I’m really only super interested in the Willis Tower!
~ @Courtneyyy
To experience chicago to the fullest, I would suggest doing a lot of the less done activities instead because there are a lot of cool things to discover. Since I live close to chicago and go there regularly here are some places that I suggest you go to:
To start off your morning, go to a breakfast place called Wildberry Pancakes and Cafe during one of your visits in Chicago. The place has everything from nutella pancakes to a mexican style eggs benedict for dining and smoothies and other beverages to top it off. I’ll warn you though, the place is extremely busy and I suggest you come early in the morning. If you don’t have a reservation it’ll probably take you a solid 20 minutes to get seated. That isn’t much of a bother though, considering that the restaurant has a beautiful outline of the city and Millennium park right next to it. The food is outstanding, and it’s not worth missing. Take my word for it and go check it out on one of your days here.

The best part about being in the city is waking up early to see the city come to life. Going on the river walk in the early morning is a great way to go on a stroll and see some cool buildings as your passing through. This will lead you soon to the Merchandise Market, which is kind of fun to see. It’s a huge warehouse filled with a bunch of kitchens and other luxurious rooms that no one can afford, but it’s an interesting experience.
If you’re looking for a bite of some sorts I highly recommend going to the French Market below the Ogilvie Train Station. A lot of the vendors are expensive but the food ranges from a lot of variety. There’s good Bubble Tea, BBQ, vegan food, Italian food, Mexican food, etc that you can find. It’s closed on Sundays which you’ll have to watch out for but the whole market has a nice aesthetic and some food that has been checked out by food network stars.
Some gems of chicago are our museums and other public areas, like the Art Institute, Shed Aquarium, Field Museum, and the Museum of Science and Industry. These places will be somewhat pricey which is expected of most museums and anything really in Chicago but the experience is worth it. Personally, it comes close for me between the Field Museum and the Art Institute but all are great places. The Art Institute has great exhibits of ranging art and the Field Museum is bursting with history. One time on a fourth grade field trip we went there and I got lost and it took them 3 hours to find me. The place is huge and very interesting for anyone who loves history.
Last thing I wanted to mention are the Italian and Jewish neighborhoods. A lot of the districts that encompass a wide spread of cultures are dissolving these days which is a shame since you can get a feel as to how life is like for some of the people that live in or near Chicago. Some of the neighborhoods that are still closely knit are the Italian and Jewish neighborhoods. You can find good restaurants that don’t get enough attention and see other areas of the neighborhoods. In my opinion, Chicago is cooler the deeper you dive into it and stray away from the busy center.
That’s all I wanted to say but if you have any questions I’d be happy to answer them if you DM me. I don’t want to make this a longer essay than this already is lol but if you need anymore tips or suggestions I got tons of them.
Good luck! Guess that still doesn’t answer your original question though ahaha.