Interstate 65 Road Trip From Chicago to New Orleans

Discover America’s Heartland on I-65

Driving from Chicago to New Orleans along the Interstate 65 corridor is one of the great USA road trips for Kiwi travellers who want a real slice of America. This route links the skyscrapers of the Midwest to the soulful streets of the Deep South, passing through classic college towns, music cities, and quiet rural communities along the way. You get big-name highlights like Chicago, Nashville, and New Orleans, plus places most New Zealanders only hear about in songs and movies.

At Travel USA, we plan this as a Chicago to New Orleans trip, even though I-65 technically runs from Gary, Indiana to Mobile, Alabama. That way, it sounds like the exciting city-to-city adventure it really is, with smart detours that keep you off bland stretches of highway. We usually suggest 7 to 14 days, depending on how often you want to stop. Spring and autumn are ideal for comfortable driving, though summer works if you do not mind the heat, and the route suits couples, friends, families, music fans, sports lovers, and anyone keen on good food and American history.

Starting Strong in Chicago and the Midwest Gateway

For New Zealanders, Chicago is an excellent starting point. You typically arrive via connecting flights through cities like Los Angeles, San Francisco, or Houston, then straight into Chicago. After a long-haul trip from Aotearoa, we like to build in at least two nights here so you can reset your body clock, you could easily stay here for a week with Chicago being one of the tops cities in the States, but totally up to how long a holiday you are wanting. Then get your first feel for driving on the opposite side of the road on your first leg of the trip.

Chicago rewards that extra time with a mix of iconic sights, local flavour, and memorable experiences. Many Kiwi travellers enjoy an architecture river cruise along the Chicago River, wandering through Millennium Park to see Cloud Gate, better known as “The Bean,” or sampling classic deep-dish pizza at one of the city’s long-running pizzerias. Navy Pier is another highlight, with its towering Centennial Wheel offering stunning views over Lake Michigan, and a lively boardwalk filled with entertainment, restaurants, and museums. Evenings can be spent in a blues club soaking up live music, stepping onto the glass floor ledges of the Willis Tower for thrilling skyline views, or catching a sports game if the timing lines up, whether it’s the Cubs, Bulls, or Bears.

When you are ready to drive, it is a short hop from Chicago to Gary, Indiana, where I-65 actually begins. Nearby, Indiana Dunes National Park along Lake Michigan can be your first nature break, with sandy beaches and walking options that feel surprisingly peaceful this close to a major city. From there, your first proper driving leg can run down into Indiana, where Indianapolis makes a logical first stop.

Indianapolis has a strong motorsport story, a growing craft beer scene, and plenty of museums. Families often appreciate the city’s kid-friendly attractions and open green spaces, while adults like the relaxed downtown and easy parking. We can space your first day’s drive so it does not feel like a marathon after the long-haul flight.

Music, History, and Southern Flavours Through Kentucky and Tennessee

Once you leave Indianapolis, the road to Louisville marks the start of that slow shift toward the South. The scenery turns to rolling farmland, small towns, and, as you cross into Kentucky, hints of horse country. Louisville itself blends riverfront history with a confident, modern food scene that many Kiwi visitors are pleasantly surprised by.

Highlights in Louisville include the Muhammad Ali Centre, celebrating the life and legacy of the city’s most famous son, and the Louisville Slugger Museum & Factory, where you can see baseball bats being made and even hold replicas used by major league stars. Sports fans and history buffs alike enjoy a visit to Churchill Downs and the Kentucky Derby Museum, while those wanting a taste of local flavour can explore bourbon distilleries and enjoy guided tasting experiences that showcase Kentucky’s iconic spirit.

From there, continuing down I-65 to Nashville is one of the highlights of this route. The mood changes again as you reach Tennessee, and the city’s music identity hits you quickly. Broadway’s honky-tonk bars, the Grand Ole Opry, and the Country Music Hall of Fame are obvious favourites, but there is much more like the famous RCA Studio B and neighbourhoods like The Gulch and East Nashville to explore.

Some travellers want to keep to the main highway, while others prefer to step slightly off it. Just off I-65 you can reach places like Mammoth Cave National Park for cave tours and walking, or small music-oriented towns where the pace is slower and the crowds are lighter. Because we build each itinerary by hand, we can match the number of stops and the style of stays to how you like to travel, whether that is cozy inns or central city hotels.

Deep South Culture From Alabama to the Gulf Coast

South of Nashville, the road into Alabama brings warmer air, pine forests, and a sense that you are firmly in the Deep South. The history here is powerful, especially around the civil rights movement, and many Kiwi travellers tell us these sections are some of the most thought-provoking days of the trip.

On I-65, Birmingham and Montgomery stand out for their museums, memorials, and historic churches. In Birmingham, the Birmingham Civil Rights Institute and the 16th Street Baptist Church offer a moving insight into the struggle for equality, while the Barber Vintage Motorsports Museum provides a different cultural highlight. Montgomery continues the story with the Legacy Museum and National Memorial for Peace and Justice and the Rosa Parks Museum, allowing visitors to reflect on the people and events that shaped modern America. We plan itineraries so travellers have enough time to absorb these experiences without feeling rushed, balancing historical content with local food, parks, and music along the way.

At the southern end of I-65, you reach Mobile, near the Gulf of Mexico. This charming coastal city, with oak-lined streets, a historic downtown, and plenty of seafood, is a perfect place to linger for a night or two to slow down after busy inland cities.

That final drive across to Louisiana introduces you to wetlands, waterways, and a different kind of Southern culture. We help you decide how to split your time, perhaps one night in Mobile for coastal charm and several nights in New Orleans for music and food. The idea is to arrive in New Orleans with enough energy left to enjoy it properly, not simply tick it off at the end of a long drive.

Crafting Your Ideal Chicago to New Orleans Road Trip

There is no single “right” way to drive this route. Some travellers like a fast point-to-point run with two or three big city stops and longer driving days. Others prefer a slower, more immersive style, spending extra nights in places like Louisville or Nashville, and adding overnights in smaller towns for a feel of everyday American life.

A few popular themes we often build USA road trips around on this corridor are:

• Music and nightlife, linking Chicago blues, Nashville country, and New Orleans jazz 
• Family fun and nature, with city attractions, national parks, and relaxed driving days 
• American history and civil rights, focusing on museums, memorials, and local guides 
• Sports and bourbon, blending games, stadium tours, and tasting experiences 

Practical details matter when self-driving across the USA. You’ll want the right vehicle for your group and luggage, whether that’s a compact sedan, a mid-size SUV, or something larger, and an understanding of which hotels provide convenient parking options. Driving distances should also be planned so each day on the road is manageable, with the right number of nights in key locations to avoid rushed stays.

Some practical tips we recommend for Kiwi travellers include:

• Choosing the right vehicle size for your group and luggage, from a compact sedan to an SUV
• Planning driving distances so no day feels too long behind the wheel
• Pre-booking city hotels with convenient parking options
• Timing big-ticket experiences like games, concerts, or tours
• Considering major US public holidays and long weekends to avoid busy roads and sold-out experience

Because we are New Zealand-based and focused solely on American itineraries, we understand Kiwi travel patterns and can align drives, stops, and experiences so your first day on the road is realistic and stress-free.

Plan Your I-65 Adventure with Travel USA

The Chicago to New Orleans route that loosely follows I-65 belongs on every list of memorable USA road trips. You get towering city skylines, college sports, bourbon and barbecue, moving civil rights history, and finally the jazz and food culture of New Orleans. The change in accents, scenery, and flavours as you drive south is part of the appeal, especially for Kiwi travellers used to shorter distances at home.

As you think about this trip, start with your travel style. Do you want late-night music and long city stays, or early starts and quieter small towns? Are you most excited by food, history, live music, or family-friendly attractions? Once you have a rough sense of your must-do experiences and preferred dates, we can turn “Chicago to New Orleans” from a vague idea into a day-by-day itinerary that feels personal, realistic, and full of the kind of memories that stay with you long after you roll into New Orleans for that final plate of beignets and a night of live jazz.

Turn Your USA Road Trip Ideas Into a Tailored Itinerary

Ready to put your route, budget, and must-see stops into a clear, stress-free plan? Explore our curated USA road trips and let Travel USA customise the details so you can focus on the journey, not the logistics. If you have questions or want a little expert guidance before you book, simply contact us and we will help you map out your ideal adventure.