• Casey Kidwell

My 3,321 Mile Cross-Country Roadtrip to Chicago


Well hello there! It's been a while but I'm back y'all! (See what that Southern Living can do to a person. Okay okay I was there two days I would hardly call that living but cut a girl some slack).


As many of you know, I recently returned from a semi cross-country road trip. While the trip itself was bittersweet being that we were driving to Chicago to drop Adam off at school, we were still very much looking forward to the adventure we would experience to get there.


While I originally wasn't actually planning on driving with Adam, it practically slapped me in the face one day like "duh Casey, of course you should!" Thankfully my work schedule allowed me to and we got to planning.


Ultimately, we knew our final destination so it was all about how we wanted to get from Point A to Point B. There are plenty of places in between here (Los Angeles) and Chicago that I wanted to include on the trip (uh hello Antelope Canyon, I see you girl) but unfortunately they weren't feasible to add into this particular trip. We were on somewhat of a timeline after all. So we focused on working with what we had - which btw was pretty darn good.


I'm not the most geographically gifted individual so I definitely had to spend some time looking at my United States map but in no time at all I had crafted the perfect route. Our focus was visiting places we had never been but wanted to see, places that we would be excited to stop and spend time in even if just for dinner and to sleep.


The finalized route was as follows:

Day 1: Los Angeles, California -- Santa Fe, New Mexico

Day 2: Santa Fe, New Mexico -- Austin, Texas 

Day 3: No Driving - Enjoy Austin

Day 4: Austin, Texas -- New Orleans, Louisiana

Day 5: New Orleans, Louisiana -- Nashville, Tennessee 

Day 6: Nashville, Tennessee -- Chicago, Illinois 

Day 1: Los Angeles -- Santa Fe (12 hours)


Well we definitely didn't leave quite as early as I wanted. While we packed the car the night before - life hack people, pack the car the night before - a certain someone, cough cough, had trouble getting out of bed and before you knew it it was after 6am and we were just leaving the house on our way to get coffee.


Right before getting onto the freeway Adam realized that he completely forgot his laptop and book bag at the apartment so back home we went. Might need that.


With laptop in tow, coffee in hand, we were FINALLY ready to hit that dusty trail. Leaving anytime before like noon on the weekends in Los Angeles still just about guarantees that you'll avoid any traffic but we had a lot of driving ahead. Day 1 was officially our longest driving day - roughly 12 hours lay between us and Santa Fe.


Considering how long we were in the car, it was smooth sailing. If I had to describe the first leg in one word it would be HOT. We had decided to be THOSE tourists and get out and take pictures at every sign which in theory was a wonderful idea but considering the climate of some of the places we were driving through, especially on that first day, it was tough to get out of that beautiful air conditioned car. Pants were a bad choice my friends.


We started listening to the podcast Serial, which would be my second tip for a long road trip (after packing the car the night before, remember), find a good podcast, something with multiple episodes that you'll want to listen to for hours...And hours. Crime podcasts are great for that and Serial was our designated road trip podcast.


On the first leg I also started reading "Where the Crawdads Sing" out loud. I know some people have trouble reading in the car or any moving vehicle for that matter, to which I would recommend investing in audio books. It really helps pass the time and you feel so accomplished!


It was dark by the time we arrived in Santa Fe and by dark I mean DARK but we were able to find our AirBnb and our amazing hostess greeted us and showed us to our little guesthouse. We were disappointed to not be able to spend more time at Casa Kachina but it was such a perfect stopping point for our first and longest day.


The room was spacious and cozy and had amazing decorative touches, reminiscent of the traditional art and decor found in Santa Fe.


Since we arrived at nighttime, we were absolutely astonished by the breathtaking scenery behind us when we were greeted by the sun in the morning. It was as if this beautiful collection of guest houses was plopped in the middle of this picturesque desert scene. If only we had more time to take it all in. Santa Fe, we will be back!



Monday was a holiday and we had our second longest day of driving ahead so we only had time to stop for a coffee and some pastries to go but still a great opportunity to seek out the best of the best that Santa Fe had to offer.


The night prior, we looked up "Best Coffee" or "Best Cafe," "Best" something or other and came across husband and wife owned, Clafoutis. We popped in for coffee and to see what all the buzz was about. Even at 8am, the place was already packed with guests.



I found myself mesmerized by the owner speaking French to a customer in front of us and then was immediately overwhelmed by all the choices in front of us. We decided to take a Pain Au Chocolate, a sampling of three Beignets and an Almond Croissant and two Americano's and hit the road. Believe me when I say, that is by far the second best Almond Croissant I've ever had - the first still belongs to that hole in the wall French Bakery in Breckenridge.


Day 2: Santa Fe -- Austin 

Back on the dusty trail for day two of driving, our second longest day, close to eleven hours out on the open road. The terrain didn't change much between day one and two but it was still beautiful nevertheless.


Miles upon miles of lush green grass and rolling hills, cows grazing out in the open, and the bluest skies filled with the fluffiest clouds you could ever imagine. There's something so magical about the open road isn't there?


Today was filled with plenty of reading and listening to our podcast and unfortunately not much beyond that. We stopped at Pizza Hut for dinner as we were still about two hours outside of the city and knew nothing would be open for dinner by the time we landed. This way we could eat and then crash into bed when we arrived to our AirBnb a couple hours later.



Day 3: Exploring Austin! 

Boy am I glad Austin was the city we decided to spend the most time - what a fun town!

I forgot to mention our AirBnb...We were both SO excited to have found an Airstream in Austin, something we've always wanted to experience. While the description of the location mentioned the "up-and-coming" nature of East Austin, I would beg to differ. It is FAR from up-and-coming, at least the part we were in.


The pictures on AirBnb also failed to show all the surroundings of the Airstream like the fact that it was parked in someone's driveway and at that back of that driveway was an old run down shed with an old run down truck in front of it. Yeah, not the most aesthetically pleasing nor was it the luxury Airstream of my dreams. Sigh.


Nevertheless we were only there two nights so we would survive (and make sure to spend all of our time outside the Airstream). That wasn't hard at all considering how much there was to see in the city!



Our first stop was Mañana for coffee. I could have literally been walking into a coffee shop in Los Angeles it was so trendy and cute and filled with freelancers and people working away on their laptops. I noticed immediately all the dogs here too which made me happy to know Austin is in fact a very dog friendly city.



We took our coffee to go as we had plenty to walk around and see on South Congress Street. There were honestly so many amazing gems along this one street, many of which I'm sure we didn't even see but nevertheless I'm going to list each below with a little description so I don't ramble on and on about them.



Kendra Scott Flagship -- The most beautiful store I've ever set foot in in my life. The decor is so intentional and beautiful I wanted to buy something simply because I felt so inspired everywhere I looked.



Mi Casa -- Souvenir shop filled with great, traditional, South of the Border souvenirs.


Parts and Labour -- Super unique store filled with gifts hand-crafted by local artists. It also had a gallery at the back with artwork for sale. I purchased some succulent prints to feature in my gallery wall in my room at home.



Co-Star -- Boutique with lots of cute trendy clothes for men and women. This place had incredible t-shirts, many of which I was quite tempted to buy including a Nicholas Cage number that I forced myself to walk away from.



Monkey See Monkey Do -- A traditional novelty store with lots of fun gift ideas for friends and family including "Saint Candles," like "Saint Edgar Alan Poe" and the like.


Little Limbo -- Amazing gift store! This one is hidden from the main street and I almost passed right by it but I'm glad I stopped in. It features some really unique souvenirs from Austin and has a great selection of kids items as well.


Prototype Vintage -- I'm still dreaming about this vintage store. This is right next door to Little Limbo so I was very close to passing this one by also but I'm glad I didn't. The shop itself is quite large and features an amazing selection of vintage for men and women.



Lucy in Disguise with Diamonds -- This costume rental store is unlike anything I've ever seen. It is absolutely MASSIVE and has every costume your heart could ever desire. You can rent or even buy any pieces in the store.


Charm School Vintage -- Another great vintage find! This vintage clothing boutique and crystal shop had a beautiful selection of both and super kind staff. I even got photographed in the jumper I bought for their Instagram page!


For lunch we stopped at Cafe No Se which also felt like it could have been a Los Angeles eatery plopped in Austin. At this point in the road trip my body was BEYOND craving some health so I welcomed their avocado toast with open arms. It did not disappoint.





After South Congress we decided to drive to the outdoor shopping destination known as The Domain. Apparently South Congress and The Domain are the two main shopping areas. This upscale outdoor shopping mall did not disappoint. While it was extremely hot and humid, it was nice to walk around, popping in and out of stores, taking advantage of the blasting air conditioning.


While most of the stores were standard to what we have back home, we did stop at The Yard Milkshake Bar, something we definitely don't have at home, to get one of their famous milkshakes. SO worth it. I would recommend splitting one as I'm fairly confident I would have had to be rolled out of that establishement should I have consumed one of those things on my own. It was the perfect afternoon treat though and the perfect end to the day.



Day 4: Goodbye Austin, Hello NOLA!

Before officially leaving Austin behind, we had to stop at an infamous wall art destination just down the street from our Airstream actually and then grab coffee from Alfred at The Line Hotel. Turns out Alfred is located only in Los Angeles, Austin and Tokyo - I can now say I've been to two of the three cities they're located in.



Day four was only about eight hours of driving but based on what I've heard the deep south is like, it was quite obvious where we were driving based purely on the heavy, swampy air. Every time I stepped foot outside the car it felt like someone was breathing hot, wet air down my back. Disgusting.



We made it to NOLA while it was still light out with plenty of time to settle in and explore. Our bellhop recommended Daisy Duke's down the street from our hotel in the French Quarter for dinner. Their tagline is "Nuttin' Fancy just good Southern Food." And boy was it the definition of southern eatin'.


I will say this road trip was not the road trip of my stomach's dreams but unfortunately I wasn't given many options.


After a traditional southern meal at Daisy Duke's - and while it's not my type of food, it was good and the people were super friendly and I would still recommend it - we walked to Cafe Du Monde but not before passing through Bourbon Street. What a sight. That's truly all I can say. It's so dirty and filled with middle-aged (or older) drunk people stumbling from bar to bar or heaven forbid belting karaoke out of some establishment. That's about all the Bourbon Street I needed to see for the rest of my life.


Cafe du Monde saved our evening though with the best beignets money can buy - yes they are as good as everyone claims them to be! I guess that's what happens with a place that's been around over 150 years. They've perfected the art. Word to the wise - 1 order (3 beignets) is perfect for two people. They are not small beignets and you will regret having to eat 3 per person instead of 1.5. In addition, this is an old establishment as I mentioned - cash only! Come prepared.



We definitely needed to get our steps in and walked back to our hotel after that meal and dessert to enjoy our upgrade to a junior sweet, heyooo!


Day 5: NOLA -- Nashville 

While it wasn't the best city to wake up in per say, it was definitely the comfiest bed in that big ole junior suite don't mind if I do.


I'll be the first to admit all the days started blending together especially after Austin as we were essentially driving the same distance every day through very similar terrain.


Nevertheless, we were excited for our second to last destination, Nashville. I would say this was the city I was most anticipating visiting (after Austin of course).



We arrived to Nashville around 4pm and were greeted by the BEST AirBnb by far. We pulled up to what appeared to be a small motel but we were so pleasantly surprised upon entering our home for the next night.



Country music playing on the vintage radio, welcome treats, amenities in the bathroom, the most funky and stylish interior decor, our home away from home in Nashville was absolutely incredible. All the little touches that the host's left behind for us truly made our stay and made us feel right at home. They even had a little pin board with polaroids of everyone who's ever stayed in the room - SO cute!



While the location of the AirBnb wasn't as close to town as I would have liked, we were up for extensive walking after all the hours we'd been spending in the car. We walked about two miles to 12 South  to check out some of the local spots. By the time we got there, it was nearing 7pm and stores were starting to close up shop but we did stumble across a night market that we walked around for a bit.


One thing I learned immediately from walking around is how dog friendly Nashville is! Dogs were everywhere, which only made me miss my little Coco pug at home that much more. I was also pleasantly surprised to see how many boutique fitness studios they had and the sheer amount of people out running. It was nice to see all the young, vibrant energy in the city especially considering most of our drive was filled with the opposite energy going through the South.


We ended the evening with dinner at Milk and Honey which came as a recommendation from a friend and a great recommendation at that. I had an absolutely DELISH salad and was so excited to welcome that health into my life let me tell you. We may or may not have finished the evening with gelato but that's neither here nor there. Calories don't count on vacation remember?!


After dinner we made the walk back to our AirBnb, ready to rest our heads on the last evening of our road trip.


And just like that, our road trip had come to an end. Of course we spent Day 6 in the car driving to Chicago, it easily felt like the longest day in the car at that point but to be expected considering how close we were. But what a blast.



I wouldn't have changed anything other than giving us more time in 3 of the 4 cities but that was kind of the best part of the road trip - it gave us a taste of places to see if we would ever want to go back for an extended period of time. To which I would say yes in a heartbeat (to everywhere but NOLA LOL).


For anyone considering making a road trip of similar distance, my first tip is DO IT. But on the real, I want to offer some of my tips and tricks for making your cross-country adventure a successful one as I think mine was pretty darn successful.


1: Plan your stops (major cities) but not necessarily things you'll do in the city. Leave that up to spontaneity!


2. Pick AirBnbs within walking distance of things to do! After that much time in the car you'll want to stretch your legs.


3. Spring for the extra leg room in your vehicle. It is SO worth it! Just think about the hours upon hours you'll be sitting in the car, wouldn't you want those hours to be comfy?!

4. If you're taking a lot of things - pack the car the night before. Just do it. You'll thank me later.


5. Start the drive early each morning, especially on the days with lots of mileage. It ultimately means you'll arrive to your destination earlier and gives you more time to explore.


6. Stock up on healthy snacks before. Trust me when I say options are limited, Subway is probably the healthiest thing you'll encounter along most road trip journeys, so equip the car with all the healthy munchies you'll need.


7. Pick a good book (or audio book). I would recommend fiction, a story that's going to keep you wanting more. It will help pass the time.


8. Equally as important, find a great podcast! Podcasts have a great way of allowing you to get lost in the material and not even paying attention to the time.


9. Ask your hosts (at AirBnbs) or the front desk (at hotels) for local recommendations when it comes to food. When in Rome...


10. Have a great companion. While I'm sure taking on this kind of drive by yourself could be a very spiritual experience, having great company makes the 3,321 miles seem like a drive down the block...


(Originally Published September 15, 2019)

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