A Perfect Weekend in Chicago: Architecture, History, and Deep-Dish Pizza

Exploring the heart of the Midwest is always a thrilling experience, especially when you are visiting a city as vibrant and historically rich as Chicago. Even though a sweltering heat wave was sweeping through the region this week, I recently had the wonderful opportunity to spend a few days in the “Windy City” with my son. Chicago is a city that never fails to impress, offering a unique blend of towering skyscrapers, lush green spaces, and a culinary scene that is famous around the world.

While I have had the pleasure of visiting Chicago’s world-renowned museums many times—from the Art Institute to the Field Museum—this trip was destined to be different. My son decided to take the lead on our itinerary and suggested something truly special: an architecture and historical Chicago river boat tour. This experience turned out to be absolutely fantastic, providing a perspective of the city that you simply cannot get from the sidewalk. If you are planning a trip to Chicago, I highly recommend adding this tour to your “bucket list.” It is an educational and visually stunning way to spend an afternoon.

The Magic of the Chicago River Architecture Tour

The Chicago River is the lifeblood of the city, and cruising along its waters offers a front-row seat to some of the most iconic structures in the world. As we boarded the boat, the gentle breeze off the water provided a much-needed respite from the intense Midwest sun. The tour guides are incredibly knowledgeable, sharing stories of the Great Chicago Fire and how the city literally rose from the ashes to become a pioneer in modern skyscraper design.

As the boat glides through the different branches of the river, you are surrounded by a diverse array of architectural styles, ranging from Art Deco and Neoclassical to the sleek, glass-heavy designs of the contemporary era. It is a testament to the city’s commitment to innovation and beauty. Every turn of the river reveals a new masterpiece, each with its own story of ambition and engineering excellence.

One of the most fascinating aspects of the tour is learning about the “Chicago School” of architecture. This movement, which emerged in the late 19th century, introduced the world to the steel-frame skyscraper. Seeing these historic buildings standing tall alongside modern giants like the Willis Tower creates a visual timeline of American progress. The way the buildings reflect off the surface of the river adds a magical quality to the entire experience, making it a photographer’s dream.

The Aqua Building: A Masterpiece of Modern Design

Among the many incredible sights we encountered, one building stood out as a true marvel of modern engineering: the Aqua building. This year, it won the award for the best architectural design in the world, and it is easy to see why. Designed by the talented Jeanne Gang, the building is a stunning example of how nature can inspire urban construction.

The Aqua building is famous for its unique undulating balconies. From a distance, the exterior looks like a series of flowing waves or cascading waterfalls. According to our guide, the design of these balconies was specifically intended to imitate the rhythmic waves of Lake Michigan. This organic shape isn’t just for looks; it also serves a functional purpose, breaking up wind gusts and providing residents with spectacular views while maintaining privacy.

The “Aqua” building won the best architecture design award in the world this year! The design of the balconies imitates the waves of Lake Michigan.

A City in a Garden: Greenery and Life Along the River

While the steel and glass structures are impressive, Chicago also lives up to its official motto, “Urbs in Horto,” which means “City in a Garden.” Despite the urban density, the city is filled with vibrant colors and natural beauty. Throughout our tour, I was struck by how much care is put into the landscaping along the riverbanks and city streets.

Flowers are everywhere in Chicago. You can see them lining the riverwalk, hanging from balconies, and decorating the walkways. This infusion of nature makes the city feel welcoming and alive. It creates a beautiful contrast between the rigid lines of the skyscrapers and the soft, organic beauty of the blooming petals. It is truly a city to be proud of, balancing industrial power with environmental aesthetics.

As we continued our journey, we saw many outdoor patios and cafes filled with people enjoying the atmosphere. The Riverwalk has become a hub of social activity, where locals and tourists alike gather to eat, drink, and soak in the views. It’s the perfect place to sit back and watch the world go by.

The river itself is a playground for many. In addition to the large tour boats, we saw numerous kayakers navigating the waters. Seeing people paddling right in the middle of a major metropolis is a testament to how well Chicago has integrated recreation into its urban planning. It looked like a fun and active way to enjoy a sunny day in the city.

Kayakers out on the river enjoying a beautiful, sunny day in the heart of the city!

Iconic Landmarks: The Sears Tower and Beyond

No trip to Chicago is complete without acknowledging the giants that define its skyline. One of the most famous is the Sears Tower (now officially known as the Willis Tower). For many years, it held the title of the tallest building in the world. Its bold, black exterior and tiered design make it an unmistakable landmark that can be seen from miles away.

I managed to snap a photo of my son on the boat with the majestic Chicago skyline and the Sears Tower looming in the background. It was a proud moment for me, sharing this experience with him in such a legendary location. The tour also took us past the Trump Tower and other glass giants that catch the light in different ways as the sun moves across the sky.

The architectural variety is truly staggering. You have the historic Wrigley Building with its clock tower and terra cotta finish, sitting across from modern towers that look like they are made entirely of mirrors. This blend of old and new is what gives Chicago its unique character. It is a city that respects its past while constantly looking toward the future.

The Culinary Grand Finale: Chicago Deep-Dish Pizza

After a long day of sightseeing and taking in the architectural wonders of the city, we worked up quite an appetite. There was only one way to end our Chicago adventure: with a world-famous, traditional Chicago treat. We headed to a local favorite to indulge in a delicious, out-of-this-world, super deep-dish and stuffed Chicago-style pizza!

Chicago pizza is unlike any other pizza in the world. It is more like a savory pie than a flatbread. The crust is thick and buttery, forming a deep basin that is filled with layers of gooey mozzarella cheese, your choice of toppings, and topped off with a thick, chunky tomato sauce. When we ordered the “stuffed” version, it came with an extra layer of dough inside, making it an incredibly hearty and satisfying meal.

The first slice is always a challenge to lift because of the sheer weight of the cheese and sauce! Every bite was a celebration of flavor. It was the perfect reward after a day of exploration. Sitting there with my son, enjoying the food and talking about the buildings we had seen, was the highlight of the trip.

As the legendary Frank Sinatra, also known as “Old Blue Eyes,” used to sing, “Chicago is my kind of town!” I couldn’t agree more. Between the stunning river views, the award-winning architecture, and the incredible food, it was a weekend to remember. If you ever have the chance to visit this magnificent city, take the boat tour, eat the pizza, and enjoy everything that Chicago has to offer. What a great weekend with my son!