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New Orleans to Chicago: Undiscovered Arkansas & Louisiana

New Orleans to Chicago: Undiscovered Arkansas & Louisiana

USA

16 days / 15 nights


Fly Drive Holiday
Guide Price £1,845 per person (based on 2 adults sharing)
Fly Drive Holiday
Duration: 16 days/15 nights

From the soulful south to the towering skyscrapers of Chicago, get off the beaten track on this fantastic fly drive through some of the hidden gems of Arkansas and Louisiana. Experience delicious creole cuisine, rhythm & blues music and stunning countryside as you journey north through the USA.      

Highlights:
  • Sumptuous Cajun and Creole Food
  • Stunning hikes to Flatside Pinnacle and the Ozarks
  • An array of amazing live music venues
  • Immerse yourself in moving civil rights history
  • Experience the buzz of New Orleans
Economy

from £1,845

per person (based on 2 adults sharing)
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Itinerary

Day 1 Arrive New Orleans                
Land in the ‘Big Easy’ and open your eyes and ears to the sights and sounds of this vivacious city.                

Days 2-3 New Orleans  
Dive into soulful N’awlins and explore the historic French Quarter. Walk through the cobbled streets and gaze up at the iconic, intricate iron balconies above, laden with hanging baskets. Listen to blues, soul and jazz music pouring out from every venue on Bourbon Street and enjoy an authentic steamboat dinner cruise on the Mississippi for that true southern experience.                

Day 4 New Orleans to Lafayette            
Pick up your car and set off towards Lafayette, the ‘Happiest City in America!’ Stop off at the state capital of Louisiana, Baton Rouge aka “Red Stick” and see the castle-like structure of the old state capital building before continuing your journey.

Day 5 Lafayette                  
Let the good times roll! Lafayette boasts a distinct culinary identity as the epicentre of Cajun & Creole cuisine that’s earned it the title ‘Best Food City in the USA.’. Be sure to visit Avery Island, the home of Tabasco, and learn about the history of this famous hot sauce! In the evening, check out some live Zydeco music - a popular genre of southern Louisiana that combines tunes of French origin with elements of Caribbean music and the blues.                

Day 6 Lafayette to Natchitoches    
Head across to Louisiana’s oldest city, Natchitoches (pronounced Nack-a-tish!), the original French colony in Louisiana. Walk through the charming old town and down Front Street, the jewel of the city with a distinctly European feel. ‘Steel Magnolias’ was filmed here and fans of the classic 80s movie can take a self-guided tour to spot familiar filming locations.  

Day 7 Natchitoches to Shreveport      
Tucked away in the pocket of northwest Louisiana, Shreveport and neighbouring Bossier City are rich with Cajun character and influences from neighbouring Texas. Make sure to treat your tastebuds to some Cajun-style seafood, po-boys and gumbo, then perhaps your luck at one of the riverboat casinos or listen to live jazz at the Noble Savage Tavern.

Day 8 Shreveport to Hot Springs              
Cruise along the lush ‘Scenic 7’ highway and enter Arkansas. Perhaps break your journey at Murfreesboro where you can try your hand at diamond mining. Anything you find is yours to keep so hopefully you’ll be a little richer by the time you arrive at your next stop, Hot Springs! Take a stroll down historic Bathhouse Row where you can relax in the famous natural thermal waters the town is named after.  

Day 9 Hot Springs to Little Rock        
Start your morning by exploring the stunning, flower strewn Garvan Woodland Gardens before setting off towards Little Rock. On arrival, pay a poignant visit to Little Rock Central High School Historic Site, where the “Little Rock Nine” fought for desegregation in a pivotal act for the USA civil rights movement.    

Day 10 Little Rock          
Take a drive an hour outside of Little Rock into the great outdoors, where you can hike the picturesque Ouachita Trail to Flatside Pinnacle. It’s a short but steep climb to the top of this rocky outcrop but offers one of the best views in the entire Ouachita Mountains (especially at sunset!). Once back in the city for the evening, visit the legendary live music venue, the White Water Tavern. Run in the spirit of classic southern juke joints and honky tonks, it has hosted some of the US’s best country musicians.                

Day 11 Little Rock to Fayetteville      
Fayetteville is the known as the entertainment capital of Northwest Arkansas and its heartbeat is found on Dickson Street. Particularly renowned is George’s Majestic Lounge, the oldest and longest-running club and live music venue in Arkansas.    

Day 12 Fayetteville                  
Start early today and drive to the jaw-dropping Ozark Mountains. Hiking opportunities abound in this pristine wilderness: pass huge boulders and cascading waterfalls on Whitaker Point Trail until you reach magnificent vistas from Hawksbill Crag, or conquer the creeks and caverns of the Lost Valley Trail.    

Day 13 Fayetteville to St Louis                  
Stop for brunch this morning in Bentonville, paying a visit to the Walmart Museum to learn all about this integral piece of the American landscape. After a day’s driving, arrive into St Louis and check out the Gateway Arch - take a tram all the way to the top to admire the city views.        

Day 14 St Louis to Chicago    
Get your kicks on Route 66 as you drive a portion of the iconic “Mother Road” today. Break up the journey in Springfield and visit Abraham Lincoln Presidential Library, grabbing a bite to eat at the Cozy Dog Drive In before arriving in Chicago.  

Day 15 Chicago            
Take in some of Chicago’s iconic architecture in wonderful Millennium Park. Soak up the iconic skyline from the top of the Willis Tower and then explore the largest Natural History Museum in the world, The Field Museum. Finish the day off with some fantastic food at one of Chicago’s award-winning restaurants.    

Day 16 Chicago                
Enjoy some last-minute shopping on the Magnificent Mile before catching your flight back to the UK.  

Map

New Orleans to Chicago: Undiscovered Arkansas & Louisiana

Price & Inclusions

Guide Price £1,845 per person (based on 2 adults sharing)

Inclusions
  • 13 days Alamo Inclusive Compact car hire including 24-hour Roadside Assistance and no surprise compulsory charges on pick-up. A one way drop-off fee is payable locally
  • 15 nights 3★ to 4★ accommodation
  • Dinner & Jazz Steamboat Cruise
Exclusions
  • International flights not included

  • New offers every day!

    We negotiate new offers daily from discounted flights, tours and vehicle hire to free upgrades, added value and unique inclusions. Please call for our latest offers.

    The tour itinerary, inclusions and departures are based on travel from 01/01/2026 to 15/11/2026. For holiday guide price terms and conditions, click here.
    Itinerary distances on this fly drive holiday have been planned around a comfortable driving pace, allowing ample time for stops to enjoy the sites and views along the way. It can be easily adapted taking into account your interests and the pace you prefer to travel.

    Flights

    As we can offer you such a flexible choice of flights, we don't include international airfares with our tour prices. The price you pay will be determined by the time of year you travel, your departure airport, airline and availability.

    Your Trailfinders Travel Consultant will be able to find the best flights to suit you and your choice of tour. Contact us for our latest flight offers or take a look at our flights pages for a general idea of prices.

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