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I bought a nearly 100-year-old skyscraper in Chicago and want to preserve its identity while making a few changes. Here’s what I plan to do.

July 1, 2025
in News
I bought a nearly 100-year-old skyscraper in Chicago and want to preserve its identity while making a few changes. Here’s what I plan to do.
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A man on top of a skyscraper in Chicago.
Tom Liravongsa atop the Pittsfield Building in Chicago.

Skyscraper Media

This as-told-to essay is based on a conversation with Tom Liravongsa, or Tom the Skyscraper Guy, a real estate investor who purchased the majority of the Pittsfield Building, a 38-story skyscraper in Chicago that has been partially vacant for nearly a decade. Liravongsa is turning the former office building into residences. The building was built in 1927 and landmarked in 2002. The conversations have been edited for length and clarity.

This building has quite a history.

It’s been in disarray for over a decade, and if you dive into the real history of it, it’s gone through so much turmoil.

We knew that it was a Marshall Field estate building. It was built by Marshall Fields III, and prior to it becoming a disarray, I think the last lease burned in 2017. Prior to that, it was the largest medical office east of the Mississippi with 775 doctors and dentists in the building.

The copper top of a skyscraper in Chicago.
The Pittsfield Building was built in 1927.

Skyscraper Media

It’s also in Jewelers Row, which is a really prominent area for selling high-end jewelry. In fact, we discovered recently that on the sixth floor, there’s a store that sold pearl jewelry.

All of the remnants that we’ve just been discovering, you wouldn’t have found them unless you were in the building. There are safes that were built into the wall and compressors in the basement specifically for compressed air for doctors and dentists to use.

There are grotesques on the corners of the building. I didn’t even know they were there until we were literally hanging over the building.

It’s really unique.

I bought 80% of the building for about $7 million

Shortly after COVID, I was looking at basically all markets that had office spaces, knowing that there would be a shift in how office space is used.

Not only is the Midwest close to home, but I’m very familiar with Chicago. I’ve been here long enough to know Chicago is also a developer-friendly city when you’re doing the right things, which is residential.

That’s what we’re doing. We’re changing an office building into a residential building, and there are a lot of things that come along with doing something like that.

We acquired the building in May 2023. We had actually purchased it out of a foreclosure, so that’s how we were able to do that.

A man standing on a scissor lift beneath a chandelier.
Liravongsa owns 80% of the building.

Skyscraper Media

We paid just over $7.5 million for it.

We own 80% of the building now. When I say we, yes, it’s investors, and the investors are your partners. Most people would be familiar with something like New York City, where they have vertically bifurcated buildings — that’s the same situation that you have here in Chicago. So, we own everything except floors 13 to 21.

All of it was office space. I believe they started doing conversions in 2009. The building currently has 228 apartments, which are about 80% full.

Those are active market-rate apartments that are located on floors 10 to 21. We have three floors of apartments, and the floors we don’t own are all apartments.

A man sitting on top of a skyscraper in Chicago.
The Pittsfield Building has 38 floors.

Skyscraper Media

The rest is now just completely vacant. And that’s what we are working through and getting turned into apartments.

It will still have some mixed-use, meaning we’ll have retail-floor activation, and we’ll have basement activation.

More importantly, for 100 years, people have not been able to see this building for what it is — this craftsmanship specifically. They’ve not been able to see things such as the copper top.

So we’re offering a lot of this viewing to the public, like a museum inside the building.

I want to take advantage of the classic craftsmanship

Most developers come in and they just want to make it their own — and their own is going with what they think the market is, which is like a glass tower. We’re building glass towers now, and they’re nowhere near the attention and the allure that this building has.

There’s been a real shift in the market to what we call themed buildings because these conversions are happening, and a themed building — like this 1920s craftsmanship building — has its own allure outside being a glass tower. Anybody can go and live in a glass tower; there’s nothing exciting about that.

But to have this building with all of these features and to be able to reference them, there’s something to be said about it.

To modernize different components, you’ll have amenity spaces that will be a mixture of modern and also maintain a lot of the craftsmanship.

A man holding a light standing in an elevator lobby.
The building is landmarked, and Liravongsa wants to keep its 1920s charm.

Skyscraper Media

The hallways and other areas will be very much maintained, but some of the interior units might be a little more modern. But when we talk about modern, we’re thinking about the basics: the way your doors and windows work.

We’re talking about how HVAC and other systems are going to be modernized. Those are basic modernizations, but you can still incorporate those behind walls so you can keep the allure of these older buildings without having to change them per se.

The state of the commercial real estate market right now is that there is empty office space. We were just introduced to another WeWork-style space, completely empty — six floors of it. We were thinking, “Oh, this is such a sad thing.” I remember a time when I thought, I would love to be in an office like this. Now there’s no one in those offices. And so the question is, what do we do with those?

We knew that this was a maximized residential building. But more importantly, Chicago has one of the best job markets in the Midwest. It’s a hub, but there are also a lot of people who live here. You don’t need an office right now; we need housing.

The post I bought a nearly 100-year-old skyscraper in Chicago and want to preserve its identity while making a few changes. Here’s what I plan to do. appeared first on Business Insider.

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