To select the most beautiful and quintessential American city is a difficult task. For me, it is a battle between New York, Chicago, Los Angeles, New Orleans, and San Francisco. They each represent so much about America and so many actual Americans. They each possess storied histories and are still major players in the American story today. It’s a tough choice but for me, it’s Chicago. People say you never forget your first love and Chicago was mine.
I fell in love with the Windy City when I was 13 years old. It was one of the first times I was away from my Mom for more than a night. On this trip, I was traveling with several of my friends from the Boys and Girls Club to attend a youth convention. I filled my Mom’s large, seemingly bulletproof, 1970’s grayish green Samsonite suitcase with some clothes, hopped on a plane in Norfolk and within a few hours, landed in another world.
I once read when Frank Baum wrote The Wonderful Wizard of OZ in the late 1890’s, he used Chicago as his inspiration for the Emerald City. For me, that’s what Chicago became: a magical city of the mind, perfect in every way with skyscrapers glistening in the sun. A place for answers where dreams and wishes could come true.
I can remember pulling that old Samsonite through O’Hare Airport to the Blue Line of the subway system and struggling to maneuver it onto the train. I chose a seat next to the window so I could take in all the sights on the way to our hotel in downtown Chicago. Emerging from the innards of the airport station out into the blue sky and cityscape of Chicago was one of the most memorable moments of my life. In less than a few hours, through the miracles of modern transportation and time zones, I went from my bedroom to another world.
My only knowledge of Chicago was from watching the 1970’s sitcom Good Times with JJ and his family. The funny thing is, that’s exactly what Chicago looked like to me when our train started going through some of the neighborhoods and old housing projects. The graffiti everywhere was amazing to my teenage brain, so colorful and cool. The train moving along the elevated track making its way downtown provided a powerful first impression of the city.
I can remember the L train going right next to someone’s kitchen window and I could see an old woman in her tent dress standing next to a small stove with a frying pan cooking up something for breakfast. From the second I sat down on that ride along the track, Chicago was my favorite place. It was so different from my suburban landscape in Virginia Beach. I loved the closeness of the houses, the smoke and steam rising in places, the activity going on everywhere, and the massive downtown cityscape full of buildings, old and new, shining in the morning light in the distance.
When we finally got off the train, we were still a few streets away from our hotel, and we found ourselves in the middle of dozens of skyscrapers. We were quite the sight, a group of teenage boys from the beach with shorts on, lugging our suitcases through downtown Chicago in the cold of one of winter’s final morning rush hours packed with people going to work. After a few blocks of precariously making our way through the brick, steel, and glass wonders of Chicago’s modern and classical architectural wonderland, we finally arrived at the entrance to our hotel. Little did I know what was waiting for me on the other side of the revolving doors of the Palmer House Hotel.
We walked into the hotel lobby and my world changed for the second time that morning. I had never seen such space and luxury. Stairways and escalators. Trees and plants. Beautiful carpets and paintings. I was blown away. It was so luxurious. It smelled rich. It was alive with possibilities. It felt like a place for Presidents and gangsters. As I would later learn, it was; the Palmer House was once a gathering spot and a watering hole for some of Chicago’s most notorious criminals and has provided a night’s rest for nearly every President for the last 120 years.
Our chaperone, Mr. Willis, checked us into our rooms and gave us our keys. He said we could go anywhere we wanted WITHIN the hotel but we could not go OUTSIDE the hotel without him. Well, within ten minutes of checking in, we walked out into our floor’s hallway to explore and saw a door that said EXIT. We were up on one of the highest floors of the hotel and when we went to press the heavy door open, it was difficult to move. It took three of us to finally open it up. When we did, we tumbled out onto the fire escape and watched the door slam shut behind us. We immediately knew we had a mistake.
The wind was so intense we gripped the black iron all around us with white knuckles. The contrast between the quiet and the calm of the hotel hallway and the cold and wind we were now experiencing on the other side of that door was shocking. As teenagers not knowing any better, we were thrilled. We were in downtown Chicago nearly being blown away off a fire escape listening to the sounds of the city loving every minute of it.
Right up until we heard the door open and a police officer screaming at us to get back in the building.
The officer with his city accent was incredulous at our stupidity. He said “You know Chicago is called the Windy City for a reason, right? It can blow you all right off those balconies. Get in here and don’t do that again.”
We returned to our hotel room a little shook but still excited about what we just did and ready for more adventures. We took the elevator down to the lobby absorbing more of the beauty and opulence of the hotel. We started to see other people our age arrive from other Boys and Girls Clubs across the nation. For a teenager, this was heaven: a new city, a gorgeous hotel, freedom and independence away from home, and tons of boys and girls our age checking each other out waiting for the conference to begin.
As we walked from meeting room to meeting room, we ran across a group of girls. Our surfer styled clothes in the dead of Chicago’s freezing winter stood out and we got a few stares. I caught eyes with one of the girls from the group and in the goofy and direct way teenagers sometimes communicate with no introductory remarks, I asked for her name. She came over and told me her name was Patti. She was from a Boys and Girls Club in Chicago. Patti had short black hair, braces, and a kind smile. She was part Polish and part Japanese. She had a strong sense about herself and welcomed me to her city.
On my first day in Chicago, I managed to fall in love with a city and now, a city girl. After our brief conversation, she and her friends ran away, and I would spend the next two days at the conference trying to find her again.
I was so lovestruck, you might want to sit down for this mistake as it’s revealed, I didn’t even go to the scheduled Chicago Bulls game with their new rookie from North Carolina, Michael Jordan, because I didn’t want to miss a chance of running into Patti again. I walked all over the hotel, missing session after session, hoping our paths would cross.
When I finally did see her again, it was at a dance sponsored by the Boys and Girls Club on the last night of the convention. We danced and talked for two hours, gave each other our home addresses and an innocent peck on the cheek, then said goodbye. It was the type of teenage encounter that sadly seems impossible in our phone obsessed socially connected world today. If Patti and I met today, instead of in 1984, we probably would just text each other. No need to ever actually meet in person.
But it was the 1980’s so, over the next two years, Patti and I would write each other dozens of times. Inside one of her perfumed and decorated envelopes, she sent me one of her baby rings which I wore on a necklace for a time in middle school. I remember Patti always closed her letters to me with an acronym that I never fully understood until later. She would always end them with H.O.L.L.A.N.D-Hope Our Love Lasts and Never Dies.
Although, our adolescent love did not last, my love for the beautiful city of Chicago and particularly, the Palmer House Hotel, continues today. Every time I have traveled to Chicago since I was 13, I have stayed at the Palmer House Hotel. In our next Substack, The Windy City Part 2, I look forward to sharing about those visits.