Chicago Unveiled: A Culinary & Architectural Journey Through Oak Park and Beyond

Following an unforgettable first day in the Windy City, our second full day in Chicago promised—and delivered—just as much excitement, discovery, and gastronomic delight. This extensive exploration took us from a celebrated culinary hotspot to the hallowed grounds of architectural genius, culminating in a series of unforgettable meals that cemented Chicago’s place in our hearts. While Part 1 set a high bar, this leg of our adventure further revealed the city’s vibrant character and diverse appeal.

An Evening of Indulgence: Dining at Girl & The Goat

Before diving into the day’s main events, I simply must recount the previous night’s dinner at Stephanie Izard’s renowned restaurant, Girl & The Goat. We considered ourselves incredibly fortunate to have secured a reservation a few weeks in advance, a testament to its immense popularity and critical acclaim. The anticipation alone was a significant part of the experience.

Connor and I embarked on a shared plates adventure, a culinary journey through an innovative menu designed for communal enjoyment. By the end of the meal, we were completely stuffed, yet every single dish had been a revelation. While undeniably delicious, the cuisine at Girl & The Goat is known for its rich, bold flavors, and our selections certainly lived up to that reputation. We found ourselves in that familiar, delightful predicament: eating far too much in a valiant effort to sample as many intriguing dishes as possible. This is a common theme in our culinary explorations, especially when encountering a new restaurant of such caliber.

Our highlights included the pan-fried shishito peppers, perfectly charred and seasoned with parmesan, miso, and sesame, offering a delightful blend of savory and umami. The kohlrabi salad was a refreshing counterpoint, featuring delicate slices of kohlrabi alongside sweet pears, aromatic fennel, and earthy roasted shiitake mushrooms. We also savored the hamachi crudo, an artful presentation of fresh fish, and a country sourdough bread course served with a rich tuna and Nicoise tapenade. The grand finale, however, was the restaurant’s signature pig face dish, an iconic offering topped with crispy fried potato stix and a perfectly cooked sunny-side egg. This dish, truly a conversation starter, embodies the restaurant’s adventurous spirit.

For those curious about the “pig face,” it is exactly as it sounds – a culinary exploration of a less common cut. This Serious Eats post offers a detailed insight into its preparation, though be warned, it includes some graphic details for the uninitiated.

Journey to Oak Park: A Deep Dive into Frank Lloyd Wright’s Legacy

The following morning, still reminiscing about the previous night’s feast, we set out for Oak Park, a charming suburb just west of Chicago. Our primary mission was a highly anticipated tour of Frank Lloyd Wright’s personal home and studio. As an ardent admirer of architectural history and house tours in general, this experience was at the top of my list. We were fortunate to be part of a small group of fewer than five people, which made for an incredibly intimate and engaging tour experience, allowing for questions and a closer look at every detail.

The entire Oak Park neighborhood itself is simply gorgeous, and our visit coincided with the absolute peak of the fall foliage. Vibrant reds, oranges, and yellows painted the trees, creating a breathtaking backdrop for the iconic architecture. It was truly a feast for the eyes, enhancing the historical significance of our surroundings.

Having never had the opportunity to visit a Frank Lloyd Wright property before, this particular site held extra special significance. His home and studio in Oak Park is not just a residence; it is a living museum, showcasing the genesis of many of Wright’s revolutionary architectural philosophies, groundbreaking design concepts, and early experimental works. It’s where he first began to articulate his signature “Prairie Style,” an architectural movement deeply rooted in American landscapes and ideals.

While Wright is undeniably an iconic architect and designer, and I was familiar with photographs of his more famous properties like Fallingwater, my personal knowledge of his life and creative process was rather limited. This tour was therefore incredibly enlightening, offering a deeper understanding of the man behind the masterpieces. The guide’s insights brought his early struggles, inspirations, and innovations to life, making the historical context profoundly engaging.

Adding to the magic of the experience, the natural light streaming into the home was absolutely perfect for photography. I was in my element, snapping away at every intriguing angle and detail. What else is new, right? I had wisely invested in the ‘photography group pass’ option, which allowed me to capture the stunning interiors of the house. I took an abundance of photos; this post is already bursting with them, and I could easily have shared a million more! My enthusiasm was perhaps a bit much for our patient tour guide, who seemed ready to call it a day with my relentless shutter clicks. Seriously, though, every corner offered a new perspective worthy of a shot.

Of course, I made sure to photograph what I jokingly refer to as the most important room in any house: the kitchen. Well, kind of, sort of. For a food enthusiast, the kitchen often holds a special allure, even in a historical architectural masterpiece!

In addition to exploring Wright’s iconic ‘Prairie Style’ home, our tour also included a visit to his attached studio. This was the vibrant hub where he ran his entire architecture and design firm for many formative years. To attempt to describe the ingenuity of the space, its layout, and its design feels almost inadequate. It’s a profound testament to his creative genius, an undeniable understatement for a man who revolutionized modern architecture.

Exploring Historic Oak Park: A Wright Architecture Showcase

After our formal guided tour concluded, we took advantage of the beautiful autumn day to embark on a self-guided exploration of the surrounding historic Oak Park neighborhood. This area boasts the world’s largest concentration of Frank Lloyd Wright architecture, featuring seven other distinctive Wright-designed homes alongside his own residence. Each property tells a part of his evolving design story.

The entire neighborhood is incredibly picturesque, with tree-lined streets and an array of stunning, historically significant houses that collectively form an open-air museum of early 20th-century American architecture. It truly felt like stepping back in time, immersing ourselves in the aesthetic that Wright championed.

During our stroll, we may or may not have veered into Oak Park’s quaint downtown area and made an essential stop at a local bakery. There, we indulged in a heavenly slice of warm caramel and chocolate croissant bread pudding. Because, priorities, people! A little treat is always well-deserved after soaking up so much culture and history.

Also, I must confess, halfway through our leisurely neighborhood tour, my concentration was completely derailed by the sight of the world’s cutest yellow Labrador puppy. Such a typical occurrence for me! I instantly declared that I needed one. The charm of Oak Park offers both architectural wonders and adorable distractions.

A Late Lunch Masterpiece: Rick Bayless’s XOCO

By this point, it was nearly two o’clock in the afternoon, and I absolutely refused to miss the opportunity to dine at Rick Bayless’s acclaimed XOCO. I had heard so much about this place, and to my dismay, it had been closed the previous day. Missing it again was simply not an option. Thus, we drove all the way back into the city, specifically to the vibrant River North neighborhood, for a very late, but immensely anticipated, lunch.

Our culinary adventure at XOCO began with an order of chips and guacamole, served with an incredible array of toppings – a combination so perfect that I immediately made a mental note to recreate it at home! We then shared two tortas, each a masterpiece in its own right. First, the warm Woodland Mushroom torta, a symphony of flavors featuring chipotle-garlic mojo, creamy goat cheese, robust black beans, fresh arugula, and a zesty three-chile salsa. The second was the Ahogada torta – pictured at the bottom – a truly unique creation with golden pork carnitas, black beans, and pickled onion, all served on a crusty baguette. What makes the Ahogada truly stand out is its immersion in a spicy tomato and arbol chile broth, giving it an intensely flavorful and satisfying kick. It was impossible to pick a favorite; both were absolutely exquisite, showcasing the depth and complexity of Mexican cuisine.

My new, somewhat serious, goal is to move to Chicago just so I can systematically eat every single item on XOCO’s menu and eventually dine at all of Rick Bayless’s renowned restaurants. I’m barely kidding; the food was that transformative.

Many of you, through Instagram, had emphatically insisted that I try XOCO’s famous drinking chocolate during my visit, and naturally, I couldn’t resist. Especially after reading the enticing description on the menu. XOCO takes pride in roasting and grinding their own cocoa beans to craft all their signature drinking chocolates, ensuring an unparalleled depth of flavor. I opted for the Aztec hot chocolate, a rich concoction made with fresh-ground chocolate, fragrant allspice, and a hint of chile. The result was a surprisingly smoky, subtly spicy, and incredibly intriguing beverage – a distinct departure from any hot chocolate I had tasted before.

While I savored my unique hot chocolate, Connor, despite our substantial lunch, insisted we make a quick detour around the corner. His mission: a doughnut from Glazed & Infused, another fantastic recommendation from my wonderful followers (seriously, you guys are awesome!). It still baffles me how he managed to find room for a massive caramel pumpkin pecan doughnut. We even foresightfully purchased an old-fashioned doughnut to enjoy during our road trip the following day!

Evening Wind-Down & A Final Feast at The Purple Pig

We spent the remainder of the afternoon, which was relatively brief given it was already past 3 PM, strolling around the vibrant River North area, soaking in the city’s atmosphere. Eventually, we made our way back to our accommodation. There, I caught up on some work before promptly succumbing to an inevitable food coma nap, a testament to the day’s earlier culinary excesses.

Given the sheer volume of food we had consumed at our late lunch, our appetite for dinner didn’t resurface until almost 9 o’clock that night. Our chosen destination was The Purple Pig, a highly recommended Mediterranean small plates restaurant. After about an hour’s wait, we were lucky enough to secure a table, and the experience was well worth every minute. It truly stood out as one of the best meals of the entire trip, a delightful capstone to our Chicago culinary explorations (though, truthfully, every meal had been exceptionally good). The convivial atmosphere, coupled with the inventive dishes, provided a perfect ending to our time in Chicago.

Homeward Bound and Future Dreams

The next morning, with fond memories of Chicago still fresh, we rose incredibly early for the long drive back to Washington D.C., a journey spanning over 700 miles. It had been quite a while since I embarked on such a lengthy road trip, and I must admit, boredom set in after about four hours into the 11-12 hour drive. However, there were some notable highlights: we drove through a time zone, an interesting first for me! We also made a spontaneous stop to explore the beautiful campus of the University of Notre Dame, marking my first time in Indiana. To keep our spirits high, we listened to this hilarious audiobook by comedian Jim Gaffigan, which made the miles fly by with laughter.

It’s quite surreal to think that we might be making this exact trip again in just a few (way too) short months, potentially to search for a new place to live! The thought of returning to Chicago, perhaps even making it our home, is a truly exciting, and slightly crazy, prospect. The city has left an indelible impression, a whirlwind of architectural marvels, unforgettable flavors, and cherished memories that beckon us back.