As a kid growing up in the midwest, Chicago was always the goal. A mythical land of hotdogs, Lollapaloozas and cubby bears, it wasn’t even a choice for me. While most of my friends actively sought opportunities outside of the midwest, I was ecstatic to settle down and embrace the eclectic neighborhoods and miserable weather. Throughout the last five years I’ve had the chance to discover much I love and a little I hate, and what an incredible five years it has been.

Lincoln Park seemed like the obvious choice after graduation. We were close to everything I was familiar with and it felt like there was always a good weekend plan. McGee’s Fridays and Apartment Saturdays were replaced by the likes of Mad River, Headquarters and Kingston Mines. Late nights of Los Tres Panchos, the best burrito place in the city, became the normal dinner on weekends. Scotch flights and poutine at The Monkey’s Paw followed by rooftop cigars on sunny Sunday afternoons… not sure it gets any better.

Photo Credit: The Monkey's Paw

Photo Credit: The Monkey's Paw

And as we discovered new spots and attended more concerts and generally enjoyed being young, wild and free, I fell in love with the city all over again. Even after moving to northern Lakeview, a decidedly quieter place with less action and more cab fares, each week had a new brunch place or a different street festival waiting for us. Still, Chicago is not without its downsides. I know that complaining about the weather has become something of joke around here, but several straight months of bitter cold will break anybody. Street parking a car for two years will take twice as much time off your own life. Want to take a day trip to go hiking or skiing? Better off flying somewhere for a weekend.

Our last few years Jenny and I have lived in River North, by far the most convenient place to live. I wouldn’t say the neighborhood is completely devoid of any personality, but it is most certainly designed for tourists and young professionals working in the loop. We have had to travel for work much of the time we’ve lived here, but it hasn’t stopped us from continuing to explore and discover. Whether it be at Ming Hin in Chinatown or Avec in the West Loop, we’ve had an impressive culinary tour of the city. The food might be what I miss the most after we’re gone, although it might also be what I’m looking forward to the most as we travel around the world.

I will never forget my time in Chicago; it truly is one of the greatest cities in the world. For 3 months of the year, I actually don’t think it can be topped. It’s time to get out of my midwestern bubble, though. I’m not a particularly ambitious person, but I’ve seen the kind of self-improvements that present themselves when I’m out of my element and trying something new. I’d like to continue building on that even after travel, get to know and love a new city as much as I love Chicago. Yet as we take our last summertime strolls down the lakeshore path and through the busy streets, I can’t help but think this city isn’t quite done with me for good.


I moved to Florida when I was 9, but I spent my earliest years in the suburbs of Chicago. After I moved away, I spent the next nine years plotting a way to get back. My Florida hometown is tiny and slow-paced and the complete opposite of a big city, and I was determined to escape it. I knew what city life was like (at least as much as a fourth-grader can understand that) and so I built up this idea in my head that moving to Chicago would mean that I’d finally have my life figured out.

Now I’ve been here for the better part of a decade, and I can safely say that while I don’t have everything totally figured out, I think fourth-grade me would be pretty proud of the life I’ve made here. It’s time to move on to bigger and stranger things, but I’m grateful to this city and its chaos and beauty and, yes, even its horrific winters.

It’s embarrassing to admit, but I really didn’t venture into the city all that much until my senior year at Northwestern. I wasn’t good at navigating downtown El stops or figuring out which neighborhood my favorite bars were located in - I’d typically just follow my friends or jump in a cab, so my spatial understanding of the city didn’t really develop until I moved downtown after graduation.

The one exception to that fact was the museum campus. As a kid I spent countless hours at the Field Museum, and to a lesser extent the Shedd Aquarium. Some of my fondest memories of my childhood involve running around the mummy exhibit at the Field, sprinting down the spiral stairs into a pharaoh’s tomb and ogling the hieroglyphics, imagining I was an Egyptologist deciphering clues about this person’s life. Maybe that’s weird, but it’s also very indicative of what kind of child I was. That’s why on the rare occasions that I felt courageous enough to take the train downtown by myself as a freshman or sophomore, it was inevitably to make the trek to the Field and relive my childhood. Even now, after dozens of visits and even more hours spent, there’s still something magical about spending a day getting lost in the exhibits and exploring the relics of cultures long-gone. No matter how old I get or how long I’ve been away, the Field will always be in my plans when I visit Chicago.

The real story of my love affair with Chicago, though, begins after graduation, when I moved into my first (and second) apartment in Lakeview. That first year of adulthood flew by in a whirlwind of Wrigleyville bars (Sluggers, I will always love you), late-night burritos, weeknight trivia and weekends at Ryan Field. Those were the glory days: young enough to avoid hangovers; old enough to pay my bills. Living right off of the Red Line afforded me the ability to finally develop a sense of place within the city, and I began to explore some of the neighborhoods that give Chicago its unique character.

After Lakeview, I moved to the Southport Corridor, which has changed so much in the few years since I’ve lived there that I hardly recognize it anymore. Even in River North, where I live now, I’ve seen beloved businesses close and new high-rises go up in the blink of an eye. I guess that’s one element of Chicago that fascinates me: for better or worse, this city is constantly evolving. But there are a few things that, in my eyes at least, will never change. They’re mostly just feelings, like that first warm, sunny day of spring where everyone suddenly bursts from their hibernation all at once, donning shorts and taking to the lakeshore path in massive numbers. It happens every year, and it reminds me that despite the soul-crushing winters we have to suffer through (and trust me, they are just as bad as you’ve heard), this city is at its absolute best in the summer. With rooftop bars on every corner and festivals and street fairs every weekend, you’d be crazy to feel bored between Memorial Day and Labor Day. I think the winter gives us character: we suffer through polar vortexes and black ice and frigid winds so that we can earn our time in the sun, and we’re stronger for it.

I guess that’s what I’ll miss most about Chicago: not a specific place, although there are so many places in this city that will be in my heart forever. More than anything, I’ll just miss the feeling of living in the heart of such a vibrant city. Any direction you walk, you’re bound to find something new and exciting just around the corner. Whatever mood you’re in, there’s a place for you. It’s welcoming and warm and the people are friendly. Even as a fourth grader, I understood that feeling, and as an adult, after nine years here, I know for a fact it’s one of a kind. Goodbye Chicago, I truly love you.