Chicago, the city of skyscrapers, deep-dish pizza, and where winters freeze your soul (and probably your dreams too). Our relationship? Well, it’s been more on-and-off than I’d like to admit. And yet, here I am, once again, back in the Windy City for round three. This has to be the final lap, right? Or at least, that’s what I keep telling myself. But let’s be real, Chicago and I have some unfinished business.

Let’s rewind to 2015: I was supposed to go back to Puerto Rico for my fall semester after the summer, but UPR, being UPR 🤷🏽‍♀️, canceled three of the five classes I was going to take that semester. The other two? Online — back when remote learning was like the Death Star: an idea that existed but felt light years away. With most of my semester up in smoke, Mayra and a friend, both always full of wild ideas, laughed and said, “This is your sign from the universe. You need to stay in Chicago and do an internship.” The crazy part? I actually listened to them.

The next day, I became the queen of LinkedIn, blasting out resumes like I was trying to fight off an army of Stormtroopers. Most places didn’t even bother to respond (classic), but one company, Paco Collective, got back to me faster than the Millennium Falcon in lightspeed. Before I knew it, I was saying, “I’m staying in Chicago this semester.” What started as a summer visit to my family and some of the OG Sobremesa Chicago crew turned into my first “big girl” internship in a city that was all hustle, deep-dish, and endless possibility.

Fast forward to 2016, and I was ready to make my mark. I made the move full-time to Chicago. No more testing the waters — I dove in headfirst, terrified but buzzing with excitement for what was to come. The thing is, I didn’t need the unpaid overtime grind because I was doing something way more epic: being a full-time babysitter and the PR & Community Manager for Sobremesa Chicago. Double life? Absolutely. But who needs a ramen budget when Sobremesa Chicago pop-up leftovers and Spencer’s endless meal prep had my back? Thanks, Spencer! Not to mention the best quesadillas in Pilsen from “La Trilita.” RIP to my favorite spot — you are missed.

And then, 2021 rolled around. After a pandemic-induced stint back in Puerto Rico — which, let’s be honest, was less tropical bliss and more 24/7 Zoom calls — I came back to Chicago early 2022. But it wasn’t the Chicago I remembered. My favorite restaurant in Pilsen had closed, Danny’s Tavern once the best place to DANCE 💃 🪩, my friends had either moved away or settled into new lives, and everything felt off. The magic of the city had been swapped for the kind of gentrification that makes you say, “Wait, was this always here?” Suddenly, I felt like a stranger in the city that once felt like home.

In Puerto Rico, I had become known as “la alcaldesa,” but ironically, my true network was always in Chicago. Every major opportunity, every meaningful connection I had built, it all came back to this city. It’s funny — people in PR see me as this connected, influential person, but Chicago is where my roots truly run deep. I’ve always felt like I belong here, despite all the detours along the way.

And then, the curveball: Texas🤠. That summer of 2022, I found myself in Austin — a city I never thought I’d fall for. But fall, I did. I started to see it as the fresh start I desperately needed. ATX felt like that new love interest that’s a bit quirky but has all the potential. I spent months overthinking whether I should make the move full-time, but eventually, I did what I always do: I jumped. In September 2023, I packed my bags and left behind the city that had defined so much of my adult life.

Texas was great… for a while. But as much as I loved the BBQ, the sunshine, and the laid-back vibe, there was a pull I couldn’t shake. Chicago had its hooks in me. Even though I had left behind what was technically my dream job in advertising. I wasn’t done with Chicago. Maybe I never will be.

So, now it’s October 2024, and I’m back. Am I crazy? Probably. Am I ready? I hope so. This city, for better or worse, has been the backdrop to some of the biggest moments in my life. It’s where I’ve grown, failed, succeeded, and been shaped into the person I am today. Sure, it’s not perfect, but neither am I.

Chicago is the place that gave me my first shot, even if it came with its share of hard lessons. It’s the city where I learned what I want, and more importantly, what I don’t want. And while Puerto Rico may call me la alcaldesa, Chicago knows me for who I really am

a hustler who’s always looking for the next move, always ready to reinvent herself.

So, why come back? Why not just stay in Texas or even Puerto Rico? The truth is, I’m not done with this city. Chicago is more than just a place on the map; it’s a part of me. I know its flaws, but I also know its beauty. I’ve seen the way it can challenge you, but I’ve also felt the rush of what it means to succeed here. And who knows, maybe this time, the city and I are finally on the same page.

La tercera la vencida? Maybe. Or maybe this is just another chapter in the ongoing saga of me and Chicago.

Whatever happens, one thing’s for sure: I’m back, Chicago. Let’s see what you’ve got this time.

Besiss

Génesis ❤️‍🔥🔥