The Windy City and Me

The roots of Chicago stay with you, no matter how many miles or years pile up. For me, that footprint started when I was eleven years old, living for four unforgettable months on South Kedzie Avenue with my Gramma Mary. Down on the Southwest Side, near Gage Park and Chicago Lawn, the city had a distinct, working-class grit. At eleven, that stretch of Kedzie was my entire universe. It was a world of brick two-flats, corner stores, and the constant, lively hum of the neighborhood. It was an eye-opening introduction to the real heart of the city. 

Years later, I returned to Chicago as an adult, but this time, the city showed us a completely different side of its character. 

My husband and I found a dream setup: fully furnished apartments rented without long-term leases, stocked with everything from the linens to the dishes. He lived there for three solid years, and I joined him for three incredible summers. The rest of the year, I was back in the SF Bay Area, homeschooling my daughter. But when the summer months arrived and she went off to camp, Chicago became my absolute escape. 

Our place sat within easy walking distance of the Magnificent Mile, featuring massive, floor-to-ceiling windows that looked right out at the skyline. The lake itself was out of view, but the John Hancock Center stood right there, an absolute architectural anchor in our wall of glass. From that high-up vantage point, the apartment became our own private theater for the elements. Front row seats for Midwestern thunderstorms were pure drama, and watching winter snowstorms swirl past the glass while we stayed warm inside was magic. On summer nights, we would watch the fireworks unfold in the distance; even from far away, the silent bursts of color reflecting off the dark skyscrapers felt like a private light show. 

Every single day, we fell under the city's spell. Walking the Mile became our drug. The summer weather was always absolute perfection: temperatures hovering in the mid-seventies with a refreshing, cool breeze cutting through the towering buildings. We would walk the whole damn stretch, pacing ourselves all the way to the historic Water Tower to check out the local vendors. Lunch was a carefree, retro ritual, usually sliding into a booth at Johnny Rockets for burgers, fries and chocolate malteds. 

Then, once a week, we had our grand tradition: supper at Hugo’s Frog Bar & Fish House. We never asked for a particular table; we just sat all over the place, getting a new perspective on that lively, gold-coast room every single week. 

It was a beautiful, intoxicating routine. Between the daily strolls in the breeze, the bustling energy of the streets, and the quiet sanctuary of our apartment under the gaze of the Hancock, we truly learned how to breathe in the best of the city. I loved every single minute of it.