An Unforgettable Journey: Exploring the Best of Chicago’s Iconic Landmarks and Culinary Delights
After a whirlwind couple of weeks, my travel diary has accumulated some incredible stories, and I’m thrilled to finally share them with you. In a span that feels impossibly short, I’ve ventured to California, celebrated my bridal shower, explored the vibrant metropolis of Chicago, and completed a 700-mile drive back home to Washington, DC. It’s been a crazy, food-filled, and utterly amazing adventure, even if my jeans feel a little snugger!
While my California tales are still waiting to be told (those who follow me on Instagram might have an idea of what that entailed!), let’s dive into my most recent escapade: an unforgettable trip to Chicago. This visit was more than just a getaway; it was a potential glimpse into our future.
A City of Possibilities: Navigating Life’s Big Decisions in the Windy City
As you may know, my fiancé, Connor, has been immersed in hospital rotations across the country, including exciting stints in San Francisco, New York City, and most recently, Chicago. This intense period is all part of the residency application process, a challenging journey that leaves medical students with little control over where they’ll end up. We’re currently in a thrilling, yet daunting, state of limbo, with our future home to be revealed on ‘Match Day’ – March 20th. For me, it’s also ‘Eat My Feelings’ day!
My inner control-freak is definitely on high alert, but there’s an undeniable excitement to it all. How often does life hand you an envelope that dictates where you’ll live for the next five years? It’s a truly unique blend of exciting, terrifying, and completely nuts! And if that wasn’t enough, we’re also in the thick of planning our wedding amidst all this uncertainty. Some might say we’re insane, and honestly, they wouldn’t be entirely wrong!
Given the possibility of making Chicago our new home, I knew it was essential to experience the city firsthand. Connor wrapped up his rotation on Friday, and I flew in on Sunday morning, fresh from my bridal shower, ready to explore for three days. Our adventure began with an early breakfast at Toast in Lincoln Park, fueling us for a journey to the heart of downtown Chicago: Millennium Park.
Iconic Chicago Attractions: From Cloud Gate to Sky-High Views
Millennium Park and the Reflective “Bean”
Our first major stop was Millennium Park, home to one of Chicago’s most iconic landmarks, Cloud Gate, affectionately known as “The Bean.” This highly reflective public sculpture offered endless photo opportunities, capturing the stunning city skyline and the vibrant park life in its mirrored surface. It’s a truly mesmerizing piece of art that invites interaction and leaves a lasting impression, a perfect introduction to the architectural marvels Chicago has to offer.
Soaring Above the City: The Willis Tower Skydeck
Next, we ventured to the legendary Willis (formerly Sears) Tower. A quick 103-floor elevator ride took us to the Skydeck, offering unparalleled panoramic views of the city. While I usually steer clear of overly touristy spots, I’m incredibly glad we made an exception for this! The breathtaking vista provided a profound understanding of Chicago’s sprawling layout and impressive scale. It was also fascinating to learn that the Sears Tower held the title of the world’s tallest building for over 25 years. We could even spot the wire meticulously constructed for Nik Wallenda’s daring high-wire walk, which coincidentally took place that very evening!
For an extra dose of adrenaline, Connor convinced me to step onto the Skydeck Ledge – a series of all-glass boxes that extend five feet out from the building, offering a thrilling view straight down. Despite my complete terror (I refused to look down!), I somehow managed a smile for the photo below. He even made me sit down on it – the power of peer pressure is real, folks!
A Culinary Journey: Indulging in Chicago’s Famous Deep-Dish Pizza and Fine Dining
The Ultimate Deep-Dish Experience: Giordano’s
To compensate for my terrifying Skydeck experience, Connor treated me to my very first Chicago stuffed pizza at Giordano’s, just around the corner. I must confess, I spent a good 45 minutes researching Chicago pizza in the weeks leading up to this trip. It’s a fiercely debated topic among locals (and I quickly learned the distinction between “deep dish” and “stuffed”!), with countless contenders vying for the top spot.
We shared a classic stuffed pizza, generously loaded with spinach and garlic. I was pleasantly surprised by the crust; I’d expected it to be heavy and greasy, but it was remarkably light and delicate, almost like a savory, cracker-like pie crust. It was an absolutely delicious and satisfying experience that solidified my appreciation for this iconic Chicago dish.
A Coastal Detour: Evanston’s Charm
After lunch, we took a drive to Evanston to visit Northwestern University, my mom’s graduate school alma mater. We explored the beautiful campus and even found my parents’ first apartment building. A walk along the stunning (albeit freezing) beach concluded our visit. Unfortunately, we’d completely forgotten about daylight savings, and the sun set a mere ten minutes after our arrival – a minor logistical oversight!
An Evening of Culinary Delight at Lula Café
That night, we indulged in an incredible dinner at Lula Café in Logan Square. While my photos were unfortunately terrible due to the low lighting, the meal itself was nothing short of spectacular. It was easily one of the best dining experiences of our entire trip. We savored a raw Brussels sprouts salad with Asian pear and cashews, kabocha squash and aged gouda croquettes, perfectly roasted duck breast, and an amazing eggplant and ricotta stuffed casoncelli pasta with veal bolognese, hazelnut, fennel, and parmesan. Each dish was a masterpiece of flavor and texture.
To top it off, the restaurant, despite being open for over 15 years and a true institution, apologized for a minor reservation mix-up by treating us to sparkling wine and a complimentary dessert. Such attention to detail and exceptional service, combined with outstanding food, truly left us impressed.
Chicago’s Architectural Marvels: A River Cruise Perspective
The following day began with a quick breakfast before heading to Wacker Drive and Michigan Avenue for the highly anticipated Chicago Architecture Foundation River Cruise. This tour had been on my “must-do-in-Chicago” list for years, and it absolutely lived up to the hype!
The cruise, which navigates all three branches of the Chicago River, was simply wonderful. The weather was perfect for November, hovering around a comfortable 60 degrees, and our guide possessed an incredible depth of knowledge about the city’s rich architectural history. I’ve always been drawn to impressive city skylines, especially those graced by a body of water, and Chicago’s did not disappoint. Learning about the vision and intricate thought processes behind the design of its iconic buildings, including Trump Tower, was absolutely fascinating. This experience deepened my appreciation for Chicago far more than I had ever anticipated.
A Whiff of Sweetness: Blommer Chocolate Company
During the cruise, I turned to Connor, exclaiming, “Oh my gosh, I smell chocolate!” Moments later, our guide confirmed my suspicions, announcing that we had just passed the Blommer Chocolate Company. Located on West Kinzie Street in River West, Blommer is the largest cocoa processor and chocolate ingredient supplier in the United States. The air literally smelled, and almost tasted, of rich chocolate! I’ve now decided that I need to move to that neighborhood solely for the pleasure of being enveloped by that incredible aroma all day long. It was truly a delightful sensory experience.
Exploring Modern Flavors and Hipster Hangouts
Unexpected Culinary Delights at LYFE Kitchen
After the boat cruise, our plan was to grab lunch at XOCO, Rick Bayless’s acclaimed Mexican street food restaurant, a recommendation from my older sister. We quickly discovered it was closed on Monday (don’t worry, we revisited it later!), so we wandered around the corner and stumbled upon LYFE Kitchen. Though I later learned it’s not exclusive to Chicago, we were thoroughly impressed!
LYFE Kitchen offers a concept of “slow fast-food,” focusing on seasonal, local, and often organic ingredients, with all dishes under 600 calories. It was the perfect healthy and delicious stop. We shared a fresh kale Caesar salad, roasted Brussels sprouts, and butternut squash. I particularly enjoyed my Barramundi soba noodle bowl, featuring mushrooms, scallions, and edamame in a warming kimchi broth – ideal for a chilly, overcast day.
Merchandise Mart and Wicker Park Adventures
Following lunch, we took a quick trip to Merchandise Mart, where I reveled in the world’s largest collection of showrooms, especially the kitchen displays. I even snapped a few photos before realizing it wasn’t allowed – oops!
Our afternoon concluded with a metro ride to Wicker Park in pursuit of donuts (priorities, right?), only to discover they were located just two blocks from our lunch spot, a classic travel miscalculation! Instead, I settled for a delicious pick-me-up cappuccino at Worm Hole Coffee. This super-hipster area, with its unique vibe, strongly reminded me of downtown Oakland and Berkeley, California. Clad in my new skinny corduroy pants, I felt perfectly at home in the vibrant atmosphere.
A City That Captivates
My first few days in Chicago were a whirlwind of iconic sights, incredible food, and unexpected discoveries. From the dizzying heights of the Willis Tower Skydeck and the reflective beauty of Cloud Gate to the deep flavors of a stuffed pizza and the stunning insights of the architectural river cruise, Chicago proved to be a city that truly captivates. Its blend of historical grandeur and modern vibrancy, coupled with its potential as a future home, made this trip particularly special.
Stay tuned for more updates, including a recap of our amazing dinner at The Girl & The Goat, and a detailed account of our final day exploring more of Chicago’s hidden gems!