Landscaping in Chicago is parkway, gangway, clay, and lake wind on a short season. Street trees heave walks and send roots into old laterals. Salt from a long winter burns the same strip of grass every April. Shade from brick three-flats leaves hostas and moss where a catalog wanted sun. Downspouts dumped at the foundation keep garden-level walls wet. The yard is small, and the water has nowhere obvious to go.
Grade is the first plant. Soil sloping into a limestone foundation beats any shrub you add. Even a narrow gangway needs a path for water that is not the neighbor's well. Fence lines on the lot line collect leaves and hold them against brick. If the basement is already damp, say that before you talk about flowers. Hardscape that has heaved is a trip, not a style issue.
The parkway strip is not always yours to redo. Say if the work you want is on that strip or only in the private yard. Replacing a gangway hedge is a width problem. Salt splash reaches farther than the curb. Containers on a masonry stoop are not the same job as rebuilding a yard. Irrigation in this climate has to be blown out before a freeze or it becomes a plumbing call.
Lake wind dries east-facing evergreens and topples a weak new tree. Choose plants for shade, clay, and salt, not for a weekend of mild weather. Mulch piled on the trunk will rot bark that the wind then finishes. Spring is short; fall planting has its own race against a hard freeze. If a limb is on the roof or over the public walk, that comes before a bed plan.
Lead with water at the wall, a heaved walk, a parkway tree, or a limb on the roof. Say whether the gangway is part of the problem. Name the floor of the basement that is already damp. Chicago clay and lake wind do the rest if you wait. Call the number on this page.