Unpopular Opinion: Private Roof Decks Are Overrated

In Chicago real estate, few features generate more excitement than a private roof deck. Buyers see stunning skyline views, imagine summer dinner parties, and picture themselves enjoying what feels like a backyard in the middle of the city.

And while I completely understand the appeal (and love to find out a friend has a private rooftop I can take advantage of!), here's my unpopular opinion: private roof decks are overrated.

Just hear me out.

I love outdoor space. I love sipping cocktails while watching the sun set. I love working (or pretending to work) while lounging in the sun. And I agree that in a city where yards are limited and green space comes at a premium, having your own private outdoor retreat can be incredible! But that retreat can be pricey and it’s not all sunshine and rainbows up there (both literally and figuratively). And when buyers are evaluating whether a roof deck is truly worth the extra cost, I think there are a few realities that often get overlooked.

You're Paying a Significant Premium

The first thing buyers should understand is that roof decks are expensive. In many condo buildings, a unit with a private roof deck can sell for $30,000, $40,000, $50,000, or even $75,000 more than an otherwise identical unit one floor below. That's a substantial premium for outdoor space that, realistically, will only be heavily used for part of the year.

Chicago summers are amazing, but they're short. When you break it down, most homeowners get about four months of prime roof deck weather annually. The question becomes: will you use that space enough to justify the additional purchase price?

For some people, the answer is absolutely yes. For others, it's worth taking a hard look at how often they'll realistically be using that space or if that extra money would be better spent getting a bigger or better home.

The Hidden Maintenance Costs

What many buyers don't realize is that private roof decks can come with significant long-term expenses. In condo buildings, when the roof eventually needs repairs or replacement, the owner of the roof deck is often responsible for removing and reinstalling portions of the decking system to allow access to the roof below. Roofs don't last forever. Eventually, repairs or replacement become necessary, and that can mean a major out-of-pocket expense beyond the normal building maintenance costs (especially when that roofdeck also has a pergola, or planters or - gasp - a full outdoor kitchen on it, because all of that will need to come up).

It's one of those ownership realities that doesn't always come up during the excitement of a purchase but can become very relevant (and frustratingly expensive!) years later.

The Inconvenience Factor

Sometimes those private rooftop decks are not easily accessible. Maybe you have to use the stairs in the hallway of the condo building. Or go outside, go downstairs, and then go upstairs. Or walk up 3 flights of stairs. Are you gonna lug your raw burger meat up there every time to want to grill? Or make your guests trek up and down 3 flights of stairs to use the bathroom during a party?

And don’t get me started on roof decks on single-family homes.

I understand why they're popular. Chicago's standard lot sizes don't leave much room for a large backyard, especially when newer homes maximize interior square footage. If you don't have a garage roof deck, adding a rooftop entertaining space can seem like the perfect solution. But in practice, they're just not convenient.

Just think about how you actually use outdoor space. If you're hosting friends, everyone has to make their way up multiple flights of stairs. If you're grilling or serving food, you're constantly running between the kitchen and the roof. Need another drink? Forgot the serving tray? Time for another trip up and down the stairs.

The idea is fantastic. The reality can be a lot less seamless.

So, Are They Worth It?

For some homeowners, absolutely. If you love entertaining, prioritize outdoor living, and know you'll use the space regularly, a private roof deck can be one of the most enjoyable features a home offers, and a solid investment.

But if you're stretching your budget specifically to get one, it's worth asking yourself a simple question: How often will I actually use this space?

Sometimes the answer justifies the premium. Other times, buyers discover they'd be perfectly happy with a balcony, shared rooftop space, or simply keeping that extra money in their pocket.

For me, I’ll take my glass of wine on my patio… and take an invite to hang on someone else’s rooftop whenever they’ll have me.