Downtown Chicago, Illinois
122 W Monroe St, Chicago, IL 60603
Earlier this year, we took a (surprise) trip to Chicago to celebrate my husband’s birthday - a getaway centered around good food, long walks, and experiencing the city together at a slower, more intentional pace. Chicago felt like the perfect choice: vibrant, architectural, and home to some truly memorable dining experiences. We stayed downtown at the Kimpton Grey Hotel, a hotel I stayed at once before during a wedding work trip. The historic building, paired with the hotel’s warm, understated design, made it an inviting place to return to after full days exploring the city. Being centrally located allowed us to walk almost everywhere, which is often my favorite way to experience a place — observing details, neighborhoods, and small moments in between destinations.
- Kimpton Gray Hotel
- Proxi
- The Publican
- Willis Tower
- Downtown Pedicab
- The Navy Pier
- Chicago Architecture River Cruise
- Boka
- Cloud Gate at Millennium Park
- A special mention to Simons Jewelers St. Louis for helping select an incredible birthday gift
Proxi
Food was a major focus of this trip, and we planned our meals around a few restaurants on the Michelin Guide. One of our first stops was Proxi, a globally inspired Michelin Bib Gourmand restaurant that blended bold flavors with a lively atmosphere. While Proxi has since closed, I’m grateful we had the chance to experience it when we did — it felt creative, fun, and perfectly suited to the celebratory spirit of the weekend. Featuring their newly-launched Coastal Asian menu, we enjoyed several fusion dishes including a Wagyu beef searing stone experience that made our evening truly special.
The Publican
837 W Fulton Market, Chicago, IL 60607
The next day we enjoyed a brunch at The Publican, which offered a completely different, but equally memorable, experience. Rustic, cozy, communal, and full of character, it felt quintessentially Chicago. It was the kind of place where conversation flows easily and the food feels both comforting and elevated. Our hearty meal included the aged cheddar & herb biscuit, the Publican waffle, and an incredible red chili pork benedict that I still think about, to this day. Delicious.
Red Chili Pork Benedict
PQB sourdough, avocado, crispy pork belly, red chili chipotle sauce, queso fresco, pickled red onions, poached eggs
BOKA is a Michelin-starred restaurant offering seasonal American cuisine by Executive Chef Lee Wolen.
Boka
1729 N Halsted St, Chicago, IL 60614
Our special birthday dinner was at Boka, a one-star Michelin restaurant, and it was the highlight of the trip. The experience felt thoughtful and refined without being overly formal. Every course was beautifully composed, and the attention to detail — from the service to the pacing of the meal — made the evening feel truly special. It was one of those meals you linger over, savoring both the food and the moment.
Boka is a Michelin-starred restaurant in Chicago, Illinois, known for its refined yet approachable take on contemporary American cuisine. Led by Chef Lee Wolen, the restaurant emphasizes seasonal ingredients, thoughtful technique, and clean, elegant flavors. Set in a warm, intimate space in Lincoln Park, Boka offers a dining experience that feels both elevated and welcoming, making it a standout destination for special occasions and memorable meals.
The birthday gift, a Ronde Must de Cartier timepiece
Touring Downtown Chicago
After our belly-busting brunch at the Publican, we stepped outside into the early Spring chill to visit some of Chicago’s most iconic sights. We visited the Willis Tower (Sears Tower still a classic, no matter how many times it’s renamed) and took in the expansive views of the city stretching out below us. We even braved the Chicago Sky Deck - an experience that places visitors onto a 1.5 inch-thick glass ledge allowing one to truly appreciate the height of the building - a towering 103 floors.
Following our thrilling visit to Willis Tower, we enjoyed a fun pedicab trip to the Navy Pier to board a riverboat cruise. Before leaving for home, we had to make a quick visit to see Cloud Gate, a beautiful "bean" sculpture by Indian-born British artist Anish Kapoor, that is the centerpiece of Grainger Plaza at Millennium Park in the Loop community area of Chicago.
What it feels like to be 1,353 feet above the ground
A distant light fixture near the Navy Pier
Random things from our trip: a hotel coaster, treats from Boka, our Skydeck tickets, and personalized menus.
Reflections
Chicago gave us a weekend full of great food, important shared moments, and memories I’ll always associate with this birthday milestone. It’s a city I’ll happily return to, camera in hand, ready to wander again. This trip felt like the perfect balance of celebration and presence. It wasn’t about doing everything, but about choosing experiences that felt meaningful and enjoying them fully. Happy 45th Birthday, my love.
