For years, Chicago captivated my imagination, a vibrant metropolis I yearned to explore. That dream finally materialized in April 2019, when I had the incredible opportunity to host two dynamic events in the Windy City. This trip was an exhilarating blend of professional engagement and personal discovery, and I couldn’t be more excited to share the highlights and beautiful memories we captured below.
One of the greatest perks of traveling to new cities for work is the chance to extend the trip by a few extra days. This allows for dedicated time to delve into the city’s unique charm, either on my own or, even better, with my partner, Bridger, when his schedule aligns. Chicago, affectionately known as “Chi-Town,” certainly gave us a memorable introduction to its dynamic climate. In just five days, we experienced all four seasons! From a torrential downpour on our very first night to two glorious days of sunshine and warmth, followed by a dramatic thunder and lightning storm, and finally, extreme winds on our departure day. While I’ve heard such meteorological theatrics are typical of the Midwest, it nonetheless added an adventurous layer to our journey. Every moment, every unexpected shift in weather, simply made me more grateful for another incredible travel experience etched into our memory books.
Our first full day in Chicago kicked off with an iconic American experience: attending Opening Day at Wrigley Field, home of the legendary Chicago Cubs. The atmosphere was absolutely electric, brimming with palpable excitement and the cheerful camaraderie of passionate fans. It was, without a doubt, one of the best times we had. Naturally, we fully embraced the local culture by indulging in a classic Chicago-style hot dog, piled high with all the traditional fixings, as we settled into our seats directly behind home plate. The crack of the bat, the roar of the crowd, and the vibrant energy of the ballpark truly made for an unforgettable afternoon. After the sixth inning, we ventured just outside the stadium into ‘Wrigleyville,’ an expansive open turf area bustling with activity. Here, food trucks offered an array of delicious bites, and a massive big screen played the game live, allowing us to continue soaking in the excitement. This part, I must admit, was my absolute favorite. Being able to lay back on the soft turf, feel the warmth of the sun on my skin, and catch some much-needed rays felt utterly amazing, especially after enduring months of Seattle’s notoriously grey skies.
Exploring a new city is never complete without a culinary adventure, and Chicago certainly delivered on that front. We made sure to sample a wide variety of the local cuisine throughout our trip. Among the many delightful meals, Ema quickly emerged as our absolute favorite. This Mediterranean gem offered an exquisite dining experience with super fresh, incredibly flavorful dishes that left a lasting impression. We savored succulent kebabs, indulged in creamy, rich hummus, enjoyed warm, perfectly seasoned pita bread, and relished plates of briny olives and tangy feta. These classic Mediterranean flavors, expertly prepared, provided a refreshing and satisfying counterpoint to some of Chicago’s heartier fare. For those planning their own Chicago gastronomic tour, you’ll find even more of my top dining recommendations and hidden gems detailed in my comprehensive Chicago Guide – a must-read for any food enthusiast visiting the city.
One of the first things we noticed, and greatly appreciated, about Chicago was its remarkably flat topography. Coming from Seattle, a city characterized by its numerous hills and steep cross streets, navigating downtown Chicago felt like an absolute breeze. This made exploring the magnificent architecture and vibrant neighborhoods on foot incredibly enjoyable and far less strenuous. The city itself is truly gorgeous, a testament to stunning urban planning and historical preservation. The Chicago River, a central artery winding through the city’s heart, was particularly amazing. Its shimmering waters reflect the towering skyscrapers, creating breathtaking vistas at every turn. I can only dream of experiencing Chicago during St. Patrick’s Day one year, when the entire river is famously dyed a brilliant green – an event that must be truly spectacular. Equally captivating was Lake Michigan. Its sheer vastness and the presence of sandy beaches along its shores made it feel uncannily like an ocean, challenging all my preconceptions about inland lakes. It was a constant reminder of the incredible natural beauty seamlessly integrated into this bustling urban landscape.
For Bridger and me, sports are often a central theme around which we plan our travels. We share a deep love for experiencing different arenas and stadiums, believing it offers a unique window into the soul of a city through the energy and passion of its fans. Having both grown up playing various sports, it’s a shared interest that continually adds exciting entries to our growing list of games we’ve seen across the country. Naturally, a trip to Chicago wouldn’t be complete without catching a Bulls game at the iconic United Center. The atmosphere inside was electric, a pulsating symphony of cheers and chants from the devoted local fanbase. The Bulls were playing the Knicks that night, and though we were in Chicago, we proudly rooted for the New York team! It was a thrilling game, made even more exciting by the fact that the Knicks ended up clinching a victory in their second-to-last game of the season. The intensity of the crowd, the skill on the court, and the sheer joy of experiencing live NBA action made for another unforgettable evening.
Beyond the sightseeing and sports, the true heart of this Chicago journey lay in connecting with so many of you. As I mentioned earlier, the primary purpose of this trip was to host two incredibly special events. It was a profound joy to finally meet many of you in person, to engage in meaningful conversations about fitness, and to emphasize the indispensable role nutrition plays in our overall well-being. But perhaps the most exciting part was having the privilege of hosting my very first GOOD SWEAT group workout! This was a milestone I had been eagerly anticipating, a chance to bring my online community together for an empowering, in-person fitness experience.
Training such a large and enthusiastic group with exercises from my GOOD SWEAT workout program, which I launched earlier this year, was an absolute highlight of the trip. The energy in the room was electric, and seeing so many familiar faces – dozens of you whom I’ve connected with through Instagram – finally coming together in person was incredibly rewarding and immensely fun. There’s a unique magic in translating online connections into real-world shared experiences, and this workout session truly encapsulated that joy. A massive thank you is due to Hello Wellness for their invaluable partnership in bringing these events to life and meticulously organizing both gatherings. This marks our fourth collaboration, and each time, they flawlessly execute the vision, ensuring every detail is perfect – right down to providing amazing swag bags for all our wonderful guests. Their dedication and professionalism are truly unmatched, and I adore working with them! xx
Both events proved to be truly unforgettable, and I was genuinely overwhelmed by the incredible turnout. Seeing so many amazing women, and a few good-spirited boyfriends who were happily dragged along, made the entire trip immensely worthwhile. These in-real-life (IRL) events are more than just gatherings; they are powerful affirmations of the community we’ve built. Connecting face-to-face, sharing stories, and sweating together makes my job a thousand times more fulfilling, injecting a vibrant energy into everything I do. It’s moments like these that remind me why I started this journey and how much I cherish the connections I’ve made.
Before finally heading home to Seattle, we made sure to save one of Chicago’s most iconic landmarks, “The Bean” (officially known as Cloud Gate) in Millennium Park, for our last day. It was the perfect culmination to an absolutely perfect day and week in the city. The reflective surface of the sculpture offered endless opportunities for playful photos and truly felt like a grand farewell from this magnificent city. Every aspect of this trip, from the work events to the spontaneous explorations, exceeded all my expectations. I am already dreaming of my next visit and can’t wait to return to Chicago! For more in-depth information on the most recommended spots in Chicago, including hotel stays, must-do activities, and dining suggestions, be sure to check out my comprehensive CHICAGO GUIDE. It’s packed with all the details you’ll need to plan your own unforgettable adventure.
xxRachael