Route 66: A Road Trip Down Memory Lane | Part 1: Chicago to Texas

Daley Grace Sweeting

In 2015 I went to America for the first time. I didn't want to go; the US had never appealed to me. I couldn't imagine it having any type of culture. I didn't like burgers or hot dogs. Then there was the whole guns thing. Honestly, the thought of going there scared me a little bit. But my boyfriend had wanted to drive Route 66 since he learned to drive and eventually I was swayed by his enthusiasm.

It would be an understatement to say that I was pleasantly surprised by the experience. Looking back I'm still amazed by how different one state is to the next. And being on the open road like that, in control of your own journey, it changed the way I look at and plan holidays. No more booking 2 weeks at a resort - boring. 

The Route 66 Road Trip set a new standard and so I thought it would be cool to relive it here.


Preparation & Planning

We started by mapping out the route and figuring out how long the drive would be between destinations so we could get an idea of where we should stop. I found a really good travel guide from Lonely Planet that was pocket size and suggested several detours and trip highlights.

After reading a few blogs and tourist sites we decided that two and a half weeks was the best time we could comfortably travel the entire route. I think three full weeks would have been perfect, but I was limited with the amount of leave from work I could take in one go.

We only booked 3 hotels in advance: first city, last city and one motel in the middle of the route that we knew was popular and booked up fast. Everything else we booked a few nights before to give us flexibility. Some people wait to book until the night of their stay. I am not that easy-breezy! I also wanted to avoid being forced to pay high prices because we had no other option.

As we were travelling into the US from the UK, we each had to apply for an ESTA. I also chose to put half of my spending money onto a preloaded card to avoid carrying loads of cash around. I got mine from the Post Office - it was really useful because you can download an app that lets you transfer money from your bank account, perfect for if you get paid while you're abroad. Liam chose to get a credit card that gave you the best exchange rate of the day instead.

Now that we have dispensed with the preamble... Shall we begin?



Chicago, IL

Firstly, I would definitely recommend starting at this end of the route. I'm sure it would be just as beautiful setting off from Santa Monica, but there are two time zones that you cross along the route and it works in your favour to begin on the east coast as you gain an hour each time.

The flight from London took about 7 hours. I don't know if I would go as far as saying that I am scared of flying, probably more accurate to say that I am scared of plunging to my death from 40,000ft and/or blood clots. It's safe to say I stepped off the plane at O'Hare Airport a-okay, albeit a little sore from the groin strain I had given myself doing deep lunges in the plane toilet (I take the prevention of blood clots very seriously.)

We found a shuttle bus that took us from the airport to pick up our rental car and we were off!

Chigaco is a really cool metropolitan city. In a lot of ways, it has a very familiar feel that most big cities have, but it also has a unique vibe. It rained 2 out of 3 days we were there, but there was so much to do, we barely even noticed. We visited the National History and Science museums, and strolled around the local shopping centres and ate lots of yummy food.

Highlight: PIZZA! 

PHOTO: Daley Grace Sweeting

PHOTO: Daley Grace Sweeting

Chicagoan Pizza is a culinary experience I will never forget. In fact, I would go back just to have one more slice! Unlike most pizzas, the cheese goes onto the base first, then tomato sauce in the middle followed by toppings. The base is more like a pie crust than a dough base. In addition to being one of the most delicious things I have ever eaten, it was also ridiculously filling. We ordered a medium between two of us and could only eat a slice each!

We ate at Pizzeria Uno - would definitely recommend.

There are other things I could recommend like Cloud Gate or Lou Mitchell's, which are both great. But one of the best things about Chicago was just walking around and taking in the sights. Even the underground (subway) was entertaining. 

We spent 3 days in Chicago. With good weather, I reckon that's probably enough but I could have stayed one more day. Before setting off, we made sure we found the official Route 66 sign. It turns out, there was more than one so we did rounds and touched them all for good luck.


St. Louis, MO

We only spent one night here so I cannot give you a full rundown of the city or make many recommendations.

My main memory of St. Louis is the accomodation we spent the night in. Liam was really excited to stay in typical American motel, like in the movies. I was terrified! To me, this looked like a place where dodgy dealings were undertaken. I half expected our door to be kicked in by DEA in the middle of the night. Obviously I watch too much television. In actual fact, this is one of the cleanest places we stayed. So, don't judge a book.

PHOTO: Daley Grace Sweeting

PHOTO: Daley Grace Sweeting

The red car is our rental; perfect for adventuring. I would definitely recommend a car with a decent amount of leg room for a trip like this.

Highlight: why did the tortoise cross the road? I don't know but it was so cute to watch! Of all the wild animals I expected to see on our trip, tortoises were not on the list.


Detour: Perry, OK

On our way to Oklahoma City, we slight detour here and went to visit some of Liam's friends in a little town called Perry. With a population of just 5000 people, it was most certainly one of the quietest places I had ever been. It was a bit like stepping into a mid-western Stars Hollow, which I was immediately charmed by. Everyone was really friendly and warm. It was here that I met my now good friend, Beth. Beth taught classes at the YMCA and coordinated football (soccer) summer camps for local kids, which is how she and Liam had met several years before. Liam spent a summer coaching kids' soccer in America in 2009. 

It was also here that I first tried biscuits. No, not McVities, silly! Buttermilk biscuits; served with eggs at breakfast or with chicken and gravy for dinner. They're a bit like a scone but much softer and less sweet. Oh, and AMAZING!

Highlight: seeing a real-life storm cellar!

Everyone had storied that both shocked and fascinated us, of times that they had to climb down into their storm cellars for safety. And how sometimes they had to fish spiders and scorpions out of their first. Scorpions, you guys! I remember turning to Liam in horror and whispering, "Why have you brought me to a place where I could suffer death by scorpion?!" But in reality, we were perfectly safe. I think it was just the initial shock of the realisation that, although America looked very similar to the UK in parts, we were very far from home, Toto.

PHOTO: Daley Grace Sweeting

PHOTO: Daley Grace Sweeting

We stayed with the lovely Spillman Family: Kim & Russell, twin teens Kaya & Cydnee and the lovely Cali. A reunion had been arranged for Liam: a number of kids he had coached when they were younger had come to visit for a Pot Luck dinner. It was really nice to see how happy everyone was to see Liam again.

Perry ended up being one my favourite places of the entire trip because it felt like a really authentic small town, American experience. 

Highlight: 611 Bakehouse. Here I discovered why Americans love sandwiches. They are not the tasteless, soggy, boring kind that we have here in the UK. They came stacked with tasty fillings and on a dozen different types of bread. The kind of place Subway wishes it was. 


After filling our bellies and saying our farewells we were on our way.


Oklahoma City, OK

Like with Perry, we only had one night here and had to make it count. The staff at the motel we were staying at let us know there was a chance of an overnight storm so we decided to get an early dinner in Bricktown and then came back to the hotel to watch the GoT finale - there was no way we were missing that!

Highlight: Chicken Fried Steak! Yes, you heard me: steak, coated in batter, fried like chicken and topped with creamy gravy. In truth, I was disgusted when I first read about it because those ingredients do not seem like they would go well together on paper, but my god, what an invention! If you plan to try this local speciality, I'd recommend the Bricktown Brewery.

Left: Chicken Fried Steak, Right: Turkey Pot Pie

Left: Chicken Fried Steak, Right: Turkey Pot Pie


Amarillo, TX

Our time in the Texas Panhandle was brief. Like, two hours, so I'll keep it brief. 

Highlight: Cadillac Ranch. Think Stonehenge, but with cars.

PHOTO: Daley Grace Sweeting

PHOTO: Daley Grace Sweeting

That's not litter you can see all over the floor; it's cans of spray paint. Visitors are encouraged to leave their mark.

After tagging a caddy, we headed to the Big Texan Steak Ranch. 

To quote Forrest Gump: "And that's all I have to say about that."

Downtown Amarillo

Downtown Amarillo

I’m sure there is much more to Texas than what we had time to see, but in terms of Route 66, we were able to see Amarillo’s best bits in a few hours. Unless you’re planning a Texas detour, I wouldn’t recommend spending the night as there is still so much more of the route to cover.

Here ends the blog post!

Coming Soon: Route 66 recap Part 2: New Mexico to Arizona!