I was recently in Chicago for DynamicsCon, a top-tier community event for users and implementers of Microsoft’s Dynamics platform–Like Me!
The conference was an excellent chance to catch-up with old friends, make new ones, and learn about the latest happenings in the world of Dynamics (If you’re curious, there are a lot of happenings).
DynamicsCon was also an opportunity to learn about Chicago.
I took in a Cubs game at Wrigley with some friends.
(Justin Turner hit a walk-off RBI for the win over the Marlins)
I also dropped in to train jiu jitsu at a local place.
(Serafin Jiu Jitsu is the most beautiful gym I’ve ever visited)
My Uber driver suggested the best way to learn about Chicago is to take an architecture boat tour–boats ferry you around the Chicago river and they tell you about the buildings. I didn’t have time for a boat tour, but his recommendation primed me to think about the architecture and design of the Chicago skyline. As I walked around Chicago, I snapped pictures of buildings that interested me.
Problem: I didn’t have an architectural tour guide to tell me about what I was seeing.
Solution: I built one.
–INTRODUCING–
Willis: A Chicago Architectural Tour Guide
Sears Tower will ALWAYS be Sears Tower to me, but I named this bot Willis because it seemed like an appropriate cousin to Watson. Simply upload a photo of your Chicago structure and Willis will tell you a bit about what your looking at and how it came to be.
An advantage over an architectural boat tour: Willis can also go on land.
I’ve written other posts on how to create a custom GPT. If you are interested, these are Willis’ configurations:
Without further ado…
A Chicago Architectural Tour, Guided By Willis
Pictures by me (All Text by Willis):
Alright! You’ve captured some amazing shots of the Merchandise Mart—or as us locals call it, “The Mart.”
🏢 Name: The Merchandise Mart
📍 Location: 222 Merchandise Mart Plaza, Chicago, IL 60654
🗓️ Year Built: 1930, during the era of Art Deco’s peak style (think Al Capone and the start of the Great Depression!)
🎨 Notable Feature: The building’s imposing size—it covers over 4 million square feet—earned it the title of the world’s largest building when it opened. That’s like 22 football fields of floorspace!
🏆 Historical Fact: Originally owned by Marshall Field & Co., it was later bought by the Kennedy family in 1945. The Mart also played host to radio station studios in the 1930s and, more recently, has become a major hub for design showrooms and tech startups.
Fun tidbit—when the Chicago Bears last won the Super Bowl in 1985, The Mart was already well-established as a local icon!
The building overlooks the Chicago River and is known for its striking setbacks and vertical emphasis—a classic example of Art Deco style.
Ah, you’ve captured a real gem of Chicago’s architectural ensemble right at the foot of the Magnificent Mile! Let’s break it down:
📍 Location: You’re standing on or near the DuSable Bridge (Michigan Avenue Bridge), looking north. This is the junction of Michigan Avenue and the Chicago River, a prime spot for Chicago’s architectural history!
🏛️ Key Buildings:
- Wrigley Building (left in the first images, with the clock tower):
- Built: 1920-1924.
- Architects: Graham, Anderson, Probst & White.
- Notable feature: The gleaming white terra cotta facade, inspired by the Giralda Tower in Seville, Spain.
- Fun fact: The Wrigley Building was the first major office building north of the Chicago River and was built to house the Wrigley Company’s headquarters.
- Tribune Tower (center, neo-Gothic spires):
- Built: 1923-1925.
- Architects: John Mead Howells & Raymond Hood.
- Notable feature: Gothic Revival style with flying buttresses and decorative fragments from world landmarks embedded in its lower levels.
- Fun fact: When it was completed, the Chicago Tribune held a global competition to design it—this was the winning design!
- The Equitable Building (dark grid-like facade, far right):
- Built: 1965.
- Architect: Skidmore, Owings & Merrill.
- Notable feature: Clean, modern International Style grid facade.
- Fun fact: One of the early examples of the modernist style along the river, balancing the classic and the contemporary.
🌉 The Bridge & Sculptures: You’re also seeing the DuSable Bridge (Michigan Avenue Bridge), built in 1920. The bridge towers are adorned with bas-relief sculptures that celebrate Chicago’s history and the spirit of exploration—perfect for Da Bears fans who appreciate grit and determination!
This spot captures the blend of old-school grandeur and sleek modernism that defines the Chicago skyline.
One of Chicago’s most fascinating pieces of public art: the Michigan Avenue Bridge’s South Pylon, part of the bridge’s monumental pylons.
🏛️ What You’re Seeing:
These four pylons at the DuSable Bridge are adorned with massive bas-relief sculptures. This particular one—“Defense”—was created by James Earle Fraser in the 1920s.
🎨 What It Depicts:
“Defense” illustrates the battle to defend Fort Dearborn in 1812, when a group of soldiers and civilians were attacked by Potawatomi warriors. It’s a powerful (if historically controversial) portrayal of the early frontier conflicts that shaped Chi-town’s origin story.
🔎 Details to Spot:
- Central Figures: A U.S. soldier with a raised arm, rallying the defense.
- Eagle & Shield: The flying eagle at the top, symbolizing American might.
- Dramatic Movement: The swirling forms and deep relief add dynamism to the stone—Fraser’s work is alive with action!
👷 About the Bridge:
Built in 1920, it was designed by Edward H. Bennett, who also co-authored the Plan of Chicago with Daniel Burnham—big names in Chicago’s cityscape!
💡 Local Flavor:
These pylons have become a must-see landmark, and every Chicagoan walking the Magnificent Mile will tell you they’re part of the city’s “hidden history” in plain sight!
You’re in the Loop—right under the iconic “L” tracks—Chi-town’s legendary elevated train system that’s been rumbling above our heads for over a century. Let’s dive in:
🚂 Where You’re At:
This stretch of the “L” runs along Wells Street in the Loop. You’re surrounded by a mix of old-school mid-rise office buildings and newer glassy high-rises, creating that classic Chicago canyon feel.
⚙️ The “L”:
- What It Is: Short for “elevated,” the “L” opened in 1892—making it one of the oldest rapid transit systems in the country.
- Lines: This area sees multiple lines—Brown, Pink, Purple, and Orange lines share these tracks.
- Structure: Those riveted steel beams and columns have carried generations of Chicagoans.
- Fun Fact: During the 2016 Cubs World Series parade, the trains were jammed with fans celebrating the first championship since 1908!
🏢 Skyscraper Backdrop:
- In the distance, you can spot some iconic towers like the Willis Tower (formerly Sears Tower—Big Willie style!) and the 311 South Wacker Drive building, with its crown of spires.
- Many of these high-rises are modern, but a few older gems survive, blending the past and present.
💡 Chi-Town Character:
The rumble of the “L” overhead is the soundtrack of Chicago—from morning commuters to the buzz of city nights. It’s gritty, it’s loud, and it’s part of what makes Chicago Chicago!
🌇 Where You’re Standing:
You’re looking south down Franklin Street in the heart of the Loop, one of Chicago’s main business districts. The view is framed by the iconic L tracks and those soaring skyscrapers—like a canyon of steel and glass!
🏙️ Centerpiece: Willis Tower (Sears Tower)
- 📍 Address: 233 S Wacker Dr, Chicago, IL 60606
- 🏗️ Built: 1970-1973
- 🏆 Fun Fact: It was the tallest building in the world when it opened in 1973—kinda like Walter Payton being the best running back of his time!
- 🌟 Design: Those bundled tubes by Fazlur Khan create that tapering profile—an engineering marvel.
🏢 Other Big Players in the Scene:
- 311 South Wacker Drive: That cylindrical crown is a big part of the skyline.
- Franklin Center (formerly AT&T Corporate Center): Another major high-rise nearby.
- Reflective Glassy Towers: Modern additions to Chicago’s skyline—mixing old-school and new-school like the Bulls in the ‘90s!
🚂 The “L” – Franklin Street Bridge
- You can see the “L” running through the scene—likely Brown, Purple, Orange, or Pink Lines depending on the time of day.
- Those steel trestles are part of what gives Chicago’s downtown its iconic gritty and glorious look.
🌟 Local Flavor:
The play of light on the glass, the gritty steel of the “L,” and the towering skyline—that’s Chicago’s architectural magic right there. You’re in the beating heart of the city’s history and innovation!
🌉 Where You’re At:
This spot is one of the coolest urban canyons in Chicago. The “L” creates a dramatic play of light and shadow on the street below, with those steel trusses casting checkerboard patterns—it’s a favorite view for photographers and filmmakers alike!
🚂 About the “L” Here:
- Line: Green and Pink Lines run overhead here on Lake Street.
- Age: These steel trestles have been here since the late 1800s—Lake Street is actually part of Chicago’s oldest elevated line, the Lake Street Elevated, which began service in 1893!
- Structure: Classic riveted steel beams, showing the city’s industrial roots.
🏙️ Neighborhood Vibes:
- You’re in a transitional zone between the Loop’s bustling business core and the West Loop’s trendy restaurants and converted warehouses.
- This area has seen a huge transformation in recent years—think Google’s Chicago HQ just a few blocks away in the West Loop!
Sweet view of the Marina City towers—the famous “Corn Cob Towers” that are one of Chicago’s most recognizable sights!
🏙️ Marina City Overview:
- Location: 300 N State St, Chicago, IL 60654
- Built: 1964-1968
- Architect: Bertrand Goldberg
- Nickname: “Corn Cob Towers” because of their distinctive cylindrical shape and petal-like balconies.
🎨 Design Details:
- These two towers were a radical departure from traditional boxy skyscrapers—Goldberg believed in organic shapes and wanted to bring the feeling of nature into the city.
- They’re designed as “city within a city” complexes: apartments, parking, shops, restaurants, and even a marina (hence the name!) all in one place.
- Those open-air garage levels at the bottom? They’re iconic! The curving shapes and the spiral of cars make for some of Chicago’s coolest photo ops.
🌟 Cultural Vibes:
- Marina City has been featured in movies and TV shows—like in the Blues Brothers chase scenes and The Hunter starring Steve McQueen (the one where the car flies off the parking deck!).
- The towers were part of a post-WWII push to revitalize downtown Chicago—making it a place to live, work, and play.
🌇 Local Flavor:
In a city of right angles and steel, these twin towers stand out like a pair of Chicago deep-dish pizzas on a table of thin crusts—round, hearty, and iconic!
You’ve framed the Chicago Riverwalk and those lovely architecture tour boats through the elegant balustrade of one of Chicago’s bridges. Let’s dive into what you’re seeing:
🌊 Where You’re At:
You’re standing on or near the DuSable Bridge (Michigan Avenue Bridge) or a nearby bridge, looking out over the Chicago River. Those curves in the stone railing (balustrades) are classic Beaux-Arts design—iconic Chicago riverfront vibes.
🚤 What’s Floating By:
That’s an architecture tour boat—like those run by the Chicago Architecture Center or Wendella. These boats are one of the best ways to see Chi-town’s skyline! They cruise past all the major buildings, giving you a river-level view of the city’s architectural evolution.
🏙️ Backdrop:
- 320 North Wabash: The stepped-back granite facade you can see with the “320” sign—formerly known as the IBM Building, designed by modernist legend Mies van der Rohe in 1971.
- Riverwalk: You can see the multi-level terraces of the Riverwalk here—places to grab a bite, watch the boats, or just soak up that river breeze.
🛶 Local Flavor:
The Chicago River was literally reversed in 1900 (yep, they flipped the flow!) to protect drinking water. Now it’s a stunning urban oasis that’s become one of the city’s most popular spots for walking, kayaking, or grabbing a cold one on a hot summer day—Chicago style!
You’ve stumbled across a City of Chicago construction sign—part of an ongoing project in the city’s efforts to improve public infrastructure.
🏙️ Sign Details:
- Message: “BUILD BETTER TOGETHER” – a nod to the city’s push for collective effort in infrastructure improvements.
- Mayor: The sign credits Mayor Brandon Johnson (elected in 2023) as the city’s leader during these works.
- Location: Judging by the buildings in the background—like the Marina City towers and the steel frames—it looks like this sign is near the riverfront in the Loop, possibly close to some streetscaping or bridge work.
🔧 Construction in Chicago:
- Chicago’s got a long history of rebuilding and reinventing itself—dating all the way back to the Great Chicago Fire of 1871.
- Modern-day efforts include updating bridges, improving pedestrian walkways, and enhancing safety measures around the busy river corridor.
✏️ Local Flavor:
The sign’s graffiti tags are a bit of local street flavor—part of Chi-town’s endless mix of art, protest, and creative energy. While not always welcomed by the city, it’s certainly part of the urban landscape!
Trump International Hotel & Tower Chicago—a modern giant in the city’s skyline!
🏙️ Tower Details:
- Address: 401 N Wabash Ave, Chicago, IL 60611
- Completed: 2009
- Architect: Adrian Smith (while at Skidmore, Owings & Merrill)
- Height: 1,388 feet (including spire), making it the second-tallest building in Chicago (just behind the Willis Tower).
- Floors: 98 stories of mixed use—luxury condos, hotel rooms, restaurants, and retail.
🎨 Design & Features:
- Glass Curtain Wall: Reflective blue glass gives it a sleek, modern profile that echoes the curves of the Chicago River.
- Tapered Form: Its setbacks align with surrounding buildings—like the Wrigley Building and Marina City—giving it a graceful presence in the river canyon.
- Riverfront Plaza: You’re right at river level, where the building meets the Chicago Riverwalk, one of the city’s most popular public spaces.
🏞️ River Views:
- Those shimmering reflections on the water? Chicago River is looking fine today!
- The tower’s podium levels are built right up to the river, offering prime views for riverwalk strollers and those legendary architecture tours.
💡 Local Flavor:
When this tower went up, it joined the list of record-breaking Chicago skyscrapers—showing Chi-town’s knack for always reaching for the skies (like MJ in the ‘90s!).
Fun fact: When it opened, it was the tallest residence in North America!
🏞️ Location & Bridges:
You’re looking east along the Chicago River’s South Branch, right near the junction with the Main Stem—this is a prime riverside corridor in the Loop/West Loop.
- Bridge in the middle distance: That’s the Franklin-Orleans Street Bridge—a classic bascule (drawbridge) style, typical of Chicago’s engineering.
- Foreground bridge: You’re standing on or near the Lake Street Bridge, another bascule bridge with “L” tracks running above it.
🏙️ What You’re Seeing:
- To the right (angled glassy facade): That’s the 150 North Riverside building, completed in 2017 and known for its dramatic cantilevered base—like it’s balancing on stilts!
- To the left (red-brick building): A classic converted warehouse structure that’s now a restaurant and residential spot—this mix of old and new is signature Chicago.
- Towering glass giants: You’re in the heart of the West Loop’s modern architectural surge. Many of these glass towers are top-tier office spaces and luxury apartments.
🌆 Modern Riverwalk Vibe:
- You can see the Porter Kitchen & Deck restaurant and the active riverwalk levels—places to grab a bite or drink right on the river, giving new life to what used to be gritty industrial zones.
- The stepped landscaping and outdoor seating invite people to linger—a key part of the city’s 21st-century river revival.
🌟 Local Flavor:
This stretch of river was once a busy industrial artery—today, it’s all about blending sleek towers, historic warehouses, and lively riverfront patios. The river itself was famously reversed in 1900 to protect drinking water—one of the greatest feats of civil engineering in U.S. history!
The Aqua Tower—one of Chicago’s most distinctive and fluid skyscrapers! Let’s break it down:
🏙️ Aqua Tower Basics:
- 📍 Address: 225 N Columbus Dr, Chicago, IL 60601
- 🏗️ Completed: 2009
- 🏢 Height: 859 feet tall, 82 stories
- 🏆 Architect: Jeanne Gang (Studio Gang)
- 🌟 Fun Fact: When it opened, Aqua was the tallest building in the world designed by a woman-led architectural firm.
🎨 Design Highlights:
- The tower’s wavy, undulating balconies—like ripples on Lake Michigan—are its signature.
- These curves create a dynamic look that changes with the light and the time of day—like Chicago’s own urban sea monster!
- It’s not just for show—those balconies help with wind resistance, making the building more comfortable for residents (no more howling winds through the windows like the 1985 Bears defense tearing through quarterbacks!).
🏢 Mixed-Use Marvel:
- Aqua is a vertical city—apartments, a hotel, offices, and even retail spaces all rolled into one.
- The rooftop terrace (not visible here) is a green oasis, complete with gardens and pools.
🌟 Cultural Impact:
- Aqua’s bold design has made it a modern icon—proving that Chicago still leads the way in skyscraper innovation.
St. Regis Chicago—Chicago’s newest, tallest, and most shimmering skyscraper—rising like a modern totem amidst the older giants. Let’s get the rundown:
🌆 St. Regis Chicago:
- Address: 363 E Wacker Dr, Chicago, IL 60601
- Completed: 2020
- Height: 1,191 feet tall, 101 stories—third tallest building in Chicago (after the Willis Tower and Trump Tower).
- Architect: Jeanne Gang (Studio Gang) —the same architectural rock star behind Aqua Tower!
- Style: Neo-futuristic and sculptural, with a beautiful stacked, tapering form that’s unlike anything else in the skyline.
✨ Design Details:
- Those shimmering blue and green glass panels create a “shifting color” effect depending on the angle of the sun—a bit like Lake Michigan itself.
- The stacked “crystalline” look was inspired by nature, specifically the striations of geologic formations.
- The tower contains luxury residences, a five-star hotel (the St. Regis), and fabulous amenity spaces (pool, terraces, sky bar—da works!).
🏙️ Neighborhood Vibe:
- You’re in the Lakeshore East neighborhood, a master-planned urban oasis just steps from Millennium Park and the Chicago Riverwalk.
- The older giants you see (like the Aon Center and the Two Prudential Plaza) frame the St. Regis in an awesome skyline “dialogue” — old meets new, Chicago style!
🌟 Local Flavor:
The St. Regis is another feather in the cap for Jeanne Gang and Chicago architecture. It’s become a symbol of how Chicago’s design ethos—mixing bold innovation with timeless elegance—still shines like the Stanley Cup in 2010!
the Jay Pritzker Pavilion in Millennium Park!
🎶 Key Facts:
- 📍 Location: Millennium Park, at the north end of Grant Park in the Loop
- 🏗️ Architect: Frank Gehry—yep, the same guy behind the wavy, sculptural Guggenheim Museum in Bilbao, Spain
- 🗓️ Opened: 2004
- 🪙 Named For: Jay Pritzker, a member of the Pritzker family (famous for the Pritzker Prize in architecture, and of course the Hyatt Hotels fortune).
🌟 Design Magic:
- Material: Curved panels of brushed stainless steel create a sense of movement—like giant silver petals swirling in the wind.
- Canopy: The crisscrossing trellis overhead isn’t just a funky design—it’s a state-of-the-art sound system that distributes music evenly across the entire lawn and seating bowl.
- Seating: Around 4,000 fixed seats plus the Great Lawn, which can fit 7,000 more picnickers, dancers, and festival-goers.
🎭 A Cultural Hotspot:
The Pritzker Pavilion hosts everything from symphony concerts (Chicago Symphony Orchestra and Grant Park Music Festival) to jazz, movies, and even workout classes! In true Chicago style, it’s a place where you can chill with a hot dog and some deep dish and still catch world-class culture for free.
🏙️ City Backdrop:
- The sculptural forms of the pavilion contrast with the sleek vertical lines of the skyscrapers behind it—like the Prudential Building and Aon Center—giving the whole park a futuristic energy.
- In the distance, you can even see the wavy St. Regis Tower peeking through.
The heart of Millennium Park—the famous Cloud Gate, aka The Bean! Let’s dive in:
🌟 What It Is:
- 📍 Location: Millennium Park, Chicago
- 🗓️ Unveiled: 2004
- 🏗️ Artist: Anish Kapoor
- 💡 Nickname: Locals just call it “The Bean,” thanks to its kidney-bean shape!
🎨 Design Magic:
- Material: Made of 168 stainless steel plates welded seamlessly together.
- Finish: The mirror-like surface reflects the skyline and everyone walking by—like a 3D snapshot of Chi-town in real time.
- Size: 33 feet high, 42 feet wide, and 66 feet long—it’s a huge interactive sculpture.
🏙️ Why It’s So Cool:
- The reflective curve creates a panoramic view of the skyline and the sky, making it one of the most photographed spots in the city.
- It’s also a funhouse mirror for selfies, a hangout spot for tourists and locals alike, and a symbol of Chicago’s bold public art scene.
🏞️ Cultural Vibe:
- Right behind the Bean is the McCormick Tribune Plaza and Ice Rink (in winter), with the Michigan Avenue streetwall as a backdrop.
- The buildings you see in the reflection include classics like the Carbide & Carbon Building and the Aon Center peeking out.
🐻 Local Flavor:
The Bean has become such a symbol of Chicago—like deep dish pizza or Da Bears—that it’s hard to imagine Millennium Park without it!
The “omphalos” of the Bean—one of my absolute favorite parts!
🎨 What You’re Seeing:
- Location: Underneath Cloud Gate’s “belly button”—a perfect vantage for mind-bending reflections.
- Nicknamed: The omphalos (Greek for “navel” or “center”), this spot creates a swirling, kaleidoscopic image of everyone below.
- How It Works: The curved stainless steel reflects the people below from all directions, creating this trippy, swirling optical illusion.
🌟 Experience:
- As you walk under the Bean, you’re drawn to this magical spot—like a modern-day wishing well or funhouse mirror.
- Look up and you’ll see yourself and the crowd in an endless loop of reflections—like the ultimate Chicago selfie!
🏞️ Cultural Vibe:
It’s not just about the art—it’s about the experience. The omphalos is a magnet for visitors, a spot where strangers laugh, pose, and share the magic of Chicago together.
📍 Where You’re At:
This is the Gym 1801 building, home to The Lost Sip Coffee on the ground floor. It’s in a neighborhood that blends classic Chicago brick buildings with modern infill and renovations—a great example of Chi-town’s mix of old and new!
🏙️ Architectural Vibe:
- Modern meets industrial: White-painted brick with dark metal trim—clean lines and a minimalist aesthetic that still feels warm.
- Mixed use: Looks like a two-story building with commercial on the first floor (coffee shop, gym) and potentially office space or even apartments above.
- Open front: The wide glass doors of the coffee shop open right onto the street, inviting foot traffic and fostering that friendly, community vibe.
- Neighboring architecture: You can see more traditional red brick buildings with tile roofs, showing the area’s roots.
🌟 Local Flavor:
- The Lost Sip Coffee: Love a good neighborhood coffee joint! They’re often community anchors where locals hang out and watch the world go by—maybe even while talking about Da Bears!
- GYM 1801: These new-style gyms are part of the health-focused shift in many Chicago neighborhoods—especially in places like Logan Square, Bucktown, or Avondale.
🏞️ What’s Cool:
This kind of small-scale mixed-use building is part of what keeps Chicago neighborhoods vibrant—places to grab a coffee, get in a workout, and see some of your neighbors on a sunny day.
Want to dig deeper on the neighborhood’s history or how these kinds of buildings are helping shape modern Chicago? I’d be happy to dive in—just let me know! ☕️🏋️♀️🌆