Seizing the opportunity… Part 2

This the second post in a three-part series. My trip took place June 18-21, 2022.

So much anticipation, and now it’s here! My trip to Chicago for Father’s Day and Juneteenth weekend, and it couldn’t come soon enough.

Flying into O’Hare International Airport is an experience… one which many Southsiders choose to forgo if they can fly in and out of Midway. In this case, the price was right, the departure from Austin was good, and it offered a unique opportunity to start my adventure. My plan was to take my time getting to the Airbnb house to meet up with the family, to see some of the city via public transit, and ease into the trip. While many would avoid public transit at all costs, I eagerly awaited my chance to live like a native again.

Once my plane landed and arrived at a gate, I found my way out of the airport and onto a Blue Line train. Let the walk down memory lane begin, or The This Was Your Life tour, as I jokingly called it.

Photo by Albany Capture/

My grandparents lived on Montrose and Kedzie when I grew up, and the Blue Line passes the Montrose exit on the Kennedy Expressway. Along the way, messages started pouring in from the family and they were in awe of my choice to take many modes of transit rather than an Uber ride to the house. I enjoyed the sunshine and the beauty of the Northside – memories of visiting my grandparents, concerts and comedy shows Husband and I enjoyed, the wooden porches, window box gardens, travelers and natives just going about their day. Thank God for sunglasses while I let a stream of feelings come and go.

Before I knew it, the Blue Line train arrived at the Thompson Center, which made for an easy transfer to the Orange Line. As rode the trains, all the news stories of crime and chaos on public transit and in Chicago came to mind. I saw none of the on this ride nor on the trip, not to say that it didn’t happen elsewhere on the trains or in the city. I was really enjoying this beautiful day, and I hoped many others were too. I took in the view of downtown as the Orange made its way south and west, all the way to Midway Airport – the one I didn’t fly to.

I soaked in the city as the train rolled on, and I thought about the countless times spent downtown and about all the great memories throughout my life. Always something new and exciting to see or do, good food to eat, and way too many choices… Art, music, the lakefront, sports, shopping, architecture, freedom, and escape. I know what Chicago has become in many ways, but I know what it still is and what it can be – corrupt, violent, nasty, the worst of the worst and yet, good, kind, hard-working, full of opportunity, beautiful, and the best of the best. There is nothing like it, hands down.

My ride on the Orange Line took me through many areas from my past life (before Texas), including past McKinley Park, one of my favorite places in the city. Lots of areas looked the same, save for a new Dunkin Donuts or other small changes, but I saw new construction many places, too – it almost looked like areas that needed opportunity were thriving. I hoped so. Stops at 35th St/Archer, Western, Kedzie, and Pulaski all reminded me of different times in my life and people nearby. Friends from high school, old co-workers, things that made me the hardy person that I am. As I neared Midway, I called Weber’s Bakery to see if cakes on display were still available – yes, they were. I excitedly hopped on the Westbound Archer bus, and I reminisced about late nights drinking, playing board games, and eating Villa Rosa Pizza with old friends… I loved seeing familiar businesses and news one I wouldn’t have time to try, at least not on this trip.

A Weber’s Cake to help us celebrate, and a clean slate to start fresh.
Photo by Chrell

I thanked God for the nice weather for my travels and was grateful the heat wouldn’t melt my Weber’s cake – whipped cream with strawberry filling – while I waited for my Uber to complete the final leg of my commute to the Airbnb house, mere blocks from my family home in Mt. Greenwood. I mentally prepared myself for the occasion – I would finally get to meet my nephew and reunite with my family, though unfortunately Husband was able to join us. I was excited and grateful, though I also reminded myself that people are complicated at times, and I can only control myself. All I could do was try to best the best version of myself and, while I was optimistic others would do the same, I would not put unrealistic expectations on this experience.

I will soon write a Part 3 to complete my story, but I will tell you that I am glad I took the trip. There are many moments that will stick with me forever, including the first time I held my nephew and made faces with him. No matter what apprehensions we all came in with, we hugged, laughed, and acted like a family – a rare and unexplainable feeling of love and belonging that I don’t know when I last experienced with them.