ALL plants - except plastic artificial ones - will require periodic routine maintenance to keep them healthy and looking good. Neglect of any kind will result in an ovegrown, unhealthy mess. Even with Sky Pencil hollies!!

Yews are the best shrub for climates with extreme winters. Your yews have been butchered by improper pruning BUT, they can be saved...and it's easy to do. Take more photos and go to a plant nursery for instructions. Be sure to prune them so there is an 18 inch "space" between them and the garden apt. window, it allows for better air flow and easier shrub maintenance. Lived on the South Side for many years in garden apartments...all had yews.

We don't mind a little maintenance. We just want something that doesn't require constant trimming. The barberries in the picture need to be trimmed monthly, sometimes more. The yews are nearly 4 foot tall and just as wide. I'm not sure they can be saved, they are planted less than 18 inches from the windows, and as stated above, they've been butchered. Mostly I'm looking for plants which, similarly to the sky pencil, will keep their shape and rough size without constant maintenance. Trimming in the spring or fall isn't a big deal, just don't want to do it every week or month, we'd put in a lawn otherwise.

LOL!! Yews can be butchered! In fact, they are one of the few conifers that can be cut back to the ground - no green remaining at all - and will regenerate nicely. They also grow slowly enough that pruning only once or twice a year is more than adequate.

And as noted, they are very cold hardy, will tolerate considerable shade and something that will remain fully evergreen even Chicago's freezing winter conditions so great for privacy issues.

There are a great many small compact conifers on the market these days. They are very slow growing and really shouldn't be pruned. The Dwarf Globe Blue Spruce might fit your needs. It would take 30 years to get over grown. It is certainly cold hardy enough for Chicago. You just might need to pay more up front for a bigger one to keep the garden apt. owners happy.

https://plants.monrovia.com/search?w=dwarf%20spruce

https://plants.monrovia.com/search?w=dwarf%20conifers

Although I seldom do, I will disagree with Yard on this point :-) Because they are so amenable to pruning, even very hard pruning, and so slow growing, yews are a excellent choice for this area, even planted 18" away from the wall (if necessary). And there are any number of dwarf or compact forms as well.

I'm not sure how well the Sky Pencil will suit the situation or even fare in your area, but there are certainly other cultivars of Japanese holly that could work. Also boxwood, although I hesitate to recommend that due to the growing prevalence of boxwood blight. And both are slow growing BLE's that will take pruning well.

"My question about the windows is still unanswered."

This is a typical Chicago "8 flat", the windows in question are behind the yews, the sill is about 6 inches above grade.

Back in the day, these yews would have been properly hand-pruned twice per year, keeping the growth back from the window surface about 18 inches. Yews were chosen to give privacy and they hold (most of) the annual snowfall away from the wooden window frame. Sadly, it seems no one wants to take the time to rehabilitate these particular specimens.

"This is a typical Chicago "8 flat", the windows in question are behind the yews, the sill is about 6 inches above grade.

"Back in the day, these yews would have been properly hand-pruned twice per year, keeping the growth back from the window surface about 18 inches."

So there is question whether the yew is planted 18" away, or whether it's growth can be restrained to 18" away. There is a difference and a picture of the exact conditions would answer all the questions. Otherwise, information will be offered based on misunderstandings.

I'd take better pictures but everything is currently buried under ice and snow, which wouldn't provide you much better views.

If the basement windows (in the title) are not visible, then you have to wait.

The basement windows may not be visible until the yews are gone.