Chicago - Advice for tearing down and developing a lot
I currently own a pre-fire 3 flat (aka VERY OLD, 100+ years) in a very desirable neighborhood of Chicago and when we purchased it, we purchased it for the land value (tear downs all up and down our block). The house is in good shape for it's age and we did some remodeling to it a year ago and currently live in 1 unit and rent the other 2. Our goal has always been to find a "forever" multi-unit in the city but the more I am thinking about it, the more I am thinking about the possibility of demoing our current 3 flat and building a multiunit, exactly how we want it, on the land. I don't have any experience working with an architect, financing a deal like this, pricing it out or finding the right contractor to do the work who is also familiar with Chicago building codes, expediting permits, etc. This wouldn't be something we do for 5-10 years but want to start exploring if this is realistic and the right plan.
Has anyone gone down this road, specifically in the city of Chicago, who could point me in a direction to start getting some information about what it would really take do to this?