
Birmingham
The next stop on this road trip is Birmingham, AL.
This city is home to several interesting attractions.
Visit the Civil Rights Institute, the Birmingham Museum of Art, and the Birmingham Zoo.
Take a walk through Railroad Park or enjoy a meal at one of the city’s many restaurants.
New Orleans
Your final destination is here!
Spend 2 to 3 days in New Orleans to explore all that the Crescent City has to offer.
Visit the French Quarter, Jackson Square, and the St. Louis Cathedral.
Listen to some live jazz music and eat iconic Cajun dishes such as gumbo and crawfish.
Take a streetcar ride to Garden District or visit one of the city’s many parks.
Things to do in New Orleans
At the end of your trip lies New Orleans, a soulful city that makes visitors fall in love with its culture and history.
Take a jazz cruise on the Mississippi River.
Explore the architecture and eclectic shops in the French Quarter, the city’s most popular attraction.
Tour the historic mansions in Garden District.
Eat beignets at Café Du Monde and try the turtle soup at Commander’s Palace.
Take a day trip to see the historic River Road plantations including Oak Alley Plantation and Laura Plantation.
The Chicago to New Orleans drive is full of amazing attractions and lively cities!
There are so many amazing things to see and do on the Chicago to New Orleans drive, it’s hard to choose a favorite.
What is your favorite stop on this road trip?