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10 Underrated Things to do in Chicago

Chicago is the third-largest city in the United States, and there are so many things to do here. My partner and I created a Chicago bucket list to complete before we move out of the city. Here are a few of my favorite things that we have done so far that are lesser-known, at least when you are Googling things to do. No shade on the popular tourist attractions in Chicago, they are all super fun and exciting, too! Whatever you end up doing in the city, I'm confident you'll have a good time.



10- Morton Arboretum

Just outside the city, Morton Arboretum has 16 miles of walking trails and is a must-see for anyone who loves the outdoors. I could spend a whole day here and still not see everything. They have a variety of different plants and trees from many different places. The coolest thing about this place is the Human Nature exhibits scattered around the park. These exhibits are giant sculptures designed to prompt people to ask questions about themselves and their relationship to nature. This Is a really neat experience!

9- Chicago Bulls Game

If you’re a sports fan, you cannot pass up on a Chicago Bulls game. We all know that there are tons of sporting events in the area since Chicago is home to the Bears, the Blackhawks, Chicago Fire, Cubs, White Sox, and many more. I am a big fan of basketball, so I may be biased, but I had a lot of fun at the United Center watching the Bulls win. Plus, you can’t miss the famous statue of Michael Jordan. We went on a weekday, so the tickets were not very expensive, but the arena was still filled with fans.


8- WNDR Museum

Everyone always talks about the museums in Chicago. I mean they do boast some of the best in the country after all. As much as I love the other museums I have been to in Chicago, the WNDR is one that I believe is underrated. Pronounced, “Wonder”, this place is an immersive technology museum that allows you to interact with the exhibits. It’s unlike anything I have ever been to before and can entertain you for hours. The exhibits are thought-provoking and encourage you to think deeply.


7- Garfield Conservatory

Garfield Park is widely known as not being the safest area, but that shouldn’t stop you from checking out the conservatory during the day. I spent hours here and could have explored for many more. There are multiple rooms full of unique plants and setups. In the summer, they have outdoor garden areas, while in the winter, they have a colorful, wonderful-smelling placenta room. This is definitely worth the visit, and it’s free!


6- Beach Bars

Obviously, going to the beach in the summertime is one of the most popular things to do because of Lake Michigan. But going to a bar on the beach? That’s even better. My favorite beach bar is located near Navy Pier and is called Nacho Mama’s Beach Bar. There are plenty all over Chicago, but this one is a great place to watch the sunset, enjoy a cold beer, and watch the city lights appear.


5- Concerts

Okay, so going to concerts isn’t really an underrated thing, but Chicago has so many to choose from. Aside from dozens of venues that host all your favorite bands and big-name artists, there are also local musicians. Sofar Sounds is a unique experience where you don’t know where the concert is or who is going to be performing. They reveal the location about 36 hours beforehand, and it’s often a unique place in the neighborhood- like someone’s basement or a chocolate shop. Plus, they have BYOB or other special event nights.

4- Hammocking at Montrose Beach

Whenever I hammock in my neighborhood, people always give me strange looks, as if they’ve never seen anyone hammock before. At Montrose Beach, I always see at least a few other people hammocking in the summertime. Montrose Beach is always buzzing with people having cookouts, swimming, or going for walks. This is a perfect place to hammock and check out Chicago’s beautiful skyline. I always find it difficult to find parking around this area, but it’s worth the walk.

3- BYOB Spray Paint Class

This spray-painting class was so much fun! An instructor taught us the basics of spray painting and let us get our creativity on! There were tons of spray-paint colors to choose from. I went for a She-Ra look, while Alisa took on a Treasure Planet approach. Both of which involve space themes. Of course, we brought a bottle of wine and got a little tipsy while spray painting. There were a lot of cool people there and plenty of photo opportunities.


2- Ping Tom Memorial Park

What was once an old railyard, this park is along the river and has transformed into a beautiful green space. Urban parks are the future of parks because of how sustainable they are. This park is near Chinatown and has one of the best views of Chicago’s famous skyline. On our way home, we stopped to get some Chinese tofu from the famous district.


1- Chicago Magic Lounge

This is by far my favorite thing that I have done in Chicago so far, but I also have been interested in magic since I was a kid. Alisa surprised me by taking me to a show at the Chicago Magic Lounge for our one-year anniversary, and I had a blast. The bar is a speakeasy, so when you first walk in, it looks like you’re in a laundry mat. The bartender was performing magic tricks before the show started, and they have some fun drinks. Not to mention that the dazzling host went to everyone’s table to ask their name and gave them shoutouts throughout the show. And she gave us free champagne to celebrate our anniversary! This was such a wonderful experience, and I would highly encourage you to go to a magic show here.



Let me know if you've done any of these or if you have any other ideas.


Happy exploring!


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