Chicago to New Orleans: a road trip through the musical heart of America

New Orleans Spotted Cat Jazz bar — *The Spotted Cat. My favorite jazz bar in New Orleans.*

I’ve mentioned this before: traveling and live music are two of my favorite things to do in life. So early this year, I started playing with the idea of a new road trip, this time centered around some of the most iconic music cities in this country – from Chicago, the place I currently call home, to New Orleans.

You can either click here to get to the daily posts with all sort on additional info about my trip – where I stayed, what I ate, what I saw – or here if you want to read all the daily postcards in one go. Or here if you need help planning this road trip.

Or just keep scrolling.

A road trip that took me through six different states: I’ve been to Illinois, Indiana, Kentucky, Tennessee, and Louisiana before; however, it was my very first time in Mississippi. The trip involved staying in major cities such as Nashville and Memphis, as well as small towns like Clarksdale, Greenville, and Natchez.

Postcards from a Chicago to New Orleans road trip

Day 1: Chicago, IL to Indianapolis, IN

I left a beautifully sunny Chicago later than expected – due to the car rental agency, well, momentarily not having any cars available to rent – driving slightly north from downtown to catch Lake Shore Drive at its most iconic stretch, right between Lincoln Park and Oak Street Beach, determined to drive as close to the lakeside as possible until reaching the Ogden Dunes.

From there, it was an almost straight drive south through rural Indiana. Maybe not be the most interesting place on Earth, but the drive was smooth, the traffic nonexistent, and everything looks prettier when it’s sunny, right?

A total of 223 miles, unhealthily ended with what I was told is the unofficial “Hoosier” obsession: a breaded pork tenderloin sandwich. Not the simplest thing to digest after a six hours drive, but nothing one or two well-deserved local IPAs can’t wash down. Make it three.

Also: driving with the sunroof open and getting sunburnt on day one: done.

indianapolis motor speedway — *The Indianapolis motor speedway*

Day 2: Indianapolis, IN to Louisville, KY

I took it easy in the morning, leaving after 10 am, which was not my brightest idea ever, given the heat I drove through all afternoon.

A few miles past Indianapolis, bored with the straight and uneventful state roads, I started improvising, hitting random county roads – a few of which were unpaved – much to the utmost disappointment of the mighty GPS, which was forced to re-route every other time.

The closer I got to Kentucky, the browner the fences became, the whiter the houses, the pinkier the trees, the smoother the rolling hills were, the more numerous the horses, and, to my happiness, the bourbon distilleries.

Disclaimer: writing this slightly hungover after a couple of world-class bourbon tasting experiences last night.

Louisville bourbon tasting — *Bourbon tasting in Louisville*

Day 3 and 4: Louisville, KY to Nashville, TN

The drive began with a bit of traffic leaving Louisville and ended with a bit of traffic approaching Nashville. In between, a slow 214 miles unfolded, including two glorious entries into Tennessee (it turns out, if the GPS says something, it’s most likely right), driving on beautiful, tiny roads surrounded by lush vegetation, farms, and livestock.
And I believe I was the only person not driving a pickup in all of Tennessee.

Nashville, AKA Music City.

Music all day long, music all night long; neon lights, crowded streets, cowboy hats, leather boots, short shorts, booze, cold beers, warm whiskey all around me on Broadway. An unpleasantly humid and warm Monday night. The gigantic BBQ ribs dipped in spicy sauces I’ve had might have contributed to intensifying the perceived heat. Wearing my leather jacket was not helping either. It’s an unnecessary piece of attire, but it is required by this movie script. So be it.

The first morning off from driving, I left the craziness of downtown – already buzzing with music and booze – for a much-needed chill walk around the quieter neighborhood of Germantown, taking a break for a heartwarming, mouthwatering family-style dining experience at Monell’s: sharing table, stories and homemade southern food with other guests. A calm and relaxing morning after last night’s shenanigans before finding myself a bit discouraged back in the sinful madness of Broadway, thinking the 20-30-year-old me would have appreciated this place more.

“I guess I’m aging,” said the man in black, writing this from a honky-tonk bar, listening to some good old Johnny Cash, while sipping yet another Jack on the rocks, with no intention of going back to his motel anytime soon. The weatherman says it is about to start raining after all.

Nashville Broadway — *The Broadway in Nashville at night*

Days 5 and 6: Nashville, TN to Memphis, TN

It turned out the weatherman was right. The rain came copiously all night long, stopping just a few minutes before I left the motel. The first 150 miles were as smooth as it gets, mostly driven along an empty Natchez Trace Parkway with a pale sun trying to make an appearance. My only worry was not to run over the pretty naive, turkey-looking-like birds attempting to cross the road without any notice.
When a tiny little screw somehow found its way into the right rear tire of my car, everything changed, and a rather pleasant morning turned into a wasted afternoon. After four hours of pointlessly waiting in the middle of nowhere for the prepaid road service, I decided to man up and change the tire myself.
I arrived in Memphis late at night, only to have the very digital and comfy, yet rather boring, Hyundai replaced by a way more analog, a bit rough, but more fun-to-drive Jeep.

Pros: I was rewarded with a beautiful, multicolored Tennessee sunset.
Cons: The day was screwed (pun intended), and I went straight to bed.

Memphis: rough, real, reckless, and soulful.

The day off from driving was well spent ticking off boxes: Graceland, Sun Records, the Museum of Civil Rights, Memphis-style BBQ, Beale Street and its blues bars.

In my personal memory lane, it all goes back to a day in the early nineties when, after numerous nights spent at my defining place (hello, @bloom_mezzago ), I purchased an audio cassette: “One Night in Memphis. A Tribute to Otis Redding” which I played on repeat during those foggy nights driving up and down the roads between Milan and the mighty Adda River. That’s when, I suppose, “I got the blues”.

Leaving the blues bar where I am writing this, and heading out of Tennessee to enter Mississippi next: Elvis has left the building, and so have I.

Memphis Sun Studios — *Sun Studios, a must stop in Memphis for music lovers*

Day 7: Memphis, TN to Clarksdale, MS

One of the shortest drives of this trip: 100 miles, which – aside from the very beginning, leaving Memphis – were driven mostly on the old route lying west of the new Highway 61: the original “blues highway.” Not the prettiest landscape, and the gloomy sky didn’t help, but on the flip side, with the temperature dropping significantly, wearing my leather jacket doesn’t make me look like an idiot anymore.

Clarksdale: a tiny, unassuming, and rather deprived city at first glance, hosting a number of iconic, incredible blues bars. After all, the devil’s music was born in the cotton fields around here.

Blues music, Mississippi beers, catfish, fried green tomatoes, fried pickles, a night spent in a shack with a rocking chair on the porch. My accent surprisingly seems to expose and uncover my alien status, but I am obviously trying hard to blend in.

I might buy some overalls and a harmonica. That might help too.

Clarksdale Red Lounge blues bar — *The Red Lounge blues bar in Clarksdale*

Day 8: Clarksdale, MS to Greenville, MS

The landscape didn’t change much from yesterday during today’s short 81-mile journey, while the weather did, becoming more threatening as I approached Greenville. A few miles from the final destination, the rain made a groovy and loud entrance in the form of a nasty thunderstorm. With the water in the roadside fields growing brown and thick, I left the side roads to stay on the, for once, safer highway.

Once in Greenville, given that the only blues bar in town was closed, I compensated for the lack of entertainment with more southern food: the usual catfish and fried veggies were joined by some new additions—okra, boudin balls, crawfish and alligator.

It was an uneventful day, but I still managed to check off two items from my bucket list of places I wanted to see, both of which have significantly marked my life in different ways and at different moments:

Dockery Farms, which is believed to be the place where blues music was first conceived.
Leland, the birthplace of Kermit the Frog.

It explains a lot, I know.

dockery farms birthplace of blues — *Dockery farms, the birthplace of blues*

Day 9: Greenville, MS to Natchez, MS

I left the bed and breakfast at the sunny Belmont Plantation, where I had spent the night, and headed slightly back north for my first encounter with the mighty Mississippi River at Warfield Point. The streets had magically dried out by the time I set off, allowing me to avoid the highways for most of the drive.

I’ve always considered the saying ‘everything happens for a reason’ to be a big load of nonsense that we tell ourselves to get through tough moments in life – and doing so, being totally acceptable. However, driving the unexpectedly unpaved riverbank stretch of the 465 South in a 4×4 was definitely better than if I had been in a full-size . And that only happened because of last week’s flat tire accident, so the joke’s on me, folks.

After a stop in the historic city of Vicksburg, the last 40 of today’s 210 miles were driven on the same Natchez Trace Parkway that I had left a few days earlier in Tennessee. It was the same smooth drive, with the main difference being the absence of the Tennessee crossroad ‘suicidal’ turkeys and the presence of much larger, majestic trees and lush vegetation.

Closing the day with more fried green tomatoes to satisfy my newfound addiction, a gigantic seafood platter, some more live music, a couple of beers, and flowing chatters with other fellow travelers – all while watching a killing sunset over the Ol’ Man River.

Two more sleep to The Big Easy.

*Sunset over the Mississippi river in Natchez*

Day 10: Natchez, MS to Lafayette, LA

Taking the Natchez-Vidalia Bridge meant entering Louisiana, the last state of the road trip.

The first part of the ride, another solitary drive with no other cars in sight for miles, began on the 15S, coasting along the Mississippi – both river and state – and ended with the long unpaved stretch on the riverbank road beside the Atchafalaya River.

About 20 miles before reaching Lafayette, I took an airboat ride experience in one of the largest swamps in the country: brown waters, beautiful trees, friendly alligators, and zero regrets for the fried reptiles I had eaten no more than 48 hours prior. I am just a bad person with a great curiosity for food… Right. Sorry gators.

The airboat adrenaline progressively faded over the 20 more miles I had left before reaching Lafayette, to definitely evaporate in the back garden of a grocery shop where I ended up sunbathing with a seafood po’boy in one hand and a Louisiana beer in the other.

Walking back to the hotel through a neighborhood with bilingual French and English street signs, wooden pastel-colored houses each with a hammock and rocking chair on the porch, and despite it being Monday, I couldn’t help but notice that everyone and everything seemed to be moving slower and taking it easier than I am accustomed to.

Note: If the trees in California forever changed my benchmark for what ‘tall’ means, then the crawfish platter in Louisiana has given a completely new meaning to the expression ‘big portion’.

I might need a night cup.

Lafayette swamp boat — *Taking a boat to visit the swamp around Lafayette*

Day 11, 12 and 13: Lafayette, LA to New Orleans, LA

I left Lafayette during rush hour, but it didn’t feel like it because the traffic was light. Despite this, the ride wasn’t particularly engaging or enjoyable. I am not really sure if this was because of the landscape, which – aside from a few small cities with gorgeous trees – was flat and plain, or because I knew it was the last leg of this road trip through the musical heart of America: 1,692 miles, 11 days, 8 live music shows and lots of food after leaving Chicago, I returned the car in New Orleans.

Right after settling into the guest house and while waiting for the only concert I had pre-booked, I embraced the Brit in me, entering a 3pm-still-empty pub – true to the saying, “it’s 5 o’clock somewhere” – to down a celebratory cold one. A pianist was working his magic despite the absence of an audience – almost poetic.

From there, it was a night of jazz, crawling from one music bar to another, from traditional to modern styles, indoors and right on the street, making sure to avoid the trashy part of Bourbon Street because, like in Nashville, I just can’t.

The two days since returning the car mirrored each other: late mornings, long walks, getting lost among beautiful houses and majestic trees, dazed and confused partly ‘cause of the overwhelming scents of confederate jasmine and newly blooming magnolia trees, partly ‘cause of the already dense, muggy, and sticky air, mostly ‘cause of the minor hangovers following the late nights’ jazz bar shenanigans.

Then, as nighttime kicked off, it was the jazz all over again.

Adding 8 more live shows to bring the grand total of music seen in the last two weeks to 16. And adding all the Cajun food I could possibly fit in my stomach to bring the grand total of weight I’ve gained since Chicago to I-don’t-wanna-know pounds.

Give me live music, new cuisines, serendipitous encounters, and travel, and you can be sure that you’ll see the happiest version of me..

Once again: greens and vegetables for the next two weeks.

New Orleans Garden District — *Beautiful houses in the Garden District*

Planning a Chicago to New Orleans road trip

I began my research around March and decided to plan the trip for the end of April. This timing minimizes the risks of flooding, which are higher just before due to snow melting in the Midwest and after due to the increased chances of storms and tornadoes. One of my main requirements was to be in certain cities on specific days, ensuring that both the venues I wanted to visit and the restaurants I wanted to try were actually open. It took a bit of Excel planning, but I managed to organize everything.

For this Chicago to New Orleans drive, I opted not to purchase any maps or special apps this time. Instead, I relied entirely on Google Maps, which has proven to be more than reliable.

Louisville to Nashville County Road — *A beautiful county road between Louisville and Nashville*

How Long is a road trip from Chicago to New Orleans?

The shortest possible road trip from Chicago to New Orleans on the highway is about 928 miles, according to Google Maps. If you factor in all the major cities where I stayed overnight, the total distance increases to 1,273 miles. However, my actual itinerary was even longer—1,692 miles to be exact. I intentionally avoided the main highways as much as possible, opting for county roads and passing through small cities. Along the route, I had several diversions. My longest leg was from Nashville to Memphis (a distance of 261 miles), while the shortest stretch was from Clarksdale to Greenville (only 81 miles).

How long does it takes to drive from Chicago to New Orleans?

According to Google Maps, if you drive without stopping, you can cover the entire distance from Chicago to New Orleans in half a day. In less than 24 hours, you’d pass by all the major cities I’ve visited. But of course, that’s purely theoretical. In reality, my road trip took 11 days, including a few multi-day stops at various places.

My two weeks itinerary on a Chicago to New Orleans road trip

I walked to the car rental downtown on April 13. From there this was the itinerary of my Chicago to New Orleans road trip (A description, map and general information are in each daily post):

My favorite places during my road trip from Chicago to New Orleans

Indianapolis

Aristocrat Pub & Restaurant, 5212 N College Ave, Indianapolis, IN 46220. The location is pretty nice, and parking is super easy. I had the breaded pork tenderloin sandwich with a pint of a local hazy IPA, which was pretty good. It was all I needed after the first day of driving.
Indianapolis Motor Speedway, 4790 W 16th St, Indianapolis, IN 46222. Being born in Monza, where the Italian F1 GP is held, I had to pay my tribute to this sports venue. Although it was closed, you can still get a good view from the outside.
More places between Chicago and Indianapolis here

Louisville

The Eagle, 1314 Bardstown Rd, Louisville, KY 40204, You’re in Kentucky – you have to try fried chicken, right? The one you get at this place is phenomenal.
Taste Fine Wines and Bourbons, 335 W Broadway, Louisville, KY 40202, I decided to have a bourbon tasting experience here because the place was literally 2 blocks from the hotel. They have an incredible selection of different bourbons from all over the country, and the bartender was very competent.
More places between Indianapolis and Louisville here

Nashville

Edley’s Bar-B-Que, 1004 Woodland St, Nashville, TN 37206. While I’m not an expert, I can say that the ribs here were absolutely great. It’s also the first place I had dinner in Nashville a few years ago, and I’m a sucker for memories.
Monell’s Dining & Catering, 1235 6th Ave N, Nashville, TN 37208, This place follows the same concept as one I visited in Savannah a couple of years before. There’s no menu, and you can’t reserve a table. Food is served at pre-set times. Large communal tables seat around 10 people each, where you’ll sit next to strangers. After a few minutes’ wait, the table is covered with a feast of southern food, much like a Christmas dinner at home. The fried chicken was spectacular.
Butchertown Hall, 416 4th Ave N, Nashville, TN 37208, It’s more upscale than Edley’s and offers great brisket and ribs.
Robert’s Western World, 416 Broadway # B, Nashville, TN 37203, a world-famous honky-tonk bar featuring great music and cheap booze.
Tootsies Orchid Lounge, 422 Broadway, Nashville, TN 37203, Another iconic honky-tonk bar, my favorite part is the downstairs area (upstairs can get a bit too rowdy). It’s a bit more intimate than Robert’s.
More places between Louisville and Nashville here

Memphis

Mr. Handy’s Blues Hall, 174 Beale Street Memphis, TN 38103, Easily my favorite blues bar in Memphis, this juke joint is a hidden gem. It’s easy to pass by, but it’s a great place with some real blues.
Charlie Vergos’ Rendezvous, 52 S 2nd St, Memphis, TN 38103. This historical BBQ spot is located in a basement and serves up racks of dry ribs cooked over charcoal. Highly recommended.
Sun Studio, 706 Union Avenue, Memphis, Tennessee, U.S, An iconic recording studio that opened in 1950. The tour of the studio is fun and informative – highly recommended.
More places between Nashville and Memphis here

Clarksdale

The Hollywood Cafe, 1585 Old Commerce Rd, Tunica Resorts, MS 38664. easy to miss and unassuming from the outside. However, it was one of my favorite meals during this road trip. It was my first (and favorite) encounter with fried green tomatoes. The grilled catfish was to die for: traditional Mississippi Delta cuisine at its best.
Red’s Lounge, 398 Sunflower Ave, Clarksdale, MS 38614, the real-deal Mississippi juke joint. It’s a fantastic place and a dream destination for any blues music fan out there.
Shack Up Inn, 001 Commissary Cir Rd, Clarksdale, MS 38614. This quirky place has a slogan ‘The Ritz We Ain’t,’ which sums it up perfectly: an unusual, unique and fun lodging accommodation composed of a number of restored sharecropper shacks built in the shotgun style of the South. I stayed in the Electric Blue Shack. A great experience all around.
More places between Memphis and Clarksdale here

Greenville

Dockery Farms, 229 MS-8, Cleveland, MS 38732, the birthplace of blues music. It’s pretty isolated, you can play some Delta music on the speakers: almost a religious experience.
Jim Henson Delta Boyhood Exhibit, 415 S Deer Creek Dr E, Leland, MS 38756, the birthplace of Kermit the Frog! Can you believe it
The Belmont 1857, 3498 MS-1, Wayside, MS 38780. An incredibly well-preserved 19th-century mansion situated a few miles away from downtown Greenville. The owner, Brad, sits with you at breakfast, explaining the history of the property in detail. It’s an great experience.
More places between Clarksdale and Greenville here

Natchez

Magnolia Grill, 49 Silver St, Natchez, MS 39120, A great little restaurant right on the river. The seafood platter and, once again, the fried green tomatoes were particularly yummy.
Under-the-Hill Saloon, 5 Silver St, Natchez, MS 39120, right next to the Magnolia Grill—a perfect place to end your night with some beer and live music while watching a stunning sunset over the Mississippi River.
More places between Greenville and Natchez here

Lafayette

Olde Tyme Grocery, 218 W St Mary Blvd, Lafayette, LA 70506, the place to go for a Po’Boy sandwich. They recommended the seafood one, and it didn’t disappoint.
The Cajun Table, 4510 Ambassador Caffery Pkwy Suite C & D, Lafayette, LA 70508. Be hungry: it is a crawfish fest. They serve one of the largest platters I’ve ever seen.
Atchafalaya Basin Landing Airboat Swamp Tours, 1377 Henderson Levee Rd, Henderson, LA 70517, a very fun experience. The tour lasts a couple of hours and takes you to various locations in the swamp around Lafayette, where you’ll have close encounters with very friendly alligators.
More place between Natchez and Lafayette here

New Orleans

Fritzel’s European Jazz Pub, 733 Bourbon St, New Orleans, LA 70116. a great jazz bar open night and day. I recommend going in the afternoon when it is less crowded (if not even empty), but be sure: there is always a fantastic musician playing..
The Spotted Cat Music Club, 623 Frenchmen St, New Orleans, LA 70117, Talking about a real experience, this was by far my favorite jazz venue in Nola. Great artists, packed with locals, reasonably priced drinks, open till very late. You can even stay in the little patio outside, sipping a drink while listening to the music coming from inside and watching Nola pass by.
Dooky Chase Restaurant, 2301 Orleans Ave, New Orleans, LA 70119, one of the best meals I’ve had in a while. Great southern food in a legendary Creole premises. Unmissable.
More places between Lafayette and New Orleans here

Lafayette crawfish platter — *The crawfish platter I had in Lafayette*

Where do you stay when driving the from Chicago to New Orleans?

Unlike my previous road trips, I stayed in a motel only once – in Nashville. For all other accommodations, I made choices based on either their location or the uniqueness of the lodging. This included places like a shack, a guesthouse, and even a mansion. Details about the accommodations I used during my Chicago to New Orleans road trip are mentioned in each daily post. each daily post.

How many miles do you need to drive every day and for how many hours

As I said before, I drove 1,692 miles in total. My longest leg was from Nashville to Memphis (a distance of 261 miles), while the shortest stretch was from Clarksdale to Greenville (only 81 miles). Considering stops for pictures, gas, food you might expect to stay on the road for anything between 3 and 8h a day.

How much does it cost to drive from Chicago to New Orleans?

Including everything for this road trip from Chicago to New Orleans I spent about $4,300. Here is how:

$94.10 (but actually free thanks to my Bilt card points) for a one way flight from New Orleans to Chicago with American Airlines
$147 in gas
$753.04 to rent the car in Chicago and return it in New Orleans – including full insurance (note: due to some issues with the road service on day 5, the car rental agreed in refunding me $375. The original price was $1,244)
$1,389 in lodging. The cheapest accommodation was in Indianapolis (at $25 per night, thanks to some accrued discount I had). The most expensive was in New Orleans (at $176 per night).
$130.29 in car sharing services
$1,788 in food, drinks, entertainment, parking etc.

Natchez to Lafayette county road — *An unpaved county road between Natchez to Lafayette*

What type of car is best to drive from Chicago to New Orleans?

For a Chicago to New Orleans drive, I recommend opting for a full-size car, preferably a 4×4. While it might not be necessary in the first part of the road trip, once you reach Mississippi, the risk of flooding or heavy rain makes a full-size or even better a SUV the safest choice. Additionally, if, like me, you decide not to stick to highways but explore country roads, you’ll likely encounter unpaved roads. A 4-wheel-drive vehicle would make the journey more comfortable.

Can you drive from Chicago to New Orleans with an electric car?

Yes, an electric car road trip from Chicago to New Orleans is feasible. However, it requires some additional planning to locate EV chargers along the route. In some areas, particularly in Mississippi, fast-charging networks might not be readily available.