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Going to Chicago for the First Time? Me too! — A Midwesterner’s Chicago Trip Itinerary for You!

MacKenzie Colgan Student Contributor, Saint Louis University
This article is written by a student writer from the Her Campus at SLU chapter and does not reflect the views of Her Campus.

At the beginning of March, I went to Chicago for the first time. I did not know what to do, but luckily for me, my partner and I knew some people who had been there before. A good place to start is to ask people you know who have been to Chicago before, but if you do not know anyone who has, keep reading to see what others recommended and what I did!

Travel

The most convenient way for me to travel to Chicago was to take the Amtrak. The closest Amtrak station for me was the Gateway Station in St. Louis, and the train ride is a straight shot to Chicago and vice versa, depending on what service and time you get. Not having to worry about a car or having too many bags made the whole trip stress-free, as we were allowed to take one personal bag and two carry-on bags, which is a lot of bags to bring without worrying about packing efficiently. 

If you do not want to take a train, that is OK, because there are many public parking spaces available in Chicago if you want to drive instead. At most, I saw that public parking was $3 an hour or $20 for a full business day, from 9 a.m. to 5 p.m. Some places might be more expensive, but there are so many different lots to choose from.

I am not sure how the flying process works, but if that is what you need to do, please go ahead.

Besides being easy to get to and from Chicago, the city is incredibly walkable. I only had to call a ride a few times, and that was when we had to go to places far away from where we were. Besides those few times, the way we planned our trip made it possible for us to walk everywhere. 

Food

There are many different places to eat in Chicago, almost everywhere you turn. It is impossible to get hungry with so many options, and here are some places I went to.

One place we went was the Original Pancake House on East Bellevue Place. It is a small place, but it was very cozy, and the service was fast and absolutely amazing. I got strawberry crêpes, and the syrup that came with them was fresh, homemade strawberry syrup. Definitely a lot of strawberries, but if you are looking for a breakfast place that has fast service and filling meals, the Original Pancake House is great.

Another place we went to was Giordano’s on West Jackson Boulevard. One thing people told me to do when I asked about food in Chicago was to try deep-dish pizza, since that is what Chicago is known for. We got a 10-inch Margherita deep-dish pizza, and it was amazing. I did not expect to like it because I thought deep dish was just a bunch of sauce, but I was wrong. You should definitely try some deep-dish pizza if you are in Chicago, even if you are unsure of it. You will never know if you like it if you never try it!

We also went to the Little Branch Cafe on South Prairie Avenue for something light since we were having an early dinner that day. I got a grilled cheese panini with fries, which sounds like a lot, but it honestly was not. It was just enough to help me carry through the day before dinner. My partner got food as well, and also got a hot mocha coffee. They said it tasted great, and that the mocha was just right. 

Places and Attractions

If you are like me, then you probably want to get some photos taken while you are in Chicago. A great place to do that is the Color Factory. When you go, there are many different rooms you go through like an adventure, where each room has something different and special about it. There are different activities you can do as well, like trying to guess the flavor of pop rocks to having fun in a ball pit. Most of the rooms have different photo opportunities, too. At the beginning of your experience, you will receive a QR code on a small piece of paper that is linked to your email. With that paper, you can scan it at the cameras set up in the rooms, have your pictures taken and have them sent to your email immediately. My partner and I took many fun photos, and they were all definitely Instagram-worthy.

For a good view of the city, the Skydeck is a great place to go. Before even getting to the top of the Willis Tower, where the Skydeck is located, you get to walk through this beautiful path of Chicago History, from food to famous people who are from there. After the path, you will take an elevator to the 103rd floor of the tower. If you are scared of heights, be prepared. I am also scared of heights, and this was definitely a challenge for me, but the views were so beautiful that it made me forget my fears. Even with my fear, I stepped out onto the glass balcony and took some pictures, because I could never let fear get in the way of a photo opportunity! Besides the views, another great thing about the Skydeck is that it is in the same building as the Color Factory, so you can do two things in one trip.

Another attraction we went to was the Shedd Aquarium. I love aquatic life, and learning more about different species and seeing them up close was so cool. Another awesome demonstration of aquatic life I got to see was the dolphin show. The dolphins performed various tricks while the presenter told us more about dolphins, specifically the Pacific white-sided dolphin, and how climate change affects their environment and their lives. Besides learning about aquatic life from a presenter, almost every tank with living animals had a poster or an iPad you could interact with to learn more about a specific animal. The aquarium itself is right near Lake Michigan. The view from the bay was breathtaking, as you could see the cityscape from the aquarium’s location. 

My Overall Impression on Chicago

This was definitely a great experience! For someone who had never gone before, everything I did above made my experience ten times better. I would totally go back and visit Chicago again, and probably do some of the same stuff I did the last time.

Everyone’s experience is different, so do not expect yours to be exactly the same as mine. I do recommend trying everything that I mentioned above, and I hope they make your Chicago experience as good as mine was. Other than what I recommended, there are so many other things to do in Chicago, so try to do as much as you can to have a great experience!

MacKenzie "Mack" Colgan is a new writer and a freshman at Saint Louis University in Saint Louis Missouri. They double major in political science and music, with plans to minor in psychology. Their hobbies include playing their clarinet and saxophone, making art, listening to Hamilton (or just music in general), read, hang out with friends and family, and more. They hope to build their writing skills while also entertaining others at their time here at Her Campus!