Check to see if you have to install any manholes, fire hydrants, curb, gutter, sidewalks, street signs, street lighting any specific street design or access requirements, Check DOT requirements for access, stop lights and permits, traffic studies, DWQ requirements for permits, permit fees and time frames.Once you have an idea of what you can build and what is required in terms of permitting and infrastructure you want to talk to some civil engineers, architects and commercial general contractors that do the type of projects and build the type of buildings you want to build so you can get an idea of costs, time frame and requirements.

Call the landscape architect who worked with the subdivision design company.

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I would consult an architect or structural engineer.  

@Kumud Shrestha Some of the best ways to find contractors is to talk to architects, designers, engineers, realtors and other investors.

I'm an architect and my husband works for a general contractor, and it has always been our dream to invest in Chicago AND build new here.

The builder is on board and my architect is working on the plans.

I was looking for recommendations as far as architect's or a draftsman to help me make this plan possible.

If anything, this is the perfect time to switch Architects before submission and the current Architect becomes the Architect-of-Record with the City.

FYI: If you call an architect or GC and tell them you have this "brilliant never before considered" idea of turning offices into apartments, the architect will eye-roll so hard that they risk permanent blindness.