Embracing the Windy City: Our First Two Months of Life in Chicago

It’s hard to believe, but we are just days away from marking two full months as official residents of Chicago! The time has absolutely flown by, and yet, in some strange way, it feels like we’ve been here much longer. There are still moments, though, where the reality hasn’t quite sunk in. I’ll be standing in line at the grocery store, and my eye will catch a glimpse of my Illinois driver’s license in my wallet. Each time, I’m forced to do a double-take, a silent affirmation that yes, I truly live in the state of Illinois now. It sounds almost absurd, but it’s the honest truth – the sheer newness of it all still surprises me.

Just the other day, I was arranging a work-related phone call and inadvertently scheduled it for EST (Eastern Standard Time). It wasn’t until the next morning that the realization dawned on me, prompting a quiet shake of my head. These little blips serve as humorous reminders of the significant shift we’ve undergone, a gentle nudge from the universe that our new life in the Midwest is indeed a permanent reality.

Gardens at The Art Institute

Settling In: The Initial Whirlwind and Finding Our Footing in Chicago

These past eight weeks have been a blur. On one hand, a part of me feels as though we’ve been living in Chicago for an extended period, so much have we explored and experienced. On the other hand, there’s a lingering sensation, a ghost of our previous life, that makes it feel like we’ll be packing up and moving back to DC in just a few months. Even now, with our apartment fully settled and a burgeoning routine in place, it feels immensely strange to think that we will absolutely, without any shadow of a doubt, be calling this city home for the next five years. This long-term commitment is a big mental shift, and while exciting, it takes time to truly embrace.

The transition hasn’t been entirely smooth sailing, 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, a combination of factors converging at once. The stark realization that our closest friends and family were no longer just a short drive away hit hard. This was compounded by fully processing the whirlwind of the past year: the intense anticipation of the residency match process, the joyous yet demanding planning of our wedding, the hunt for the perfect apartment, our unexpectedly adventurous honeymoon, and finally, the colossal task of packing and moving all our belongings. With no major milestones or exciting distractions looming on the horizon, the sudden quiet felt very strange and somewhat unsettling.

Adding to the initial challenge was Chicago’s uncharacteristic weather. June, it turned out, was reportedly the wettest June the city had seen in almost a century. For the first two weeks, it felt like it was either raining incessantly or perpetually shrouded in a depressingly heavy cloud cover almost every single day. This constant dampness certainly didn’t help lift spirits during an already sensitive period of adjustment.

With all that said, I am now completely relieved that life has finally settled down. The boxes are unpacked, the furniture is in place, and we’ve found a rhythm. I finally feel like I can truly focus again – on work, on exploring, and on simply living. It’s a wonderfully grounding feeling to move past the initial chaos and begin building a stable, fulfilling life here in the vibrant city of Chicago.

Our new neighborhood in the West Loop

The West Loop: A Culinary Haven and Walker’s Paradise

One of the aspects that has absolutely facilitated our smooth transition to Chicago is our incredible new neighborhood: the West Loop. We honestly cannot say enough good things about living here. It’s a truly dynamic and inspiring area, brimming with life and convenience. We are quite literally surrounded by an unparalleled array of incredible restaurants, charming coffee shops perfect for a morning brew or an afternoon pick-me-up, bustling farmer’s markets offering fresh local produce, and a variety of grocery stores, including even a local fish market. The best part? We can walk to pretty much anything and everything we need or desire. This walkability is a game-changer, fostering a sense of community and making daily errands feel like enjoyable strolls rather than tiresome chores. It’s an environment that is inspiring, tempting (especially with all the food options!), and wonderfully convenient all at the same time.

Without intending to disparage my hometown, Chicago’s food scene undeniably trumps DC’s in a big, big way. The sheer variety, innovation, and quality of dining options here are breathtaking. Even after two months of enthusiastic exploration, I have yet to experience a single disappointing meal in this city. It feels like new and exciting places are popping up every single day, making it an endless adventure for any food lover. From high-end dining to casual eateries and diverse international cuisines, the West Loop, and Chicago as a whole, truly caters to every palate.

Caprese Burrata Salad at Soho House

Exploring Chicago’s Waterfront: Lake Michigan and the Riverwalk

During Connor’s first few weeks in Chicago, his schedule was relatively lighter than it is now, which gave us a fantastic opportunity to explore the city extensively on foot. Our apartment is conveniently just over a mile from the iconic Millennium Park, making daily excursions to the lakefront a regular occurrence. We’ve walked down to Lake Michigan countless times, soaking in the breathtaking views. In fact, we even bravely ventured into the thick Fourth of July crowds a few weeks ago to watch the fireworks display near the harbor! While I generally dislike crowds, and have to admit that DC’s fireworks might still hold a slight edge over Chicago’s, the experience was still memorable.

North Avenue Beach

But seriously, Lake Michigan and the Chicago River are undoubtedly two of my absolute favorite features of this magnificent city. We’ve made our way up to North Avenue Beach to enjoy the sand and sun, and have extensively taken advantage of the newly constructed Riverwalk – which I consider one of Chicago’s finest urban amenities. Strolling along its beautifully landscaped paths, admiring the stunning architecture, and watching the boats glide by has become a cherished pastime. We’ve also been trying to walk along the Lakeshore Trail as much as possible, soaking in the refreshing lake breezes and panoramic cityscapes. We’re even planning to kayak on the river sometime soon, an adventure we’re both eagerly anticipating before the season changes.

Because, as the saying goes, winter is coming. And we want to maximize every moment of this incredible Chicago summer while we still can!

Rose Garden in Grant Park

Chicago Summers: A Season of Festivities and Flavors

It certainly helps that Chicago summers are nothing short of incredible! The weather is remarkably pleasant, with significantly less humidity and generally much more comfortable temperatures than what we were accustomed to in DC. Of course, I’ve never experienced any other season in this city, but the energy during summer is palpable. People are constantly out and about, clearly taking full advantage of every single sunny day. The city truly comes alive, and there is a lot going on.

Almost every single weekend, you can find vibrant festivals happening in various parts of the city, celebrating everything from music and art to food and culture. It honestly appears that people spend about 80% of their summer days lounging on restaurant patios, enjoying refreshing drinks, especially local craft beers, and indulging in delicious food. It makes you wonder, do people even work in Chicago during the summer? I’m not entirely sure! The atmosphere is simply infectious, pulling everyone outdoors to partake in the festive spirit and communal enjoyment that defines this time of year in the Windy City.

Cubs Game in Wrigleyville

Dining In and Out: Balancing Culinary Exploration with Home Cooking

Speaking of food, as you can probably imagine, we’ve certainly done a fair amount of eating since we moved here. With Chicago’s incredible culinary reputation, it’s hard not to! However, we have been trying to be mindful and limit our dining out to no more than once a week, at most. We’re strategically saving some of our restaurant adventures for when family comes to visit us – first in a week’s time, and then again later in September. Sharing these amazing dining experiences with loved ones will make them even more special.

It also helps immensely that our new kitchen is a dream to cook in, easily 10 times more enjoyable than the one in our last apartment. The increased space, better layout, and modern appliances have rekindled our love for home cooking. Plus, a fantastic bonus is that our apartment building boasts outdoor gas grills, perfect for enjoying the beautiful summer evenings and whipping up some delicious barbecue right at home. This balance between exploring Chicago’s diverse restaurant scene and enjoying comfortable home-cooked meals has been perfect for us.

The Loop

Building a Community: Unexpected Friendships in the Windy City

One of the most heartwarming aspects of our initial months here is that we’ve already been able to make a small group of friends in the city! As most of you already know, we literally knew no one in Chicago when we first learned we were moving here. Connor has a cousin who is moving here this month, and another cousin who lives about an hour away, but beyond that, our social network was virtually nonexistent. This made the prospect of moving to such a large city, especially when I work from home and don’t have the built-in social opportunities of a traditional office environment, feel quite daunting.

But, one of the most unexpected and wonderful blessings of blogging has been the ability to connect with incredible people – many of whom I now consider good friends – all over the country. Even before we had officially moved to Chicago, a few fellow local food bloggers graciously reached out to me. They offered invaluable advice, shared recommendations, and generally made the transition so much easier and less lonely. Their warmth and welcoming spirit truly made a difference.

Birthday Bubbles at City Winery’s Riverwalk Location

Since then, a wonderful small group of us – hi to Jocelyn, Kristin, and Nora! – have been meeting up regularly for dinner at various fantastic restaurants across the city. If you’ve been following along on Instagram, you’ve likely seen many photographs from our delightful culinary adventures together. These gatherings have been a real highlight of our Chicago experience.

Just last weekend, Kristin generously offered to spend my birthday with me while Connor was working. We headed to City Winery’s beautiful Riverwalk location for drinks and snacks. They accidentally served us exquisite French champagne instead of the Spanish Cava we ordered, which was a pleasant surprise! We spent three wonderful hours chatting, sharing charcuterie and cheese, and discussing everything from our experiences in culinary school to our jobs, life in general, and our collective anxiety about the impending Chicago winters. It was a perfect, relaxed celebration.

The week before, a few of us ventured to Le Colonial in the elegant Gold Coast neighborhood, seeking out some delicious Vietnamese cuisine. We always make a bit of a spectacle of ourselves by taking numerous photographs of the food (I’m almost embarrassed to admit what we did during our very first dinner together!). But it’s all part of the fun, allowing us to try all sorts of new dishes while chatting about everything under the sun, forming genuine connections in the process. Basically, I’ve found that people in Chicago are really nice and incredibly welcoming.

Vietnamese Feast at Le Colonial in Gold Coast

Dive Deeper into Chicago Life: Upcoming Posts and Your Recommendations

I’m genuinely planning on sharing many more Chicago-related posts in the near future! You can expect a mix of content, including detailed insights into our daily life here, photography-based posts showcasing the city’s beauty, comprehensive restaurant recommendations (because the food scene truly deserves it!), and even some restaurant-inspired recipes that you can try at home. If there’s anything specific about Chicago life, food, or experiences that you’re particularly interested in, please don’t hesitate to let me know in the comments or via email! Your input helps shape the content I create.

In the meantime, I’ve made it easier than ever to find all my Chicago content by starting a new dedicated “Chicago” blog page. You can conveniently access this page directly from the top menu on the blog! This central hub will allow you to see all my Chicago-related posts compiled in one easy-to-navigate location. Additionally, you can always access all my posts about the city by simply selecting ‘Chicago’ under my category menu on the right sidebar of the blog.

Of course, if you’re planning a visit to the city, or are simply curious and want recommendations on what to do or where to eat (though my personal experience is still growing!), please don’t hesitate to reach out to me directly. I’d be thrilled to share what I’ve discovered and help you make the most of your Chicago experience!