Solo Trip To Chicago: Accidental Adventure After A Canceled Flight

As I mentioned in the prior blog, my LA flight cancelled due to the 2024 outage led me on my first solo trip to Chicago. I had asked on my instagram if I should just take the train to Minneapolis that day or stay in Chicago for a couple days. The people said to say so that’s what I did!

I learned some tips and suggestions in Chicago that I’d like to share.

Housing

This part is kind of wild. So a week before my LA flight cancellation I had already asked my friend from Chicago if she knew of places I could stay at for free or a reduced cost. I was planning on maybe visiting the city for my birthday. Beware I had NO idea I was going to be stuck in LAX airport.

So when I was on the flight headed to Chicago I reached out to my friend again. She contacted her friend and voila. They happened to have a room open because their roommate was away . So I said yes. Yes to rooming with 2 men that I did not know.

I know that this was maybe not the safest decision. Especially as someone on a solo trip to Chicago for the first time. Do I recommend doing what I did? Umm maybe not. But in this case, I trusted my friend and her friends. I also needed free housing for this solo trip to work.

And it eneded up being perfect. Because the roommate came back exactly a day after I left. It’s as if it was meant to be.

Day 1: Being A Tourist

I don’t like being a tourist when I travel. But I activated my true tourist energy. The day before I was so tired from the wahala that I passed out. But the next day I was ready to explore!

First, stop — Downtown Chicago! As someone who has lived in LA, Boston, NYC, Philly, Chicago probably the most phenomenally creative Downtown. There was a river in the middle. Then bridge and big buildings. I was amazed. I was initially in downtown chicago to see a museum exhibit but ran into the famous Bean/Cloud Gate by accident.

Then went to a cute pizza restaurant, Bongiorno’s Cucina Italiana & Pizzeria owned by a local family. That pizza was soo good. Then went to the Chicago Cultural Center where there was a display of really cool Black Art exhibitions. I think they are seasonal so you would have to check the website to see if there are any new exhibits or if the exhibit is still up.

At the end of the day I ended back at where I lived with the 2 strangers — Hyde Park. This is a diverse neighborhood where University of Chicago resides. (Side tangent: the day before I went to the trader joes in Hyde Park and saw the most Black people I have ever seen in a trader joes in my life. I was shook). There was a cute little event outside at the DuSable Black History Museum and Education center celebrating House Music, a music genre originated in Chicago. I recommend checking out the museum website for events going on when you visit. I bought my cute “Black Queen: the most powerful piece in the game” t-shirt and was off to sleep.

Day 2: Living My Black Girl Dreams

One thing I forgot to mention is that when I was on the plane I typed in, “Black people events Chicago”. This landed me on the blkchicago_ instagram page. People were shook that I found so much to do so last minute but it was all due to that page right there.

I happened to be there during Chicago Tech Week which got me in a different part of Chicago where I got to see Common live for free 99!

During the break, I ate the most delicious burger of my life at Krassa Craft in Wicker Park. This neighborhood was a whole Ukranian communtiy with hella antique archived items. If archival heaven was a place THIS would be it. Think vintage, old jackets and CDs. I was amazed and wanted to buy something. But things seemed quite pricey. If you do go, I recommend giving yourself time to buy something.

Ended the night at the “My Best Friend Is Black” comedy show where I got to laugh my night away. Met a random person who is also a local photographer. Sharing this because I feel take taking this solo trip to Chicago made me realize the value of traveling on your own because it opens the doors for you to meet knew people.

Day 3: Last Day

This is when I started getting sad about leaving this phenomenal city. One of my fav hobbies is going to African American museums in different cities. So I had to goto the DuSable Black History Museum and Education Center.

I got hella emotional for some reason. Seeing these stories got me teary eyed. But also inspired me. Then the nerd that I am also went to the Seminary Coop Bookstore. I saw sooo many amazing books. It was like book heaven.

Went to a local community fundraising event and ended it at Elevation Worship concert. which felt special to me because I am from NC and so is Elevation worship. Although I hadn’t listened to them for a while it was special to see a part of my home state in a city I had fallen in love with.

Day 4: Missing My Train

Yep you read that title right. I missed my train by approximately a minute or two. I didn’t know you had to arrive at the Amtrak Train max 5 minutes before. Don’t be like me.

Chicago is BIG y’all. I dont know why I hadn’t realized that. Going from one side to the next can take an hour on the train or even an hour training. Act accordingly.

So then I decided to go to GhanaFest in Southside which is the biggest Ghana fest in the midwest. It was so cool to go to even if it was for a few seconds. Sadly it was cancelled in 2025 due to financial reasons 🙁 but hopefully you can go in a future July date!

Then I rushed back to AMTRAK so I didn’t miss my train again.

Hopefully this gives you some tips of things to do, places to eat at and things to consider when you go to one of the best cities in America