I would probablt enlarge that front bed and have nice foundation plantings there and move the boxwoods to mor eappropraite space like along the walkway . Bring the bed forwad to line up with the edge of that walkway right in front of the door . The bed then could have a space behind for the reasons mentioned but have some interesting plants that give you all the things you want . IMO anything planted in front of the boxwoods will end up not being able to see them . I often do evergreens and perennials in a large bed then add some annuals for that long lasting color you want .

What they said about not planting behind the boxwoods. Absolutely not. Use the advice you’ve paid for.

Extend your beds further into the yard and plant some attractive low blooming perennials in front.

Does your municipality have code on this? I know not all of Chicagoland has the same codes. Most of it is pretty basic, and I would hope your landscaper knows what it is where you are. I'm not sure what you mean by retaining wall since you don't seem to have one. But if you have one somewhere, you probably want to make sure it's in code when you rebuild it.

Don't plant behind the boxwoods. They are already real close to the building, you do not want to cram anything else close to the building.

Thanks, everyone, for the fantastic suggestions!! Our plan is to extend our flower beds further into the yard so they line up with the edge of the walkway in front of the door.

Do you have any suggestions for the flower bed border? I was thinking about stone/brick, but I am not sure about the color or design.

Also, any suggestions for specific plants to complement the boxwoods, besides hydrangeas, and where to position them?

Don't do a hard boarder. Edge the grass with a spade or edging tool. It is a classic look. If you move the boxwood out then you can add a hydrangea or two. How about mountain laurel and rhododendron. Front with a few perennials like hostas and lambsear and annuals for season long color. Prune the bush to the right of the door.

If you could find brick to match your house, that would be awesome! Otherwise, maybe a stone in a beige-y tone would blend well.

Hydrangeas are much too large for in front of the boxwoods. And which direction does your house face? How many hours of direct sun exposure makes a huge difference.

Some 2 foot tall blooming easy-care perennials that would work in Chicago are yarrow, ajuga, columbines, valerian, Shasta daisy, coreopsis, blanket flower, coneflower, daylily, candytuft, lavender, daffodil, primrose, aster, poppy, verbena, periwinkle, and many more.

edited to add - if you’re simply dying for hydrangeas, you could have the boxwoods ripped out and plant some of the SMALLER VARIETY of hydrangeas, at least 4’ from the house. Like Little Lime or Bobo variety. Unless your house faces west or south because hydrangeas might roast in those conditions.

The reality is that you are trying to do a lot in a very small space. And that the height of what you can do is limited by how close to the ground the window is. So you can't go closer the the house than the boxwood are now, and you can't go much taller than the boxwood.

I'd just plan on pulling the edging, and planting a row of annuals.

Boxwoods can grow quite tall. You could let the one next to your door grow taller.

That said, creeping phlox (phlox subulata) will be pretty closer to evergreen (it tend to become gray and dry in very cold weather when there's no snow cover. Mine is mostly evergreen in zone 6, Maine. Then, you could plant a range of bulbs in the phlox, which would get you a bigger, low-growing garden with lots of flowers in the summer.

I, too, agree that enlarging the bed will be great. I am also in the area and have good luck with native geraniu, Geranium maculatum. It stays green in winter (some leaves get red) and pops in spring. You can buy it from Prairie Nursery in Wisconsin.

I would go wider with plant part

If what you have to the right of your entrance is a climbing Hydrangea, I would either build a trellis for it or move it. I have one (North facing, Zones 6a/6b). It is an aggressive grower on the iron trellis that I had designed for it. I have to regularly trim it all summer long. The branches look lovely in the winter when they are bare. But your plant doesn’t look like it is in the right place if it is, indeed, a climbing hydrangea. Also note…hydrangea do not stay green all year round. They can add color, but their season is short. I always underplant mine with annuals. And, yes…you need to prune boxwood to keep them that height and shape. Yours appear to be appropriately planted. Do not plant anything behind them. Yes to larger, curved beds. And yes to dark mulch vs. stone.

I'm surprised to see your boxwoods looking so healthy. In Toronto they've been going downhill for awhile, but in the last few years the caterpillars of the box tree moth have eaten most of them down to skeletons. Everyone is pulling them out.

You might want to ask your landscaper if your boxwoods are going to be around for awhile, before you make your plan around them. https://www.russelltreeexperts.com/arbor-ed/2023/12/5/10-boxwood-alternatives