Top Ten Things you MUST do in Chicago


This weekend my family and a took a quick trip to Chicago with our cousins from South Carolina. They had never been to the Windy City before so we made sure to do all of the touristy sort of things. We wanted to ensure they got the full Chicago experience, as this is a trip my family takes often! We did some things I’ve done before, and some I had not yet experienced, which overall inspired me to share with y’all ten things that I think are worth seeing and doing when in Chi-Town. Some of these are hidden gems while others are Chicago classics, but I hope this inspires some fun things to do on your next trip!

1. Wrigleyville


This was one of the first stops we made when we got to Chicago and it was so fun! There are lots of neat places to eat and tons of shops with alllllll of the Cubs gear. Even in the winter when there’s not much going on it’s still such a cute part of town and exciting to imagine all the fun that occurs during game time in the summer.

2. Skydeck Ledge at Willis Tower

The Willis Tower (formerly Sears Tower) is home to an attraction I’ve been wanting to try for so long! I’ve never been very afraid of heights but I’m not going to lie I was a little bit nervous for this.. At 103 floors and 1,353 feet high the glass ledge sticks out from the building and allows tourists to step out onto it and seemingly feel as it they are standing on air. Once I was up there, it wasn’t as scary as I had anticipated but was honestly just SO cool. It’s definitely a bit of a thrill and something I’ll always remember doing.

3. Hamilton

The reason we all came to Chicago on this trip was to go see Hamilton, and WOW did it surpass all expectations. I’m not sure what exactly I was expecting as I had only listened to a couple songs, but this was truly unlike any other show I’ve ever seen. It was brilliantly written and the actors and actresses did an amazing job with the way they danced and interacted together on stage. My sister has been itching to see this show since it came out on Broadway and to watch how happy she was to be here made my night. It was definitely worth the pricier tickets and was seriously unreal. I want to see it again!

4. The Hampton Social

Directly following the show, we headed to a late dinner at The Hampton Social and it was truly the cutest place ever. The entire restaurant is decorated very aesthetically and even has a fun wall with a light up sign that says “Rose all day”. Not only was the ambiance and decor incredible, but the food was absolutely delicious! My mom was raving about their brussel sprouts and I devoured my shrimp tacos. Such a fun ending to such a great day.

5. The Bean at Millennium Park

While this is kind of something basic and typical to do in Chicago, it’s still a must-see! I’ve been here so many times and it’s still super fun to take pictures in front of, there are so many ways to get creative with the reflection. Definitely a staple when visiting Chi-town, you don’t want to miss this, especially if you’re visiting for the first time!

6. Stan’s Donuts

We had never been here before and randomly just decided to pop in as we were walking from our hotel towards Michigan Ave. and to my surprise, THEY HAD GLUTEN FREE DONUTS! (Olivia Kegley— I immediately thought of you and how much you would love this). I got a blueberry donut and was truly in heaven. They didn't even taste like typical gluten free replacements would. Regardless of if you’re gluten free or not they had so many different kinds of donuts to pick from and the inside of the shop is decorated so cute!

7. High Tea at The Drake Hotel

Annie Kate had the suggestion to go get tea in the afternoon at The Drake. She had heard about how famous people such as Princess Diana had High Tea here and she suggested we go see what it was all about! We had such a wonderful afternoon and felt so fancy, sipping our tea and eating things like mini sandwiches, scones, and cookies. It’s a pricey thing to do but was definitely a fun thing to check off of the list to say we’ve done it!

8. Eataly


With my family being Italian, this is a place we discovered a couple years back when in town with my grandma. It’s a hugeeee two story building full of about everything Italian you could imagine, from breads to wine, cheese and gelato. You can sit and eat a meal, order fresh meats and cheeses, and really get anything you could possibly want! We had a blast looking through all these yummy foods. This is definitely a must-do if you’re a foodie like me!

9. Shopping on Michigan Avenue

One of my most favorite things to do in Chicago is walk down Michigan Avenue and shop!!! We mostly window shop but there are definitely some stores we always pop in, such as the big Forever 21 and Tiffany’s! Lucy picked out her first piece of Tiffany jewelry this trip and it was so cute to see her get so excited about it. While walking down Michigan Avenue be sure to stop in Water Tower Place and the Bloomingdales mall.

10. Giordano’s Pizza

A Chicago Classic, Giordano’s is some of the best deep dish pizza you can find in the city. We come here almost every time we are in town as it is truly one of the best foods ever. It was so fun to be able to share this with our cousins when they visited for the first time!

I made a Youtube video with some highlights of our trip linked below. We truly had such a great time and made memories we will cherish forever!!! Be sure to check out all of these fun things to do the next time you’re visiting Chicago!