Santander wrote:Late July isn't really the time to be planting anything
You can still grow some herbs and vegetables for fall harvest. You might want to give cool-weather crops some protection from the sun and extra watering.
Planting Vegetables in Midsummer for Fall HarvestAlso, many perennials, garlic, flower bulbs, trees and shrubs do well with fall planting.
Santander wrote:Other planting recommendations are also welcome. If you were starting from scratch, what would you consider planting in your first year, both around a house's perimeter, and perhaps in a newly-turned garden plot at the far end of the yard?
If you want fruit trees, start early, because it takes a while before you get fruit. Ditto asparagus.
Fruit that does well in Chicagoland include apples, pears, cherries, plums and peaches, but they need attention. For lower maintenance, try currants, raspberries and mulberries. (If you're not vigilant, you may get mulberries whatever you do. I find them rather tasteless and would rather get rid of them, but they're hard to eradicate.)
We also have a fig, but it doesn't always yield a crop.
Choose varieties suitable for Zone 5 or colder.