Exploring the Windy City: An Unforgettable Chicago Travel Guide and Personal Journey

Hello everyone! I wanted to extend a heartfelt thank you for your incredible patience over the past couple of weeks regarding my posting schedule. Life has been an absolute whirlwind, and it’s truly hard to believe just how much has happened in such a short span of time. Within these last two weeks, I’ve journeyed from coast to coast, attending my own wonderful bridal shower, jetting off to explore the vibrant metropolis of Chicago, and then embarking on the remarkably long, 700-mile drive back home to Washington, DC. It’s been an exhilarating, food-filled, and utterly amazing adventure, even if my pants feel a little snugger now!

While I still have so many stories to share about my recent trip to California – (if you’ve been following my antics on Instagram, you might already have a hint of what that entailed!) – let’s first dive into the most recent chapter of my travels: my incredible visit to Chicago. This city truly captured my heart in ways I never expected, offering a blend of stunning architecture, rich history, and a culinary scene that left me utterly impressed.

As I’ve hinted at before, Connor has been incredibly busy, navigating hospital rotations in various cities across the country. In just the past four months alone, his medical journey has taken him to San Francisco, New York City, and most recently, Chicago. This intense schedule certainly explains my somewhat sporadic posting, doesn’t it? The residency application process for medical students is no easy feat. It feels like applying to a million different places, with very little control over where you ultimately end up. The uncertainty is palpable, and for someone who thrives on planning and organization, it’s a unique challenge.

Consequently, we currently have no definitive idea where we’ll be moving or living come next summer. This will all be revealed on March 20th – a day famously known as ‘Match Day’ for medical students, and which I’ve affectionately dubbed ‘Eat My Feelings’ day for myself! My inner control freak, to put it mildly, is currently experiencing a mild meltdown. The thought of not knowing where our lives will lead is both thrilling and absolutely terrifying. On the one hand, how many times in your life do you receive a single envelope that dictates your home for the next five years? It’s an undeniably exciting prospect. On the other hand, it’s completely nuts, and the anticipation is almost unbearable!

Did I mention we’re also in the midst of planning a wedding alongside all this chaos? It’s safe to say we might be a little bit insane. Okay, okay, we are insane. I mean, just look at the picture below – I certainly embody a wild, slightly unhinged look! For the record, it was blindingly sunny that day, and I wasn’t attempting to channel my inner sailor; I was simply battling the sun’s glare.

Given that I had never explored Chicago before, and with the very real possibility of us moving there, I decided it was high time I experienced the city firsthand. Connor wrapped up his hospital rotation on a Friday, and I flew out to join him that Sunday morning, fresh off my bridal shower, for a three-day immersion into the city. Our Chicago adventure began with an early breakfast at the charming Toast in Lincoln Park. Fuelled up, we then headed straight to the iconic Millennium Park in downtown Chicago. What followed were, predictably, a million pictures of the magnificent Cloud Gate, affectionately known as “The Bean.” Its reflective surface and unique shape make it an irresistible photo opportunity, constantly mirroring the city skyline and the bustling life around it.

From Millennium Park, our architectural journey continued as we walked over to the majestic Willis Tower, still widely known to many as the Sears Tower. We ascended 103 floors in a swift elevator ride to experience the breathtaking panoramic views of Chicago from the SkyDeck. While I typically shy away from overtly touristy attractions, I am incredibly glad we made an exception for this one. The view was absolutely incredible, providing an unparalleled understanding of the city’s vast layout and intricate grid. I also learned a fascinating fact: the Sears Tower proudly stood as the tallest building in the world for over 25 years! It was even possible to spot the wire that had been set up for Nik Wallenda’s daring high-wire walk, which, by a remarkable coincidence, was scheduled to take place that very night. The energy in the city was palpable!

My bravery, however, was truly tested when Connor insisted I stand on the Skydeck Ledge. This glass-bottomed box extends approximately five feet past the Skydeck, offering an unobstructed, dizzying view of the city directly below. Despite my absolute terror – I refused to look down for even a second – I somehow managed to force a smile for the photo below. He even made me sit down on it! The power of peer pressure is real, folks, even when facing a 1,353-foot drop!

To compensate for the fright, Connor wisely guided me to Giordano’s, just around the corner, for a late lunch and, more importantly, my very first authentic Chicago stuffed pizza experience. I must confess, I probably dedicated close to 45 minutes in the weeks leading up to this trip to researching the best pizza joints in Chicago. It’s a fiercely debated topic among Chicagoans (one in which I am certainly not an expert – for example, I always thought it was called deep dish, not stuffed!), and there are countless contenders for the title of “best.” We opted for a classic ‘stuffed pizza,’ sharing one between the two of us, with delicious spinach and generous amounts of garlic added on top. I had mentally prepared for a heavy, potentially greasy crust, so I was pleasantly surprised by how relatively light it was! ‘Light’ might not be the most accurate descriptor, but it certainly wasn’t the dense, gut-busting experience I’d imagined. It had a unique, savory, almost cracker-like pie crust texture. Does that even make sense? Perhaps not, but either way, it was undeniably good, a true Chicago culinary rite of passage!

After our satisfying pizza feast, we took a drive north to Evanston to visit Northwestern University’s picturesque campus, my mother’s graduate school alma mater. It was a lovely stroll down memory lane as we searched for my parents’ first apartment building and walked along the beautiful, albeit freezing, lakeside beach. We completely forgot about daylight savings time, and the sun dipped below the horizon a mere ten minutes after we arrived. A major photographic fail, but a charming experience nonetheless, offering a glimpse into Chicago’s vibrant suburban communities.

That evening, we ventured into Logan Square for dinner at the renowned Lula Café. My pictures from that night are atrocious due to the dim lighting, so I’ll spare you the visual, but trust me when I say the meal was absolutely wonderful! We dined at many fantastic establishments during our trip, and Lula Café easily ranked as one of my top two favorite meals. We indulged in a symphony of flavors, sharing a crisp raw Brussels sprouts salad with Asian pear, cashew, and sourdough, followed by delectable kabocha squash and aged gouda croquettes infused with turmeric, anchovy, and lemon verbena. The roasted duck breast, accompanied by red cabbage, sunchoke, white truffle, and crispy duck vinaigrette, was sublime. But the true star was an amazing eggplant and ricotta stuffed casoncelli pasta, served with veal bolognese, hazelnut, fennel, and parmesan. It was truly one of the best meals we’ve had in a long time. Furthermore, the restaurant, despite a slight mishap with our original reservation, went above and beyond, treating us to complimentary glasses of sparkling wine and a dessert to apologize. Any establishment that demonstrates such a high level of food quality and customer service after being open for over 15 years deserves immense commendation. We were genuinely impressed.

The following day, our Chicago exploration continued with a quick breakfast before heading down to Wacker Drive and Michigan Avenue to embark on the highly recommended Chicago Architecture Foundation River Cruise. This was a definite “must-do” on my Chicago list, having heard glowing reviews for years.

The tour itself was everything I hoped for and more, showcasing all three branches of the Chicago River. The weather was absolutely perfect, hovering around 60 degrees Fahrenheit, which made for an incredibly comfortable and enjoyable experience. Our guide was exceptionally knowledgeable, providing fascinating insights into the city’s iconic architecture and its rich history. I’ve always been drawn to a captivating city skyline, especially those situated near or on a body of water, and Chicago certainly delivered. This cruise truly made me fall for the city more deeply than I ever anticipated. The historical context and the sheer thoughtfulness behind the design of Chicago’s skyline and its magnificent buildings, including the prominent Trump Tower, were utterly fascinating.

At one point during the serene boat cruise, a delightful aroma wafted through the air. I turned to Connor, exclaiming, “Oh my gosh, I smell chocolate!” Sure enough, within moments, our guide confirmed that we had just passed the Blommer Chocolate Company. Located on West Kinzie Street in River West, it’s the largest cocoa processor and chocolate ingredient supplier in the United States. The air literally smelled – and practically tasted – like rich, decadent chocolate! It was an incredible sensory experience, so much so that I half-jokingly decided I needed to move to that neighborhood solely to be enveloped by that heavenly scent all day long.

Following our enchanting boat cruise, our original plan for lunch was to walk to XOCO, Rick Bayless’s renowned Mexican street food restaurant, a recommendation from my older sister. Unfortunately, we discovered to our dismay that it was closed on Mondays. (Don’t worry, we made sure to go back the following day to satisfy our cravings!). Undeterred, we ended up walking around the corner and stumbled upon LYFE Kitchen. While I later realized that LYFE Kitchen isn’t exclusive to Chicago (it originated in California and has multiple locations), we were thoroughly impressed nonetheless! It’s essentially a slow fast-food concept, where all dishes feature seasonal, local, and often organic ingredients, with each meal thoughtfully crafted to be under 600 calories. It was a refreshing and delicious alternative.

At LYFE Kitchen, we shared a vibrant kale Caesar salad and a side of perfectly roasted Brussels sprouts and butternut squash. For my main, I savored a truly delicious Barramundi soba noodle bowl, brimming with earthy mushrooms, fresh scallions, and edamame, all nestled in a savory kimchi broth. It was the ideal comforting meal for a slightly cold and dreary day. This healthy interlude was followed by a quick trip to the colossal Merchandise Mart, where I spent a considerable amount of time ogling over the world’s largest collection of showrooms. My particular fascination was with the kitchen showrooms, where I couldn’t resist snapping a few photos – only to later realize I wasn’t supposed to (oops!).

We concluded the afternoon with a quick metro trip to the eclectic Wicker Park neighborhood, primarily on a mission for donuts – because, you know, priorities! It was a bit comical when we realized the donut shop was only two blocks from where we had lunch earlier. Nevertheless, I settled for a wonderfully invigorating cappuccino at Worm Hole Coffee instead. This area boasted a super-hipster vibe, immediately reminding me of the vibrant downtown neighborhoods of Oakland and Berkeley, California. Thankfully, I was sporting a new pair of skinny corduroy pants, so I felt perfectly at home amidst the trendy atmosphere.

Stay tuned! I’ll be back very soon with a detailed recap of our unforgettable dinner that night at The Girl & The Goat, and all the exciting highlights from our final day exploring the magnificent city of Chicago!