Solo Travel

July 5, 2019 – Chicago, Illinois

My plans were simple, but sturdy: fly into Chicago in the morning, explore the city, then leave on a Greyhound bus for St. Louis the next day. I had some time between finishing my employment with Starbucks and leaving for a month long writing workshop in Ireland. Plane tickets to Chicago were cheap, and I’d never been, so it’d be a nice stop before going to visit my best friend in St. Louis.

I kind of needed to see her. I’d just been broken up with, and in the weeks that followed, I persisted in trying to get him to take me back. I told him that he hadn’t really broken up with me because he did it over text, and that if he wanted to end things he’d have to do it in person. I knew that I’d cry on sight if I saw him in person, but at least that was better than spending my summer alone in my bedroom. So I’d visit my best friend and explore a new city.

Most of my knowledge of Chicago came from pictures of my grandparents’ recent trip to the city, and also Ferris Bueller’s Day Off. The first time I lived in Orlando, one of my roommates was from Chicago. She’d be out of town, though, so I was completely alone in my trip. I wasn’t too worried. I’d walked around Amsterdam and New York alone, and I’d be back in my AirBnb before it got too dark. I wanted to do the typical Chicago touristy things. I’d eat deep dish pizza, see The Bean, and visit the Art Institute of Chicago.

My AirBnb was adorable. I was renting a futon in the living room of this small studio apartment. The whole kitchen fit into a space as big as the bathroom in my childhood home. There were a few plants and books around, and though the host was out at work when I arrived, I felt that if I got to know her, she and I would be friends. She had a sign that said “Don’t talk to me until I’ve had my coffee. And then after that, still don’t talk to me.” There was a french press on the kitchen counter, which was really just a sliver of a normal sized counter. I admired the apartment for a few moments, then got on the L to go downtown.

I navigated my way to The Bean, where I struggled to take a photo with all the tourists in the way. I listened to a podcast as I walked around Millenium Park. It was season two of In the Dark, an investigative podcast about a black man in Mississippi who was on death row despite having been tried six times for the same crime. A few months later, he would be released on bail after over twenty years in jail, but at the time he was still incarcerated so I wasn’t about to take my headphones off for one second. It was a fascinating story to listen to as I took in the sights of the city.

I wandered into what I later realized was a garden dedicated to cancer survivors. I survived losing someone to cancer, so I took the time to look at the flowers and motivational words etched into marble. One said to “Have plans for pleasant things to do and goals to accomplish.” It’s a goal of mine to visit all fifty states, and walking around the city on the warm summer day was certainly pleasant. 

I spent a good amount of time in the museum. It was air conditioned, had free wifi, and I could spend all day there without seeing everything. The painting from Ferris Bueller’s Day Off took up a whole wall, and every time I wandered past that gallery, people stuck close to it like moths to a lamp. 

I took the L to Lou Malnati’s, a pizzeria recommended to me by just about everyone. The pizza sauce was thick, and the taste of it lingered in my mouth as I explored Navy Pier and the Riverwalk. 

I’d walked all over the city and spent not too much money the whole day. I fast walked from the L station back to my AirBnb, because the sun was setting quickly and I wasn’t completely oblivious to what could happen to a small statured woman in Chicago. 

But I really did have an amazing day. If I wasn’t in Chicago, I would’ve been sleeping through the daylight hours in my room in Connecticut to avoid thinking about my ex. I didn’t need him to have a good time, though. I just needed some good food and a lively city, and I could have a pleasant time all on my own.