Daily Chicago Travel Guide | What To Do In The Windy City?!?

Day 1:

Skydeck Chicago

I’ve always wanted to take a trip to the Windy City Chicago. I started to do my research in December of 2019 and my plan was to go for my birthday in January, but I was told that their winter season is quite brutal. While doing further research I discovered that Chicago was having quite a good winter in 2020 so I figured why not book my flight while I had the chance. I booked my stay in Chicago from February 6-9, 2020. The first day of my Chicago trip was so phenomenal. I woke up around 7:00 am to grab breakfast inside my hotel. once I finished breakfast I made my way back up to my room to grab a quick nap. I set my alarm for 10:00 am so I could get dressed, grab a Lyft and head to tour the Skydeck, which gives you the best view of the city. The attraction was about 10-15 minutes away from my hotel and once I arrived the line to get to the top was super long. The employees mentioned that there was an hour wait time, but luckily I had a fast past and I was bumped right to the front of the line.

So, all I had to do was wait on the elevator to head up to the 103rd floor. The fast pass also granted me access to skip the line where you take photos on the glass deck. Once I stepped on the glass and looked down I was super nervous and nauseous all at the same time. My legs began to get weak a little, but I figured I’ve made it this far so I have no choice but to go all the way. It took me about 10 minutes to snag all the perfect shots and great angles. Skydeck was a great experience, especially when it came to me sort of getting over my fear of heights. For the most part, if you want to have time to check out other attractions without wasting time in line go with the fast pass. Having the pass I was in and out in about 20 minutes overall and on to my next destination.

The Field Museum of Natural History

After conquering my fear of heights at the Skydeck I made my way to the next location and don’t worry, this attraction was on the ground. So, I grabbed another Lyft ride and was on my way to the Field Museum of Natural History. Being inside of the Field Museum brought back so many memories when I would go on elementary school field trips to the museum. It was filled with tons of ancient dinosaur fossil and animal sculptures. In addition to this, the part I loved most about the exhibit was the Africa section. There were so many facts about Africa that I was completely unaware of. It gave information on the amount of languages that African’s speak, the culture of Africa and it showed how big the country really is. I spent about an hour in the museum soaking up so much unknown information. I wish I could have had more time to roam around the entire museum, but this is some where that I would for sure visit again during my next trip to Chicago.

Gino’s East Pizza

After exploring Chicago’s Field Museum of Natural History I decided to wind down and grab a bite to eat. I then made my way to Gino’s East to get my first bite of their traditional deep dish pizza. After hearing it was a must try if you’re visiting Chicago I couldn’t leave without getting a slice. Now, I must say Gino’s is quite a unique pizza place. Their establishment has been around for many years and a lot of celebrities have made a stop to Gino’s. Inside the restaurant they allow their guest to leave their mark in the establish, literally. They give you a marker and you can choose anywhere in the restaurant to write a kind note or even leave your signature. The tables, the walls and even the ceilings in you can get up there. I was so surprised at the unique places people found in the restaurant to leave their signature. Now, lets get to the deep dish which I absolutely adored.

I ended up ordering the homemade mozzarella sticks and a small, four slice Gino’s Supreme deep dish. It was filled with pepperoni’s, sausage, mushrooms, onions and green peppers. It takes about 30-45 minutes for them to make the deep dish, but I promise you IT IS WORTH THE WAIT. I started with the mozzarella sticks and when they say homemade they weren’t lying. They honestly tasted as if they were made from scratch. I’ve never had such fresh, handcrafted mozzarella sticks in my life. I wanted to save some room for my deep dish so I ate about three mozzarella sticks and let my guests devour the rest. Next, came the deep dish and my eyes lit up just from the presentation and smell alone. It arrived steaming hot and once I took my first bite. . . cheese was everywhere, which is how I usually love my pizza. Deep dish doesn’t taste like your regular, everyday pizza. It’s 1000x better, especially at Gino’s! After I finished my meal I decided to head back to my hotel to get some rest due to the jet lag from the late night time arrival the day before. I did this so I could be fully energized and have time to explore the city on day 2.


Watch My Chicago Travel Vlog Here!!!

A few places in this post were sponsored, but as always all opinions are my own. Thank you to Skydeck, Field Museum and Gino’s East for having me.


  1. Taylor says:

    I love my city, I haven’t been back in years. I’m glad you enjoyed yourself and there is so much to do in the city.

  2. Megan says:

    Did you get to go to Portillo’s or Giordano’s? Those are chicago originals.

    1. Desiree' says:

      I enjoy your blog. I learned about it on Black Travel movement.
      I love to travel! You have given me ideas/suggestions for my next trips. Thanks for sharing.

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