Chicago in my opinion is one of the greatest cities in the U.S. I went for the first time about ten years ago with my mom and grandmother. I was still living out East at the time so it was technically my first time in the Midwest. I remember my mom swearing that she would never live somewhere so cold (writing this post from my room in Minnesota). It was then that I saw how cool this city is. Chicago feels like a cleaner version of New York City. There are endless things to do and after visiting a few times over the years and twice this summer I felt that I should write about some of my favorite things to do there.


Chicago does an amazing job bringing greenery into urban spaces. There are tons of parks, both large and small scattered around the city. What I love about them is they are very modern with various types of sculptures. Some of my favorite spots are Millennium Park (where the famous Bean is), Grant Park (many events here like Lollapalooza and Taste of Chicago) and Jane Addams Memorial Park.

Architecture Tour

I finally did the boat tour that explores some of Chicago’s coolest architecture. For $35 you can learn all about the tall buildings that line the river. If you’re someone that doesn’t like to pay attention to people talking for a long period of time, it’s still nice to cruise around . ⅘ of the people I was traveling with enjoyed this while one fell asleep on the floor 15 minutes in. I guess 15 year old boys don’t enjoy being lectured about buildings.

John Hancock Observatory

For $25 you can go up to one of the top floors of the John Hancock Building and see an outstanding view of Chicago and Lake Michigan. Though I would typically not pay to do something like this, I would say it’s worth it. If you don’t wanna pay, a good alternative would be to find a tall hotel/building and try to get to the top floor even though you wouldn’t get the 360 degree view.

For another $25 you can dine at the very top of the skyscraper. I didn’t do it this summer, but during past trips I’ve had their delicious brunch buffet.

The Beach

The beach in Chicago is a happening place during the summer. There are tons of people playing volleyball, running, swimming and chilling out along the shore of extremely large Lake Michigan. It’s a great free activity that lets you take a break from the bustling city. We spent hours here and never got bored.


Chicago currently has a production of Hamilton playing at The Private Bank Theater. The musical was amazing and though I thought it was originally overhyped, I can now say that it is not. Both my friend and I that went get made fun of for be pretty emotionless (they just don’t understand us Katherine) and we were both tearing up in the end. If you are in Chicago, I can’t recommend getting tickets more.

Favorite food spots:

Rosebud– Italian restaurant that I would honestly go to Chicago for.

Ghirardelli- Chocolate and ice cream (need I say more?)

Gino’s- I 150% would rather eat thin crust but Gino’s deep dish is worth a visit.

The Halal Guys- Cheap Middle Eastern food that originated in New York (get extra white sauce)

MingHin Cuisine- Dim Sum located in Chicago’s Chinatown. Amazing food, great prices and beautiful interior.

And you’ve obviously gotta belt this at some point.



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