Right here! Is this the space you want ideas for?

yes it is. I would love to use perennials. Live in Chicago area so the pickins are slim.

Have you researched what perennials will survive a Chicago winter? Plant for spring/summer/fall and let snow be your background for winter.

In front of that porch, some low flowering bushes that will hide the underpinning lattice. A tall, skinny Italian plant (an evergreen who's name escapes me at the moment) in the corner will give upward movement.

I'd discard all the various stones, demi-walls and whatver and start with a clean area. It looks like an attempt at terracing that went awry. Terracing is a good idea, but with more definition.

Tulips and hyacinths are bulb that love to get frozen and spring forth. THat's the first phase. When they're gone, you want summer flowers for full (afternoon? morning?) sun -- taller stuff in the back (daylilies, digitalis?) and a variety of shorter stuff in front of them, mixed with caladiums (also bulbs).

Having plants dropped here and yon over that front area isn't working. Pull all that up, and either fill it with English-garden variety of every color that will grow, or create a platform (brick? stone?) for a fountain, (big) sculpture or a smallish tree (Japanese elm?)

To create a really great garden area is the work of several seasons as you learn what works with the amount of time you can devote to it and the weather. Quite a challenge! Good luck!

Roses.

Chicago isn't the Siberian tundra! There are oodles of perennials. Just buy ones suitable for your zone & protect as needed from your infamous cold winds. Get ideas from a multitude of perennial supplier websites--find out your hardiness zone too. Have fun!

When you plant your perennials, I suggest making a place for loads of tulips to surprise you every spring. :)

I lived in NJ, zone 6, I had roses, clematis, hydrangeas, boxwood and other evergreens. I sure there are Home Depot stores near you. If you want a formal garden, plant roses surrounded by boxwood. Try hydrangeas, they are very easy and there are so many varieties, you might have a hard time choosing. Day lily is a great choice also. They bloom at different times of the year, if you choose carefully you could have flowers all the wait into fall.

I live in Chicago also, and there are plenty of perennials that thrive here. It looks like your area is sunny. If so, maybe a butterfly wildlife garden? Coneflowers, black eyed susans, sedum, butterfly weed, goldenrod, and butterfly bush all grow very well here and attract beautiful butterflies. Add a bit of parsley (an annual) for the caterpillars to munch and a small water feature, and you're good to go!

I love those ideas, jguico!

We needed a major overhaul on our front yard a couple years ago and my husband came up with the idea of building a waterfall/fountain. It turned out beautifully and was about 1/10 of the cost since we did it ourselves. It's not quite as cold here as it is in Chicago, but we leave ours running all year long - so pretty when there's snow around it! The pipes don't freeze since the water is continuous.
We also do a mixture of perennials and annuals. Daylily plants are one of our favorites b/c they bloom from late spring until fall and are really hardy (great for hardiness zones 3-10 so should grow in your area too.) Ice plants are also gorgeous for ground covers!

One of the biggest impacts in our yard has been hanging baskets - they're not cheap (we buy three of them every year at $25/ea) but are definitely worth it! If you do this, I'd suggest adding a drip line from your sprinkler system so you don't have to water by hand. Hope that helps!

Here's an "after" picture of our front yard. I'll have to dig up a before picture.

Happy planting! :-)

~Malissa

Oops - sorry! Didn't mean for those pictures to be so big!

We like big photos here at Houzz! Great design!

That's beautiful.

Love your pictures. Your flowers are breathtaking.

Gorgeous water feature meridianmama ! I agree you need a focal point, could be a beautiful fountain or large bubbling water countainer,bird bath or piece of yard sculpure/art. The repeat blooming roses bushes they have now are great too, will need to fill in with annuals a bit for all summer color and a few pots on the porch (though I have learned over the years fewer but larger pots =less watering and repeating the same plant makes more impact than a bunch of different plants in the landscape just be sure to mix up the textures). It is a beautiful house.

You might also consider a mix of small bushes and ornamental grasses or sedges to add structure to your garden with flowers up front. I love the look of cone flowers and others mentioned above but if you haven't lived with them before consider that they self-seed and attract lots of bees. Both of these issues might argue against putting them at your front door -- tough to contain and not welcoming. Also some flowers require lots of deadheading. The fescues, sedges and grasses when massed add color, texture, interest and are much easier to maintain. So then your garden is a pleasure to see and less work for you as a homeowner.

I live in St. Paul, MN. and we have a huge variety of perrenials from which to chose. Chicago is a zone warmer yet, so you should have even more options.

I was glad to see you liked the idea of perennials because that was my first thought. I love perennial gardens and architectural elements. Here are a few ideas (although I don't know which plants grow in your area).
Plant a row of roses below your deck rail across the front, all the same color (I prefer pink and love David Austin roses). They will bloom all summer and add a pretty fragrance as you sit on your deck. Perennials: Pick 3-5 colors you want to use that look pretty together (pink, white, purple, yellow are my favs). Consider height, color, texture and leaf shape as you plant, deciding which look good next to each other. Some things to think about. Draw up a plan. Plant height: work from tall to short, tallest in the back of the bed near the house and shorter plants as borders around the grass. Plant flowers in clumps of 3; it will give you a bigger show of color. Seasons: think spring, summer, fall and pick flowers for each season to have an ever-blooming garden. Add a concrete garden element like a mossy bird bath or a pedestal with a silver reflecting ball. Here are a few plant favorites, if they grow in your area: lavender, daffodils, ground phlox, candytuft, shasta daisies, coreopsis, sweet william, cone flowers, lupines, forget-me-nots, black-eyed susans, foxglove, campanula bellflower, liatris, columbine, delphinium, and hollyhock. You can add a few evergreens if you want, and hydrangeas and bleeding hearts if you have shade. You can check out your local botanical garden for more ideas and plants in your area.
Have fun planting! Would love to see pics when you have it finished.
~ Julie

Even in the Chicago (where we live too) you can grow beautiful, hardy grasses. Try zebra grass, which has a nice varigated green aqbd creaqm color

Go over to Millenium Park if you want to see an amazing display of perennials that thrive in Chicago. I would suggest Nepeta (catmint) spilling over the low retaining walls, A grouping of Prairie dropseed for a midsize native grass, some Knock out shrub roses. Plant in masses, not dots. A small multistem shrub like a Serviceberry would add some height and help frame the porch and give some scale. And, yes, as someone else said, probably loose the retaining walls.

Spend a lovely afternoon at Millenneum Park in downtown Chicago. The Lurie Gardens were designed by the masterful Piet Oudolf. You will find a spectacular variety of perennials that are perfectly suited to your zone. Plus, if you go at different times of the year you will get to see what is in bloom and what plants compliment each other. Good Luck!

I would suggest you leave the back row of plants as they are and fill in the space to the right with large pots of flowering plants you can bring indoors for the winter. If you do not care for this idea, I would suggest pink pampas grass or zebra grass that will remain as a shelter for birds and wildlife over the winter. Then, I would suggest you remove the rocks in front of this curved line of stone and put in a layer of mulch or large patio squares to create a ground-level patio. Next, I would suggest you use black paint on the seat what looks like a white bench that overlooks this space so that the bench will stand out. So that you can see the street or greet guests, you may move the bench to the left side of this small patio and angle it just a bit. As an alternative, you might center it in front of the curved line of stones and add a small lawn chair by each end of the bench.