So just one month today I will be celebrating St Patrick’s day in Chicago!
My friend and old work bestie Clare (who you may remember from my Cambodia trip), and I are flying in to Chicago for the weekend before picking up the hire car and doing a Chicago to New Orleans roadtrip via some pretty epic cities!
Seeing as it’s pretty close now, I figured I’d tell you all about what we’ll be doing and our itinerary for the roadtrip…
Also, make sure you read to the very end to find out if we enjoy the trip and whether we’d change about the itinerary!
Ready to find out what my ultimate Chicago to New Orleans roadtrip itinerary includes? Let’s go!
Chicago – 2 Nights
So before our Chicago to New Orleans roadtrip begins, we have a weekend in Chicago celebrating St Patrick’s Day before we start the proper roadtrip, and are basically going to spend our time there eating deep dish pizza, and drinking plenty of Shamrock shakes from Maccas.
We’re excited to stay at the Langham Chicago, explore the city, and I’m especially excited to see the building on Michigan Avenue where one of my Great Uncle’s worked in the 1930s (he was a travelling salesman selling Sniders Catsup (Ketchup) – so glam).
St Louis – 1 Night
We’re mostly stopping in St Louis to break up the longer journey between Chicago and Nashville, and to drive part of Route 66.
The old Route 66 from Chicago to St Louis includes the town of Pontiac where there’s a museum, and numerous cute little diners and old gas stations perfect for the ‘gram.
There’s also Abraham Lincoln’s Tomb in Springfield, and the Presidential Library!
In St Louis itself we’re gonna be super morbid and visit Tennessee Williams’ grave, as the whole reason we’re driving to New Orleans is to attend the Tennessee Williams Literary Festival (yes, we are total geeks).
Nashville – 3 Nights
And then it’s on to Nashville for the next stop on our Chicago to New Orleans roadtrip!
I actually visited Nashville when I was 14 and fell in love with it so am crazy excited to be back in this awesome city.
We’re staying at the stunning Hermitage Hotel and are gonna spend a few days just soaking up all the country music and fried chicken and enjoying all of the street art that the city is famous for.
I’m also looking forward to going back to Tootsie’s Orchid Lounge and BB Kings, an we also have a concert at the Grand Ole Opry booked in!
Read: Three nights in Nashville, Tennessee
Memphis – 3 Nights
Memphis is another place I visited when I was 14 (my family did a roadtrip from Atlanta to Nashville, Memphis, Vicksburg, and New Orleans), and so I’m really looking forward to going back and being able to go to the bars and drink actual cocktails rather than mocktails haha.
We’re staying at the Peabody Hotel (the one with the famous ducks!) and are planning to do lots of cultural stuff in Memphis, with plans to visit Stax Museum of Soul, Sun Studios, the Civil Rights Museum and Lorraine Motel, and of course Elvis Presley’s Graceland.
Jackson & Natchez – 2 Nights
Jackson is a quick one night stopover on the way through to Natchez, but we’re gonna make sure we visit the Old Capitol Building and the Mississippi Civil Rights Museum.
After Jackson we’re driving down to Vicksburg and then Natchez for a one night stay at Monmouth Historic Inn.
Both towns are famous for their involvement in the Civil War and have bags of history so we’ll be doing ALL the historical things!
On our way to New Orleans we’re also planning to stop off at the Oak Alley Plantation to try and learn a bit more about the enslaved people who lived there, as they apparently have a really informative exhibit which is quite rare for a plantation as most try to keep quiet about their past.
Read: Driving Through Mississippi: Jackson, Vicksburg, & Natchez
New Orleans – 4 Nights
And finally, we’ll be arriving in NOLA, where we’re spending four nights!
We begin our New Orleans part of the trip with dinner at The Commander’s Palace, one of the city’s most famous restaurants.
Then we’ll be geeking out at the Tennessee Williams Literary Festival, eating beignets, jambalaya, po’ boys, and creole dishes, and drinking cocktails every night in New Orleans’ numerous jazz bars.
We’re also planning to go for a cruise on the traditional showboat, Natchez, and see a Basketball game! And then it’s time to fly back to London.
Crazy excited for our Chicago to New Orleans roadtrip!
I’ve never done a huge roadtrip like this in the United States before without my parents, and honestly with all the crime and shootings etc and huge roads I am slightly nervous.
But we’re gonna make sure we stay vigilant and don’t go driving around after dark, and the excitement I have for this trip is WAY higher than the nerves.
Obviously I’ll be writing loads of blog posts on the roadtrip and our experience, as well as posting lots on Instagram, so follow along and keep an eye out 😉
Post-Trip Update
So, we’re back from the trip!
And did we enjoy it? HECK YEH.
You guys, it was actually amazing. Probably one of the most incredible trips I have EVER done.
I honestly want to cry it was so perfect and now I’m desperate to do it all over again! The itinerary worked perfectly, we had the ideal amount of time in each place, and I’m now recommending it to eeeeeveryone I meet.