When you say you are "in Chicago," I assume you mean in the city. I would check with the City to see what their policy is on planting in the parkway; there may be an ordinance against it. If it is allowed, they may have resources to help, or may direct you to properties with planted parkways.

Our city encourages what we call "boulevard gardens" as a way to decrease water use in the summer. To be legal and to preserve sightlines for drivers, the plantings must be kept under 2ft.

I have removed my lawn and planted to the curb (on a court without sidewalk) with native species. Short grasses that tolerate dry soil and full sun include blue grama (Bouteloua gracilis), side oats grama (Bouteloua curtipendula) sand dropseed and June Grass (Koeleria). Flowers include Mexican hat(Ratibida columnifera), liatrus cylindracea, pussytoes, short beardtongues and opuntia.

Around the corner, a neighbour has a wonderful scree garden with various sizes of gravel and an amazing variety of sedums on her boulevard. Another nearby garden is done with low groundcovers like thyme and small boulders. The "Stepables" line of groundcovers would work.

Here is a link that might be useful: Stepables