Embracing the Windy City: Our First Two Months Living in Chicago

It’s hard to believe that we’ve already completed two full months as official residents of Chicago! The time has flown by in a whirlwind, and honestly, sometimes I still forget that I’m living in the state of Illinois. It sounds completely absurd, but it’s the absolute truth. Every now and then, my eyes will catch a glimpse of the corner of my Illinois driver’s license in my wallet while I’m waiting in line at the grocery store, and I’m invariably forced to do a double-take just to confirm its reality. It’s a subtle, almost comical reminder of this significant life change, highlighting just how transformative moving to a new city can be.

Just the other day, I was arranging a crucial work-related phone call and meticulously planned it for Eastern Standard Time, completely forgetting the time zone shift to Central Time. It wasn’t until the following morning that the realization dawned on me, prompting a frustrated shake of the head. These little moments underscore just how deeply ingrained our previous routines and environments were, and how much there is to adapt to in our new home in the heart of the Midwest.

Gardens at The Art Institute

The Whirlwind Transition: From DC to Chicago Life

These past eight weeks have truly flown by at an incredible pace. There’s a curious duality to how I perceive our time here: one part of me feels as though we’ve been living in Chicago for a considerable while, having settled into a comfortable rhythm. Yet, another part of me still harbors a lingering sensation, almost like we’ll be packing up and heading back to D.C. in just a few months. Even now, two months later, it feels incredibly strange to fully grasp the certainty that we will undoubtedly be calling this vibrant city home for the next five years. This long-term commitment is a big shift, and it’s slowly, but surely, sinking in, bringing with it a sense of both permanence and excitement.

Our apartment now feels completely settled and personalized, transformed from an empty space into a true home base. We’ve spent a significant amount of time exploring various corners of the city, from the bustling downtown Loop to charming neighborhood pockets, and we’ve finally established a functional, enjoyable daily routine that balances work and exploration. However, it hasn’t been a smooth journey filled only with “rainbows and butterflies.” In fact, about a week into our move, I definitely experienced a mini identity crisis. I felt utterly out of sorts, disoriented, and disconnected from my familiar self and surroundings.

This feeling was a potent combination of several factors: the stark realization that our closest friends and family were no longer just a drive away, coupled with fully coming to grips with the sheer craziness of the preceding year. The intense anticipation of the residency match process, the joy and stress of planning a wedding, the challenging apartment hunt, our unexpectedly adventurous honeymoon, and finally, the arduous tasks of packing, coordinating, and executing the big move. Once we were here, amidst the newness of Chicago, there were no grand events or major distractions looming on the horizon, creating an unsettling void. It felt incredibly strange to suddenly have this quiet after such a period of relentless activity, leaving space for introspection and a momentary feeling of being adrift.

Adding to the initial challenges, June reportedly marked Chicago’s wettest June in almost a hundred years. For the first two weeks, it felt like it was either raining incessantly or oppressively cloudy almost every single day, which certainly didn’t help lift spirits or make for easy exploration of our new surroundings. However, I’m immensely relieved that life has now found its equilibrium. I finally feel a sense of calm and, most importantly, I can truly focus again on my work, passions, and enjoying the vibrant city life that Chicago offers. It’s a profoundly good and welcome feeling to finally be settled and present.

Our new neighborhood in the West Loop

Discovering Our Urban Oasis: The West Loop Lifestyle

One of the elements that has absolutely facilitated our smooth transition to Chicago is our incredible new neighborhood: the West Loop. We honestly cannot speak highly enough about it. From the moment we step out our door, we are literally surrounded by an astonishing array of amenities and attractions. Imagine incredible restaurants offering every cuisine imaginable, charming independent coffee shops perfect for a morning brew, bustling farmer’s markets overflowing with fresh, local produce, diverse grocery stores (including a fantastic local fish market!), and the unparalleled convenience of being able to walk to pretty much anything and everything we could possibly need or want. It’s an inspiring, tempting, and utterly wonderful environment, all at the same time, making it the perfect base for urban living and exploring Chicago’s dynamic scene.

Without intending to disparage my former hometown, Washington D.C., Chicago’s food scene unequivocally trumps D.C.’s – and by a significant margin. In the two months we’ve been here, I have yet to experience even one disappointing meal, which is a testament to the city’s culinary excellence and the diverse options available. It genuinely feels like new, exciting places are popping up every single day, from innovative fine dining establishments to cozy neighborhood bistros, making it an endless adventure for food lovers. The sheer variety, quality, and innovation here are truly remarkable, solidifying Chicago’s reputation as a world-class dining destination and a true paradise for gourmands.

Caprese Burrata Salad at Soho House

Embracing Chicago’s Waterfront: Lake Michigan and the Riverwalk

During Connor’s initial few weeks in Chicago, his schedule was relatively lighter than it is now, which allowed us ample opportunity to walk and explore the city extensively. Our apartment is conveniently located just over a mile from the iconic Millennium Park, home to the famous “Bean,” and we’ve taken countless strolls down to the magnificent lakefront. A few weeks ago, we even braved the massive Fourth of July crowds to catch the spectacular fireworks display near the harbor. While I generally have an aversion to large crowds, and in fairness, the fireworks in D.C. might have slightly trumped Chicago’s in my personal opinion, the experience was still memorable and quintessentially Chicagoan, a true taste of summer celebration in the city.

North Avenue Beach

But seriously, if I had to pick two favorite aspects of this incredible city, they would undoubtedly be Lake Michigan and the Chicago River. These waterways are not just scenic backdrops; they are vibrant arteries of the city’s life and recreation, offering endless opportunities for leisure and stunning views. We’ve made our way up to the lively North Avenue Beach, a popular spot for sunbathing and volleyball, taken full advantage of the beautifully constructed Riverwalk – which has quickly become one of my absolute favorite spots for a leisurely stroll, offering unique architectural perspectives – and have been diligently trying to walk along the picturesque Lakeshore Trail as much as possible. The views are breathtaking, the atmosphere is invigorating, and there’s always something new to see, from sailboats on the lake to kayakers on the river. We’re also eagerly planning to kayak on the river at some point soon, which promises a unique perspective of the city’s architecture and bustling energy, a truly immersive experience in Chicago’s urban landscape.

Of course, there’s always that little voice in the back of my head reminding me: winter is coming. Knowing the formidable reputation of Chicago winters, we’re determined to soak up every last drop of these glorious summer days and enjoy the outdoor activities while we still can, before the cold truly sets in and transforms the city into a winter wonderland (or a snowy challenge!).

Rose Garden in Grant Park

The Joys of Chicago Summers: Festivals, Patios, and Unrivaled Vibrancy

It certainly helps that Chicago summers are nothing short of incredible! The weather here is a stark and welcome contrast to D.C., offering significantly less humidity and generally much more pleasant temperatures, making outdoor activities a joy rather than a sweaty ordeal. While I haven’t yet experienced any other season in this city, the current summer vibe is undeniably infectious. People are constantly out and about, clearly making the most of every single sunny day, and there is a palpable sense of excitement with a lot going on across the city, from street performers to lakeside concerts.

It seems there’s a festival happening in various parts of the city almost every single weekend, celebrating everything from music and food to art and culture. This continuous stream of events fosters a lively, communal atmosphere, drawing residents and tourists alike to experience Chicago’s diverse cultural tapestry. Furthermore, it appears that during the summer, people collectively decide to spend a significant portion of their days – perhaps 80%, judging by observation – relaxing on restaurant patios, enjoying delicious food and refreshing drinks under the open sky. It makes one wonder: do people even work in Chicago during the summer? I’m not entirely sure, but the dedication to enjoying the warm weather and vibrant outdoor life is truly inspiring, creating an unforgettable summer atmosphere that truly defines the Chicago experience.

Cubs Game in Wrigleyville

Culinary Explorations and Building a Community in the Windy City

Okay, let’s talk about the eating! As you can probably imagine, we’ve certainly done a fair amount of culinary exploration since moving here. Despite the temptation of Chicago’s unparalleled food scene, we have been consciously trying to exercise restraint, aiming not to dine out more than once a week at most. This strategy helps us savor our experiences and also allows us to save some of our more extravagant restaurant-dining adventures for when family comes to visit us, both in a week’s time and later in September. It’s an exciting prospect to share our new city’s gastronomic delights with loved ones, making each dining experience truly special.

It also significantly helps that our new kitchen is at least ten times more enjoyable to cook in compared to our previous apartment’s kitchen. The ample counter space, modern appliances, and overall brighter ambiance make home cooking a pleasure. The added bonus of our apartment building having outdoor gas grills means we can easily enjoy al fresco dining and grilling, further encouraging us to cook at home and experiment with new recipes, making our culinary journey in Chicago a balanced one that combines both the joy of dining out and the satisfaction of preparing meals at home.

The Loop

Beyond exploring the city and its food, we’ve also been incredibly fortunate to already establish a small, wonderful group of friends here. As many of you already know, when we first learned we were moving to Chicago, we literally knew no one in the city, which can be a daunting prospect. While Connor does have a cousin moving here this month, and another cousin living just an hour away, beyond that, our network of friends and family in Chicago was non-existent. Making new connections can be particularly challenging when you work remotely from home, without the natural social interactions that come with a traditional office environment, so we truly appreciate every new connection made.

But, one of the most unexpected and truly significant blessings of blogging has been the incredible opportunity to connect with people – many of whom I now consider dear friends – all across the country. Even before we had physically moved to Chicago, a few incredibly kind and supportive fellow Chicago food bloggers reached out to me. They offered invaluable advice, shared local insights, and made our transition so much smoother and less daunting. Their welcoming spirit immediately made us feel less alone in this vast new city, providing a built-in community even before our arrival.

Birthday Bubbles at City Winery’s River Walk Location

Since those initial connections, a small group of us – including the wonderful Jocelyn, Kristin, and Nora – have gathered for delightful dinners at various restaurants across the city, exploring everything from trendy new spots to established local favorites. If you’ve been following along on Instagram, you’ve probably seen a bunch of photographs from our memorable evenings together, showcasing both the fantastic food and our growing camaraderie, highlighting the vibrant social scene available even to newcomers.

Just last weekend, Kristin generously offered to spend time with me on my birthday while Connor was working. We headed to City Winery’s picturesque River Walk location for drinks and snacks. Through a happy accident, they served us exquisite French champagne instead of the Spanish Cava we ordered, and we leisurely snacked on a delectable charcuterie and cheese board for three hours. During this time, we chatted about everything from our shared experiences in culinary school to our careers, life in general, and our collective anxiety about the impending Chicago winters. It was a perfect, relaxed celebration, offering a warm sense of belonging in our new city.

A few days prior, another group of us ventured to Le Colonial in the elegant Gold Coast neighborhood, seeking out delicious Vietnamese cuisine. We inevitably make a comical spectacle of ourselves by enthusiastically taking photographs of all the food – I’m almost embarrassed to even admit what we did during our very first dinner together! Nevertheless, it’s always a fantastic opportunity to try a wide variety of dishes and engage in lively conversations about absolutely everything under the sun, from blogging tips to personal stories. These gatherings have quickly become cherished moments, fostering deep connections and helping us feel truly at home in Chicago.

Ultimately, my overriding impression is that people in Chicago are really nice and incredibly welcoming, which has made all the difference in our initial experience here. Their warmth and hospitality have transformed what could have been a challenging relocation into an exciting new chapter filled with discovery and friendship.

Vietnamese Feast at Le Colonial in Gold Coast

Looking Ahead: Your Guide to Chicago Life and Culinary Delights

I’m genuinely excited to share many more Chicago-related posts with all of you in the coming months. These will encompass everything from deeper insights into daily life in the city and photography-based visual journeys, to comprehensive restaurant recommendations and even restaurant-inspired recipes that you can recreate at home. Please don’t hesitate to let me know if there’s anything specific you’re interested in learning about or seeing – your feedback helps shape my content and ensures I’m covering what you want to hear most about living in Chicago!

In the meantime, I’ve decided to launch a brand new dedicated “Chicago” blog page. You can now conveniently access this page directly from the top menu on the blog! This new hub will serve as a centralized location where you can easily find all of my Chicago-related posts in one place, making it simple to navigate and explore our experiences in this incredible city. Additionally, you can always access all Chicago content by selecting ‘Chicago’ under my category menu on the right sidebar of the blog, ensuring you never miss an update.

Of course, if you happen to be visiting the city yourself, or if you’re looking for personalized recommendations on what to do or where to eat – and naturally, my experience is still relatively limited, but growing rapidly – please don’t hesitate to reach out to me! I’d love to help guide you through some of the wonderful experiences Chicago has to offer, from hidden gems to iconic landmarks and, of course, the best culinary spots.