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How I Fell in Love with Chicago Again After Moving Neighborhoods

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I moved to Chicago in 2008. I first traveled to the city in June of that year to visit friends I met studying abroad. My friends spent the entire weekend selling me on moving here, and I didn’t need much convincing. I was 24, single, and genuinely excited to leave NYC for a cleaner, more affordable, and friendlier city.

What to do in Old Town Chicago 11

Fast forward a decade, and my husband and I settled in Old Town. As we spent 6 years in that neighborhood, my excitement toward Chicago faded. The neighborhood’s nightlife boomed. People ten years younger than us were flocking to the neighborhood by the busload on weekends. All of the sudden there were velvet ropes and lines outside bars. The entire vibe of the neighborhood shifted, and we didn’t like it. When we had moved to Old Town we thought we were moving to a family friendly neighborhood, but it has morphed into Wrigleyville, Jr.

There weren’t any nice places for us to have dinner in the neighborhood. (Before you say Topo Gigio, I’ve always been underwhelmed). We realized that when we wanted to go out, we headed to another neighborhood. That, and a new baby, signaled to us that it was time to leave the neighborhood.

I’ve talked about how we “dated” different Chicago neighborhoods, spending date nights and weekends exploring various neighborhoods looking for one that felt like home. 

I was somewhat reluctant, but we settled on Wicker Park. We chose Wicker Park because we love the restaurants and bars (more laid back ones where you can actually have a conversation). It’s very walkable and feels like a real family friendly neighborhood. The convenience of taking the Blue Line to O’Hare was another major selling point. We also felt like our money would go further in Wicker Park, when compared to other neighborhoods we were considering like Lincoln Park. Most importantly, we found a home that fit our long list of requirements: at least three bedrooms, a bathroom on the same floor as the kitchen, a private roof deck, ease of entry into the home with a stroller, etc.

We decided to buy new construction. Having say in the home’s finishes and not taking on renovations was a big plus. But, buying new construction meant waiting 14 months for our home to be constructed. Instead of moving before having a baby, we moved with a 7 month old. We made it work.

We moved in early 2021 and it felt like our whole lives changed. I didn’t expect the move to completely change my feelings toward Chicago. 

Changing neighborhoods is one thing. I hadn’t really thought about how that also meant we would also be getting an entirely new set of neighbors and how this would impact my mental health and overall well-being. That might sound overly dramatic. If it does, you probably haven’t dealt with neighbors who hurl four-letter insults via group text to the entire building. It was exhausting and stressful. I couldn’t leave our old building fast enough.

On the day we moved, in a snowstorm, during a pandemic, with a baby, while mean texts came flying at us from a former neighbor, a new neighbor came outside to help Charles shovel snow. It was a sign that we had arrived in a very different place.

It’s nice to have top-tier restaurants nearby. It’s even better to be surrounded by people we genuinely love spending time with. 

Three years after moving to Wicker Park, it feels more like home than anywhere I have lived in my adult life. I can’t walk more than two blocks without running into someone I know. I am involved in community organizations. Baristas and servers at restaurants know my regular orders. If Gwen isn’t with me, people ask about her. It’s like we found the Chicago neighborhood we belong in. Instead of constantly leaving and spending time in other neighborhoods, we are excited to go down the street to dinner or to grab a beer at the corner pub. It’s an easier, happier, way of life.


Monday 8th of April 2024

Thank you for sharing, Kit. My family and I have been living in NYC for the past 10 years and we've always considered the possibility of moving to Chicago. If we ever decide to make the move, I will certainly remember your post about your experience. I will make sure to check out the neighborhood you mentioned the next time we visit Chicago.

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