Days Spent Staring At Waves: Reflections on Chicago

People from Chicago talk country as hell. I’m a Southerner myself, born in South Carolina and raised between there and Baltimore, and the accents take me back to the deep south roasting pigs on the pit and running around in my grandma’s backyard. But Chicago’s Southern roots, stemming from the Great Migration of the early 20th century, is probably my fourth or fifth reason I love it so much.  I’ve enjoyed a month and a half of living in Chicago in South Shore, substitute teaching and doing my remote job on the side when needed. In a few hours, I’ll be on the Metra train to the orange CTA line to Midway flying back to Baltimore. But for now, I’m doing what I always like to do when I’m in Chicago - sit and look at the waves on the lakefront.

July 2015 is where my obsession with Chicago began. It was a hot day, and my brothers and I were chilling at the Lakefront at one of the beaches downtown. I took a picture on my Windows phone - a Lumia 1520 - and remarked how the picture could’ve been taken in Miami or Los Angeles if Santa Monica was a proper city. This urban metropolis that was so beautiful and well designed and had this lovely beach and had a cost of living similar to my own city of Baltimore.

But I remember even before then during my first visit - either 2013 or 2014 - to meet my paternal grandfather  in the suburbs for the first time  - how magical the city felt. It was night time and we were making a quick visit from Milwaukee. This visit was also the first time I had White Castle. I was not impressed with the burger nor fully understanding the concept of a slider.  It would take me a couple of years, but by 2021 I was buying the frozen 6 packs from Safeway biweekly. We then went by this huge McDonalds and rode through the lakefront not really stopping in the city but cruising through. I didn’t see Cloud Gate until 2015.

This time around, I wanted to stay long enough to really integrate myself in the city and see if I could brave a Chicago winter. While I’ve been here, I’ve spent a lot of time writing, organizing Cousin Tito things for my return home, and listening to the traffic of South Shore. But I’ve been outside too - going to Cole’s Bar for an open mic, connecting with artists at different events across town, and just experiencing Chicago as I would if I was making a permanent move. I’ve gone to the Promontory to see Manywellz who is so talented, but also Grown Folks Stories which is hilarious.

But now the time has wrapped. From where I am I can hear the waves crash against the shore and see them. There’s been days where the wind creates large violent waves and there’s been days where the lake feels still and eerie. There’s been days when the lake is beautiful and bright blue and then there’s been days when the lake has been grey. Today is a grey day and it’s also very foggy so I also can’t see where the lake ends and the sky begins. Nonetheless, today is calm and I feel so encouraged to write and reflect and just be so grateful that life has oriented itself this way for this opportunity to come.

Chicago is a mixture of every city that I love - Baltimore, Washington, DC, and New York. The Field Museum and the Museum of Science and Industry have these rich federal style designs surrounded by these lush green grass landscapes that’s very District of Columbia. There was a time I actually found myself missing DC, so I walked to the Museum of Science and Industry and just sat on the bench outside pretending I was at one of the Smithsonians. Perception is reality, right?

When I walk through the more Black parts of Chicago, I feel like I’m in Crown Heights, Flatbush, or Midwood. There is a rich diversity here in the city, and even though these areas aren’t quite setup like Brooklyn, you can still feel it in the people. I’ve walked from Midwood to Downtown Brooklyn before, coming from an interview for a substitute teaching position at a high school there, and walking the stretch of Brooklyn feels very similar to the walks I’ve had in Chicago from South Shore to Kenwood via Cottage Grove and some side streets.

And then home - Baltimore. Baltimore would’ve been like in a universe where our metro was properly funded and built and our density was appropriate. I guess the charm of Smalltimore is its scale, but I personally feel this has moreso damaged the city than helped it. There’s power in density, something Councilperson Ryan Dorsey is looking to highlight, and urban design and the built environment. I say that to say the 2-flat and 3-flat is one of the most sustainable home designs. I am inspired by the stories of immigrants coming and using the 2-flat structure to support their family and offset the expenses through the other unit. Land-use wise, it makes the most sense as something that’s not scary and daunting like a mega tower while being more efficient than a single-family townhome. Perhaps slightly larger lot sizes and a different approach to living could’ve saved many during the housing crisis?

Chicago is the city where the two rappers who I grew up listening to hip hop were born and bred. I’ve explained it before, but Kanye and Lupe were my introduction to hip hop through my older cousin who would always play their music aloud. Even though my aunt played Jay-Z and house music all the time, that didn’t really grab me like my cousin’s music did. I remember begging to listen to “College Dropout" and “The Cool” on his iPod, and was so vindicated when I finally got my own. I saw Lupe Fiasco live for the first time at Howard Theatre a month before I moved. He’ll be teaching Rap at JHU this year. I hope God allows us to cross paths and will work in a way that will allow us to do so.

I first tried to move to Chicago from California in 2019 hoping to transfer there with Apple instead of Baltimore. Back then, studios in Rogers Park were $900. I was geeked, considering my studio in Baltimore downtown was going to be raised to $800. I’d have preferred Rogers Park. That didn’t work. I tried again in 2021. Studios were still $900. That too didn’t work, but that failure and the desperation to not be at Towson did bring me to New York City, something I am eternally grateful for. I thought after moving to New York I would be satiated of my urban metropolis living fantasies. I told myself then that I wouldn’t have to move to Chicago, that nothing would compare to Harlem or Brooklyn. That I had seen enough. And the Harlem and Brooklyn rents said nigga please as my job said Tito you’re not moving up in this company so please get a lollipop and get comfortable. And last year I quit and moved. A studio in Rogers Park is now $1100, but I like South Shore and would probably choose to stay on this side of town if I moved back. But, now I’m looking on Zillow for 2-flats, figuring how much I need to save for 2027 thinking if I should consider a cash-out refi on my current home. I look forward to the day I can walk downstairs and in fifteen minutes be at the shore watching the waves lap over each other with the skyline in the distance.