Ranking 11 Of The Most Traditional Chicago Building Types From Best To Worst

When you think of Chicago architecture, you probably envision the iconic Chicago skyline, the Tribune Tower, The John Hancock Center, or the buildings up and down Michigan Avenue or Lake Shore Drive. But there is so much more to know about than skyscrapers in downtown Chicago — the neighborhoods are full of unique home styles that you won't find anywhere else.

As a real estate team based in Chicago, we are obsessed with all of the architecture the city has to offer and love to debate our favorites. We know that at the end of the day, the style of home that tops your list comes down to personal preference, but as people who have toured thousands of homes from Lake Michigan to Bucktown and beyond, we thought we’d share our ranking of the most common building types you’ll find in the city.

1. Victorian Queen Anne

The Victorian Queen Anne easily slides into our top spot. I have a soft spot for ornate details and structures that you don't get to see very often in the city, like columns and spires. Usually, you see a lot of these Victorian properties on corner lots because they prioritize bringing in natural light, so that's how these are built. I also love having a front porch. Usually, you’ll find a front and side wraparound porch on a home like this — big fan of 'em. I don't think you can get anything more classic than a spire. Seriously, who doesn't want to have a spire on their house?

2. Chicago Greystone

If you're a real estate person in the city and you see a Chicago Greystone, you immediately put that at or near the top of your favorites list, period. If you choose 10 real estate agents or 10 real estate investors here in Chicago, I would argue that nine of them have a dream of converting a classic Chicago Greystone into a single family. You'll see many of these in neighborhoods like Lincoln Park, the Gold Coast, and Logan Square. It's the top echelon of what real estate people want to do because they are so iconic in the city and simply put, gorgeous. 

3. American Foursquare

The American Foursquare is also landing very high on our list. Why? In Chicago neighborhoods, you primarily see these on wider lots. You have a more square layout, and you get better living space. We're so used to having these long, narrow buildings in Chicago, so these are rare. Like many things in life, the rarer they are, the more valuable, so we rank these very highly. 

4. Chicago Bungalow

I would argue that across the city, from the South side to the North side, this is probably the most common style of home that you’ll see in Chicago neighborhoods. They are everywhere, and people love them and want to live in them for a reason. What I, and many buyers, appreciate about them is they usually have one key notable feature: a huge bay area in the front living room that opens up. They were also one of the first building types to have a side entrance as opposed to the majority of Chicago building types. 

5. Modernist Ranch

Moving on, we have the modernist ranch. I love these. The modernist ranch was made famous by Frank Lloyd Wright. From a visual perspective, they’re both gorgeous and unique. One downside is that many homes like this are built on a smaller scale — doorways narrower, kitchens smaller, etc.  They were so focused on the way things looked and having clean lines, and it’s very apparent when you look more closely at the architecture. A lot of the new construction that you see today borrows elements from this.

6. Workers Cottage

The workers' cottage is a very historic architectural style in Chicago neighborhoods. They built them in droves to support the working class in the city, so there are a ton of them, and they are very standard homes. You see them all the time — the classic homes that you see that they dormer out on the top floor, so they extend the pitch roof line to get more space.

By definition, if you must put an addition on any particular style, that means it wasn't adequate. It may have worked in the 1930s and 1940s for these workmen, but it doesn't always work now. I still think they're cool because they have a great history, but you need to enhance them to make them work for the average person today.

7. Cape Cod

Next up, we have the Cape Cod style home. Personally, I am not a fan of those little dormers that they have — they remind me of little spy houses, and they're primarily for looks, not function. The second floors are always too narrow. You don't have a lot of room to position beds and other furniture. They're very attractive, but they still land at the bottom of my list.

8. Prairie Style Home

Next up, we have the prairie style home. These feel very institutional to me. When I see them, they make me think of a  police station, a  firehouse, or a municipal building, not the people living inside a cozy home. They don’t have amazing windows or layouts — the design is typically focused on the interplay of the exterior look and the interior flow. We find these all over the place, and people are excited about them. Why? Because they're pretty unique here in the city. You won't find them all over the place. So when people walk into a more interesting layout, something that they haven't seen in a long time, they get excited just by virtue of it being a little bit rare. Pretty frankly, I think they miss the mark.

9. Stucco Bungalow

I’ll be honest here —  I hate stucco. It expands and contracts with the heat and cold, which we get large swings between in Chicago. It's also especially gone out of favor in the last 50 years, so it's hard to get quality work. It's one of those things that feels like a sign of the age of a home. People don't choose to build with stucco often at all in this city, so if you see a stucco home, for me, it just triggers issues, issues, and more issues. 

10. Raised Ranch

Now, the raised ranch. I was a general contractor for a very long time and saw a lot of these in my time. You always find a  lower level that they're trying to make feel like a living space, but it's a basement, no matter how much you try to pretend like it's not a basement. The whole house doesn't work well unless you have a true living space or a true dining area, and in these homes, those can easily wind up being in your basement. 

11. Split Level

My least favorite — the split level. You're asking the main level to do too much here. You also typically have really shallow basements. I don’t have much else to say about them because there isn’t very much to describe.

Agree? Disagree? Think I have it all wrong? Watch our full YouTube video on the topic and leave a comment!