Chicago has a weird relationship with its old buildings. We either tear them down to build glass boxes or we hug the brick so tight it becomes a personality trait. 111 N Canal St is different. It’s not just a "cool loft office" in the West Loop; it’s basically the epicenter of how Chicago transitioned from a rail-and-rust city to a global tech player. You've probably seen it—the massive, hulking structure right by the Ogilvie Transportation Center. It’s called Gogo Plaza now, mostly because of the giant signs, but its history is way more interesting than just a corporate headquarters.
It wasn't always a tech sanctuary.
Originally, this was the Butler Brothers Warehouse. Think about that. Back in the early 1900s, this wasn't where people sat with MacBooks sipping $7 lattes. It was a gritty, high-functioning storage facility for a massive mail-order company. The floors are thick. The columns are huge. It was built to hold literal tons of physical goods. That’s actually why it’s so popular today. Modern tech companies need heavy floor loads for data infrastructure, and they want the high ceilings because, honestly, who wants to work in a cubicle with a 8-foot drop ceiling anymore?
Why 111 N Canal St became the West Loop's "It" building
Location is the obvious answer, but it's deeper than that. You’re steps from the Metra. That matters. If you’re a CEO trying to hire the best engineers from the suburbs and the best creatives from Wicker Park, you need to be at the nexus. Sterling Bay, the developers who basically reimagined the modern Chicago skyline, saw this coming a mile away. They bought the building in 2012 for about $100 million. At the time, the West Loop was still "emerging." Now? It’s the most expensive dirt in the city.
The renovation was massive. They didn't just paint the walls. They ripped out the guts and replaced them with high-speed fiber, modern HVAC, and amenities that make most apartments look like closets.
The Tenant Mix is a Who’s Who of Innovation
When you walk into the lobby, you aren't just seeing one company. You’re seeing a microcosm of the Chicago economy.
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- Gogo: The in-flight internet giants. They took a massive chunk of space and put their name on the top.
- Uber: Before they moved over to the Old Post Office, they had a significant footprint here.
- Potbelly Sandwich Works: Their corporate HQ is tucked in here too.
- SAP Fieldglass: A major player in the cloud software space.
It’s a weird mix. You have sandwich executives walking past guys coding the next generation of satellite wifi. But that's the point. 111 N Canal St was designed to foster that "accidental" networking. The roof deck is a prime example. It’s not just a patch of grass; it’s a full-blown lounge with views that make you realize why Chicago is the best architectural city in the world.
The Sterling Bay Effect and the $290 Million Payday
Business is about timing. Sterling Bay is the king of timing. After pouring money into the renovation and filling the building with high-value tech tenants, they sold it in 2015.
The buyer? J.P. Morgan Asset Management.
The price? $304 million.
That is a staggering return on investment in just a few years. It proved that the "tech-loft" concept wasn't just a fad for startups; it was institutional-grade real estate. When J.P. Morgan cuts a check that big, it signals to the rest of the global market that the West Loop is a safe bet. It paved the way for Google moving into the old cold storage building down the street and McDonald’s bringing their HQ back to the city.
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What most people get wrong about the architecture
People call these "loft" buildings, but 111 N Canal St is actually a "Chicago School" influenced industrial structure. Designed by Daniel Burnham's firm—yes, that Burnham—it has a pedigree that most modern buildings can't touch.
It’s built with a reinforced concrete frame. This is crucial. Most of the old timber-frame lofts in the city have fire safety issues or floor-load limits. Not this place. You could probably park a tank on the fifth floor and the building wouldn't flinch. This structural integrity allowed for the "open plan" office craze to actually work. You don't need a million tiny support walls when you have the skeletal strength of a Burnham-designed warehouse.
Modern Amenities in a 100-Year-Old Shell
Let’s talk about the gym. It’s called the "Canal Street Fitness" center, and it’s better than your local Equinox. Seriously. Then there’s the bike room. In a city like Chicago, where the train is great but biking is better (in the summer, anyway), having a secure place to put your ride is a dealbreaker for talent.
- The Rooftop: It’s a 15,000-square-foot outdoor space.
- The Lobby: It feels more like a hotel than an office building. There’s a fireplace. There’s high-end art.
- The Transit: You are literally on top of the Ogilvie Transportation Center. If it rains, you can get from your desk to your train seat without getting a drop on your head.
The Reality of Working at 111 N Canal St
Is it all sunshine and venture capital? Mostly. But there are quirks. Because it’s right by the tracks, you’re going to hear the city. It’s loud. It’s vibrating. It’s Chicago. If you want a silent, sterile suburban office park, this isn't it.
The elevators can be a bit of a wait during the morning rush. That’s the price you pay for a building that was originally designed to move freight, not 4,000 humans all at the same time. But honestly, the energy in the building is infectious. You feel like you're in the middle of where things are actually happening.
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The West Loop neighborhood itself has changed around the building. When Butler Brothers were there, the area was full of meatpackers and wholesalers. Now, you have Au Cheval down the street (good luck with the three-hour wait for a burger) and Gibson’s Italia right across the river. You’re in the culinary heart of the Midwest.
Why it still matters in 2026
The "office is dead" narrative has been beaten to death. But buildings like 111 N Canal St prove that great offices aren't dead. Generic, boring offices are dead. High-ceilinged, amenity-rich, transit-connected hubs with historical soul? Those are still at 90%+ occupancy.
Companies are downsizing their total square footage but upgrading the quality of the space they keep. They want a "flight to quality." They want a place that actually makes employees want to leave their couch. This building is the blueprint for that. It’s why companies like Vivid Seats and Ferrara Candy have looked at this corridor for their flagship spaces.
Real Estate Specifics for the Nerds
- Total Square Footage: Roughly 860,000 square feet.
- Floor Plates: Massive. We're talking 50,000 to 80,000 square feet per floor. This is a dream for big tech firms that want everyone on one level.
- Sustainability: It’s LEED Gold certified. Taking an old warehouse and making it green is way harder than building a green building from scratch.
Actionable Insights for Businesses and Investors
If you're looking at 111 N Canal St—whether as a potential tenant, an investor, or just a fan of Chicago's evolution—keep these things in mind:
- Prioritize Transit-Adjacent Assets: The value of this building is 50% architecture and 50% its proximity to the Metra. In a hybrid-work world, the "commute friction" must be zero.
- Character Over Chrome: Modern glass towers are everywhere. But you can't fake the history of a 1918 warehouse. Employees, especially younger ones, gravitate toward spaces that feel "authentic."
- Adaptive Reuse is the Future: If you're an investor, look for buildings with high floor-load capacities and high ceilings. Those are the only two things you can't "renovate" into a building later.
- The Amenity Arms Race: If your building doesn't have a rooftop or a world-class gym, you're losing. 111 N Canal set the bar for what "office amenities" actually mean. It’s not just a coffee machine anymore.
111 N Canal St isn't just a street address. It’s a case study in how to respect the past while absolutely dominating the future of the workplace. It’s gritty, it’s expensive, and it’s undeniably Chicago. Whether you’re there for a meeting at Gogo or just passing by on the way to the train, it’s worth a second look. It’s the building that taught the West Loop how to be cool.