Welcome back, friends! I’m super excited to share with y’all my Chicago experience! I honestly fell in love with the city in the two days I spent there and I’m already ready to go back!
For the last year and a half, I have been working towards a Master’s degree through the University of Saint Francis in Fort Wayne, Indiana. I was doing it 100% online and knew that because I had never physically visited my school or developed any real connection to it that I wanted to go and walk at my graduation. Both my mom and my boyfriend agreed to come with me to celebrate. Yay me!
When I started looking into prices, I noticed that flying to Fort Wayne was pretty expensive. So I looked at nearby cities that would be less expensive. That’s where Chicago comes in. A major city and airport hub, it’s fairly inexpensive to get from New Jersey/ Philadelphia to Chicago. I had also never been to the Windy City so the possibility of exploring a new place was obviously enticing. We all agreed on Chicago as our weekend spot and I immediately got to work on booking.
We stayed at the Palmer House, a Hilton Hotel, right in the heart of downtown Chicago. The Palmer House is the oldest operating hotel in the country dating back to 1871. Our rooms were quite small but the rest of the hotel made up for it. The lobby is stunning and hosts the second most photographed ceiling in the world…well maybe the 1st ever since that whole Sistine Chapel no photo deal with the restoration company.
Our first stop on our Chicago tour was food…duh! We got in pretty late at night and decided to start fresh with a new day. I had discovered a list of best breakfast spots in the city and picked the best looking one from the list: Wildberry Pancakes & Café. Touted as having larger than life “American” sized portions, I was instantly intrigued. And I’ve got to say, those were the best pancakes I have ever had. I ordered the cinnamon roll pancakes, which were drenched in cinnamon sugary goodness. I’ve had dreams about these pancakes. You need to try them.
But be prepared to wait. On a busy day, the wait time can go up to 2 hours. We put in our phone number and spent the time exploring Grant Park next door. A great way to pass time and explore some of Chicago’s famous spots!
After breakfast, we hopped on the bus (Chicago’s public transportation system is phenomenal by the way; take notes, NYC) and made our way over to Navy Pier. Full disclosure: Navy Pier is incredibly touristy. Overpriced food, museums, and gift shops reside in this spot. That being said, it’s a great spot to take beautiful pictures of the Chicago skyline. They also have an open carry law on the pier so you can purchase an adult beverage and walk around which is awesome on a gorgeous spring day.
Seeing that it was Cinco de Mayo and I’m a good American who celebrates culturally inaccurate “holidays,” I made a reservation for the Broken English Taco Pub for an early dinner. It’s a super cool restaurant that the 86 year old Grandma that lives inside of my body would describe as “young” and “hip.” I will say that while the food was good, the drinks were on the small side for how much they cost. I’d stick to bottled beer here if you are looking for bang for your buck. And definitely make a reservation; this place is popular!
Next up on our Chicago tour was the famous Willis Tower, formerly known (and truthfully still known) as Sears Tower. Completed in 1973, Sears Tower was the tallest building in the world for almost 25 years. Today, it is the 2nd tallest building in the United States and the 16th tallest building in the world. The cool feature of the Skydeck is the three clear glass boxes that sit three feet out of the window that allow you to stand and look all the way down to the ground. This is definitely the thing that everyone comes to the Skydeck for. You can move easily around the main floor area but the Skydeck boxes have a queue. This is actually really smart because it allows everyone to experience the boxes equally. Pro tip: you only get 60 seconds in the box to take all your pictures so plan them out while you’re waiting in line. This maximizes your time and gives you a chance to actually enjoy the experience instead of just focusing on the pictures!
The last stop on our packed day was a ghost tour. Now, if you’ve been reading my blog long enough, or know me at all, you know I love ghost tours. I try and do them in every city I’m in. So far I’ve checked off Boston, Philadelphia, Charleston, Edinburgh, and Washington D.C. The cool thing about this ghost tour was it was the Ghosts and Gangsters tour. For about 3 hours, we walked around downtown Chicago learning about the history of Al Capone and some of the major historical events that have produced some very interesting ghost stories throughout Chicago. My mom may or may not have even seen a ghost…if you believe in that kind of stuff.
The next morning, we made our way over to Stan’s Donuts, a staple in the Chicago breakfast scene. These donuts are huge and delicious. As a big donut fan, I highly suggest you check them out. We then made our way over to the boating docks for an architectural boat tour. Chicago is home to a famous skyline with even more famous buildings. And it’s growing at a rapid rate. We spent the next 1 ½ hour learning about the different types of architecture and how building architects create such magnificent buildings. Architects take into account not only how the building will be structured but many buildings have little “nods” to their neighbor buildings. Some skyscrapers have been created with certain kinds of reflective windows so that the building changes and grows with the city. I highly recommend taking one of these tours. They’re a great way to learn about the city’s history and see some spots you would miss otherwise!
In the middle of our architecture tour, the temperature rapidly dropped out of nowhere. It went from 72 and sunny to 43 with imminent rain. By the end of the tour, all of us were freezing and shivering. But we were about to get the best view of the whole tour. That’s when our tour guide said over the loudspeaker, “Get up and take the picture. When you look at it 3 years from now you won’t see how cold you were.” Boy, did this get my cold ass up out of my seat. Because she was right. I don’t look at this picture and see how cold I was. I just see the gorgeous skyline. And this is a lesson for everyone, and even myself sometimes, on how to travel. Don’t hold back from anything because of temporary discomfort. Don’t sleep in, don’t ignore opportunities, and don’t take your time for granted.
After one last stop to eat lunch at Nando’s (because…well…obviously) and our quick stop in Chicago had come to an end. I definitely fell in love with Chicago a little bit during our short stay and plan to be back very soon. What are your favorite Chicago spots?