Our lawn was a complete mess when we got it and was full of dead grass when we bought it a few years ago. We are up here in Minnesota so a little colder than Chicago land but similar climate/ Here is what we have done to upgrade it to more "no lawn". First off is mow less and remove all fertilizers which I assume you have already done. We have been putting down tons of White Dutch Clover in both the early spring and fall which has just started to bloom this year. We have also been putting down Self Heal and Creeping Thyme which we got from Flawn which we put down over the winter. Not sure what is coming up from that yet. We are going to do their English Daisy in our side lawn.

We have been more focused on our garden which we are planting both natives, edibles and medicinal perennial plants. That has been bringing in bees and other valuable plants. I would recommend Prairie Moon for natives for both research and to purchase seeds. We cut down some trees between our fence and alleyway and put down native last fall. We got some blooms this year but most won't come until next year. The whole thing is a process since we are dealing growing things. The goal is a stable ecosystem which means things will change every year with plants coming and going as their niches get filled and created.