This is the story behind ChicagoApartmentBuildings.com: why it exists, what it does today, and what’s coming next for anyone searching for Chicago apartment buildings.
It started with a move to Chicago.
During COVID, I started thinking seriously about moving to Chicago.
The plan was pretty simple: rent an apartment for a year, learn the city, figure out which neighborhoods I liked, and then decide where to buy.
So I started looking for an apartment. And looking. And looking.
I spent hours online and found plenty of apartment listings, beautiful photography, virtual tours and videos of individual units. The problem was that most of those apartments wouldn’t be available by the time I actually moved.
I wasn’t really looking for an apartment yet. I was trying to learn about the buildings: how many were there, where were they, which neighborhoods, how big, which ones allowed dogs, which had pools or rooftops or parking.
I wanted basic information that wouldn’t disappear the moment an apartment got rented. That seemed like a simple request.
“That list is everywhere.”
I had built directories before, so I understood how the information could be organized.
When I started asking around about building a directory of Chicago apartment buildings, I kept hearing some version of the same thing: “That list is everywhere.”
It wasn’t. There were plenty of sites listing apartments for rent, property management sites, apartment search portals, individual building websites.
But I couldn’t find the simple, comprehensive directory of Chicago apartment buildings I’d actually been looking for. That stuck with me.
Then came the dogs.
As we moved into 2023 and my plans for Chicago got more serious, I started researching pet-friendly apartment buildings.
That search turned into my first real attempt at building the resource I’d wanted for myself: a directory of pet-friendly Chicago apartment buildings.
It wasn’t much. The directory was sparse, the information wasn’t nearly as complete as I wanted, and there was a lot more work ahead.
But something interesting happened. People found it, and the interest it got confirmed something I’d suspected from the start: people weren’t only searching for today’s available apartments. They wanted to know about the buildings themselves.
Then AI changed the search.
By 2025, something bigger was happening.
People were starting to ask AI the kinds of questions they used to type into Google: the best apartment buildings in Chicago with a pool, which buildings in Lincoln Park allow big dogs, where to live if you work in the Loop but want to be near the lake.
AI didn’t hand back ten pages of links. It gave a few direct answers.
That changed how I looked at the project. If AI was going to help people decide where to live, it needed good information to work with, and Chicago’s apartment building information was scattered across hundreds of sites, listings, and management companies.
So I decided to build the resource I’d been looking for years earlier, but build it for the way apartment hunting was actually going to work next.
290 Chicago apartment buildings.
Today, ChicagoApartmentBuildings.com is a directory of 290 Chicago apartment buildings across every major neighborhood in the city, with a minimum of 50 units for any new building we add going forward.
The information is organized around the building, not around whichever apartment happens to be available today.
You can browse by neighborhood, location, and amenities, and the underlying data keeps getting researched, checked, and updated.
Next: Ask Joey.
We’re not done. This winter we’re introducing Ask Joey, our Chicago apartment hunting AI bot.
Instead of checking a dozen sites and piecing it together yourself, you’ll be able to tell Joey what you’re looking for and actually have a conversation about it. Maybe that means a dog friendly building in a specific neighborhood with a good pool, EV charging, and a coworking space near the train: the kind of combination that never fits neatly into a row of search filters.
Joey will use the building information we’ve spent years assembling to help point you toward buildings worth considering.
In a way, it brings the whole thing back to where it started. During COVID, I wasn’t looking for a video tour of an apartment that would be rented long before I ever got to Chicago. I just wanted to understand my options.
It took a few years, 290 buildings, and a big shift in how people search, but that’s what we built. Welcome to ChicagoApartmentBuildings.com.