Have you ever been to a place and felt like you had been there your whole life? This is the feeling that Chicago gave me. I immediately felt like I belonged there and was a part of the hustle and bustle. You would think growing up in a semi-small town in the south I would be resistant to big cites in general but quite the opposite, I welcome them with open arms. I was fortunate enough to go with my dad on a business trip there and got to explore the city for three days. So here are my personal experiences from Chi-town and a travel guide in case you plan on going at one point or another! Let’s start with day one which I planned on being my tourist day. I hopped off the place at LAX.. jk wrong song lyrics, but for real I hopped of the plane at Chicago O’Hare International Airport at 8:00 am with a plan and jet lag. This seems like not that early of a time to land but with driving to the Atlanta airport from my hometown, having to be there two hours before my flight left, taking the flight and then landing I hadn’t slept the night before. Knowing I needed to be comfortable and cute I decided to wear a romper with multiple crazy prints from My Closet Etc., a black quilted fanny pack and some brown suede pumps.
Still being sleep deprived I still trekked on to my first spot, the Cloud Gate or as I like to call it The Bean. It is hilarious that I thought there would not be that many people there in the morning because it was packed. Rumor has it to get a picture with The Bean alone you have to get there at 5 or 6 in the morning. Packed or not there it was reflecting the city that loved it so much, round and shiny as can be, The Bean in all it’s glory. You always see monuments like this in pictures and think they’re so wondrous just from the pictures but in person it is an entity of its own.
To get to The Bean you have to walk though Millennium park which is a sight to see itself. As you enter you are welcomed by hundreds of pink and purple flowers with the cityscape as a backdrop which you can see below in some of my pictures.
After The Bean I went to a place called Oz Park that not many people seem to know about. Look out though, lions and tigers and bears, oh my! This place is a park that is Wizard of Oz themed. I thought it was so cute and it seemed to be my dad’s favorite place we went. The locals of Chicago didn’t seem too impressed by it, but I thought it was just darling.
For dinner I had to try some famous Chicago deep dish pizza from Giordano’s and boy was it good. The crust had crust. This is the pizza of all pizzas and I don’t understand why the rest of America doesn’t do pizza like this. After eating all this, how tired I was kicked in and it seemed to signify the end of a day. All of the pictures from day one are below and keep scrolling to read about day two and three!
My Closet Etc./Quilted Fanny Pack/ Suede Pumps
Day two I imagined I was Carrie Bradshaw and exploring the big city all by myself. On this day I knew I was going to go to The Art Institute of Chicago and going to fan girl over all of the famous art I studied in my AP Art History class in high school. Knowing this I wanted to look classy and wore a vintage blue button down pleated dress from The Clothing Wearhouse, and once again my suede brown pumps from DSW (a huge mistake my feet were bleeding by the end of the day).
Ready to be a grown up and navigate the city by myself I called an Uber and had him take me to a coffee shop that had rainbow lattes called The Goddess and the Baker. If you know me you know I am extremely directionally challenged so of course my Uber dropped me off a street over from my destination and it took me twenty minutes and a few circles around the block for me to walk to a coffee shop that was right beside me. Feeling defeated and wondering how I would ever be able to make it in New York where I eventually want to live, I got my rainbow latte and some avocado toast. I now think it was worth it for the gram but at the time I did not.
I was caffeinated and full so I walked over to the Art Institute of Chicago. This place had more famous art work than I could handle. I am not exaggerating when I say I started tearing up looking at some of my favorite works of art, more specifically Van Gogh’s “The Bedroom” and Seurat’s “La Grande Jatte”. I stood and marveled at La Grande Jatte for thirty minutes at least and went back to see it before I left. The impressionist area was by far my favorite area in the museum. It contained paintings and sculptures by Surat, Toulouse Lautrec, Degas, Van Gogh, and a whole room of Monet’s. I really took all of this in unlike most of the people there who looked for two seconds and moved on. It’s impossible to really describe how magnificent all the art work was but I will post some pictures of my favorites below and hope one day you’ll be able to experience them for yourself.
With a bad choice in shoes after four and a half hours I left the museum and sought out food. I went to a ramen bar called The Furious Spoon located in Wicker park and it was the best ramen I’ve ever had. Soon after I realized my phone had four percent and I needed to find an outlet fast so I was able to get a ride home. I looked for the closest coffee shop and low and behold I found a coffee shop that was on my list of places I wanted to go called Stan’s Donut Shop. This was possibly one of the cutest coffee shops I had ever seen, the interior was all baby pink and mint, so straight out of my dreams.
After I charged my phone I explored where I was for a while, little did I know I had found the jackpot of thrift shops, record stores, and old book stores. I now know this area is called Wicker Park and know next time this is one of the first places I’m going to go. Unfortunately it was pretty late and all of the thrift shops had closed or were closing so I only had a chance to go in Buffalo Exchange for fifteen minutes and grab a two piece set with safari animals on it. That was my sign to retire for the night and went back to my hotel.
The Clothing Wearhouse/ Suede Pumps
The last day I did more tourist things I didn’t get to experience the first day. First on the list was The Skydeck. I heard from multiple people that if you don’t get here early the line could be up to four hours long so my dad and I woke up early and got there when they opened and thankfully didn’t have to deal with a line. This was probably my favorite thing I did in Chicago. The view was indescribable. You felt like you owned the city standing on top of all of those buildings. That day I wore a striped red ruched top from Forever 21, some distressed shorts also from Forever 21, a chain belt, red bucket hat, and platformed Fila dad shoes. This is probably my most on trend outfit I wore to Chicago. Ruched shirts, chain belts, bucket hats, and dad tennis shoes are all major trends for the summer right now and will probably continue into the fall.
After the Skydeck I headed to Navy Pier the biggest tourist attraction in Chicago. This pier had a ferris wheel that took you over the city, a carousel, a swing set and other fun things. It really was very picturesque with the water in the background. Here I made sure to take a lot of pictures because of how fun and bright it was. I also did a boat tour of the city while I was here. Normally I think these boat tours are kind of cheesy but this was actually the thing I loved the most about Navy Pier. I got to ride a boat, learn about the cool history of Chicago, and see the skyline from afar. This was the perfect thing to end my day and trip. I hope that you also journeyed along to Chicago with me by reading this post and hope it inspired you to take a trip here!
Similar Striped Ruched Top/Bucket Hat/Similar Distressed Shorts/Chain Belt/Fila Disruptor II Sneaker