6 Things To Do In Chicago

6 things to do in Chicago

There is something about Chicago that I loved. The historical landmarks only enforced my vision on Chicago. Walking through the Chicago subways brought me back to watching biographical movies of African American musicians in the Jazz Era. Chicago was the place where Michael Jordan really made a name for himself and my fairy godmother Oprah prospered as the greatest philanthropist in America. Not to say that Chi-town isn’t what it used to be but these landmarks was something I truly loved and admired about this destination. The first annual Women in Travel Summit was the excuse I used to see this beautiful city. I hoped on a greyhound from Downtown Toronto, taking 10 hours which felt longer than New York for some odd reason. The Women in Travel Summit gathered female bloggers globally to network and learn about ways in which we could all be successful in the world of travel. The event took up a lot of wonderful time, so everything on my bucket was most definitely not fulfilled. However, being the travelista that I am; I managed to fit in many different activities and here are the 6 things I did:

  1. Deep dish pizza

Prior coming to Chicago, a girlfriend of mine who attends Law school 45 minutes away from the windy city, let me know if I’m in town it is a must to get a deep dish Chicago style pizza. She mentioned Giordano’s pizza as the best place to grab a bite. When I met up with my home girl who lives out there, she told me that it was a chain restaurant and knowing the individual that I am, I may not be fully excited. Either way, I tried it out and I am glad my friend knows me well because I felt it was bit mediocre. Not say to the deep dish was not good, it was delicious. However, the next time I’m in town, I am heading to a local known spot where the deep dish is fresh.


2. John Hancock building

While attending the conference, I was staying with someone and was so busy networking with awesome female bloggers, I wanted to make it necessary to hang out with that individual. Her name was Lesley and was such a great host, so much that she took me to see the John Hancock building. It was a walk-able distance from her place but we decided to grab a ride through UBER to get there quickly as it was extremely cold that particular weekend. Once getting to the Hancock building there was wait time of 20 minutes just to get up to the top floor and view the site. When we got there, we didn’t want to pay the astronomical drink prices just to see the view, so we went to the girls’ bathroom where we got a nice view of downtown Chicago and snapped a few photos. The view from the John Hancock building is beautiful and would recommend everyone to check it out. If you’re female identified, go to the bathroom and get the best view of the city on a great budget: FREE.That’s Leslie


 3. The Weiner’s Circle

Now, I had not heard about the Weiner’s Circle until Lesley’s good friend who was in town from L.A. told me. Apparently, this place is a big deal that people all over the world come to check out. Basically, they curse at you while you are making your order. While waiting they may curse you even more. It is of predominately black women who serve you. I will give it to them for being quick with their words and strong with their presence. I thought it was pretty weird but once the one girl in the back cursed me and my so called “nappy headed self” it was fun in spirit. Customers come in and say the most derogatory things while getting the famous Chicago style hot dog. The food was greasy and mediocre for myself but I recommend to everyone, old and young to come check out this spot late at night when you have exhausted your night on the town.Chicago style hot dogs.


4. Harpo’s Studio

As a black female traveler, I always told myself if I was ever in Chicago I got to go to the Oprah Winfrey Show to see my role model do what she does best. Her show came to an end a few years back and that did not stop me from the opportunity to check out her production facilities, Harpo Studios. A fellow attendee of the Women in Travel Summit, Chelle from Brown Girls fly was so kind enough to take me to see Harpo Studios. Great place to get your Instagram pictures and let people know, you know where Oprah chills. Secondly, it was such a inspiring landmark to reflect on how far she came in her life from a girl who was born into poverty to one’s of the richest women in America. I would recommend going to see Harpo Studios.


5. Obama’s Home

Now, word on the street is Obama’s main home is in Chicago. Hearing this I knew I had to see the beautiful neighborhood called Hyde Park. Its walking distance to the University of Chicago which I thought was pretty cool. I will stress caution that you will not be able to walk up to his place for the reason being an entourage of secret services around the area. Chelle from Brown Girls Fly made a strategic approach in taking the back route in order to come up front near his home and not look like a loiterers. Overall, even if you can’t check out Obama’s home, the neighborhood itself is super beautiful with huge Victorian houses . It has great restaurants, art galleries and the best African American museum.President Obama’s home. 


6. The Shrine

In Chicago, I envision an era, where music was good, the women were semi-liberated and it was critical for musicians to come to the windy city and prove to the local crowd that they are a star. This audience was primarily African Americans who migrated from the south and who used music as an escape from reality. Chicago was what New York is today to most people, the music and theater capital. It was where Common was born and the birth of Neo-Soul music emerged from. Therefore, I attended a Elle Varner concert at the infamously Shrine music venue. Here is my a little clip of Elle Varner performing.


There is so much rich history, that the days I was there were not enough time to celebrate the accomplishments of the city. Don’t worry I will make a goal to be in Chicago very soon and explore a bit more of what it has to offer.

Walking through the Chicago subways brought me back to watching biographical movies of African American musicians in the Jazz Era. Whistling at a beautiful women, while combing back the fresh perm that he just got done. Jazz music following their every move in the hopes of scoring a hit and getting out of the realities of systemic tensions. I know you’re probably thinking to yourself, what an imagination I have. However, this is the feeling that Chicago gave and I hope you can relate or one day see what I am talking about.Here is a video illustrating my Chicago trip. Enjoy!

Published by JessieO

My name is Jessica Opoku, and I’m an experienced lifestyle travel specialist with a deep passion for adventure. My background, experience, and unique blend of skills enable me to easily understand the travel personality of others and help them pick the perfect itinerary and excursions whenever they need an adventure.

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