MY Trip to Chicago

MY Trip to Chicago

by Victoria Mongiardo

A few years ago, I traveled to Chicago to enjoy a short four-day trip with one of my best friends. We were young adults at the time, and she had never been out of the state of California. So we decided to take a much-needed break and plan out a short vacation and explore Chicago city. Read on to find out about all the details of our trip and maybe get some ideas for your own trip to Chicago! 



My best friend and I first decided when we wanted to visit Chicago. We knew people hardly ever visited in the wintertime since it is often covered with snow and freezing. As two California girls, we weren’t exactly looking forward to buying snow pants. So, of course, we knew we had to go in the summer. However, Chicago is famously called ‘the windy city’ because of its hot windstorms. My best friend and I were worried about a hot and humid summer week in Chicago, but we booked our flights, selected an Airbnb with a view of the city, and left for Chicago in June. Luckily, when we arrived, it was the best weather of the entire year. It was around 75 degrees F, and there was no humidity or wind whatsoever.  

When we first arrived in Chicago, It was morning time, and we hadn’t had a chance to check in to our Airbnb and drop off our bags. So we carried our small duffle bags with us and went on a brief walk through the famous Millenium Park. The park is located in the Chicago Loop, and it is this huge, green park next to Lake Michigan. I wasn’t used to seeing grass so green since it is so rare to rain in California. We definitely had to stop and take selfies with the Cloud Gate, more commonly known as the bean. 

After doing some research on Instagram and finding the best views in Chicago, my best friend and I decided to head over to the Willis Tower sky deck. The views were breathtakingly stunning. If you love a good city view, this Skydeck was definitely one of the most amazing city views I have seen in The United States. To get a full 360 view of the city, you have to step into a glass room with a clear bottom. My legs were definitely shaking, but you know how it is. You gotta do what you can to get that photo for the ‘gram.   

One of my favorite activities in Chicago was visiting Navy Pier. The pier was lively, with musical performances and fun things to do. We sat on the ferris wheel and enjoyed the views overlooking the lake. The ferris wheel was just slow enough to take in your surroundings and just fast enough to have fun on the ride. We also went on the Sea Dog speed boat tour. The speed boat was much larger than I expected, and the boat was really jumping through the waves. The speed boat ride was the perfect activity for thrill-seekers who love water sports. The speed boat tour was exhilarating and beautiful, and we loved every second of it. With the wind in our hair and the salty, damp air on our faces, we were enjoying our trip to the maximum.   




Since it was both of our first times in Chicago, my best friend and I knew we had to try the iconic Giordano’s deep dish pizza. As soon as you enter the pizzeria, your nose is filled with the most amazing smells of freshly baked pizza dough. We ordered a ‘Meat with more meat’ pizza which was a deep-dish pizza with lots of cheese, pepperoni, sausage, and bacon, and it was smothered with tomato sauce on top. The cheese pull was long and stringy and made the pizza-eating experience all the better!  


If you are looking for a quick snack in Chicago, I could not recommend Garrett’s popcorn enough. Garrett’s popcorn serves freshly popped popcorn with the tastiest flavors. My personal favorite was the Garrett’s mix, a mixture of caramel and cheddar cheese popcorn. 

So, those were the highlights of my trip to Chicago! I hope you were able to get some inspiration for where to go when you book your own trip. Don’t forget to take lots of pictures or even buy travel-based clothing such as this Chicago fleece pullover so that you will never forget your trip. 


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