Harry is right on target with his range. My personal experience is $30,000 is about where it will end up with all costs and permits.
It is critical to have licensed contractors do the work and be sure you get the necessary permits. The city will also require the lot be fenced as and after the work is done.
I would contact a qualified demolition contractor to get proposals. You should request that the contractor be licensed and insured (both Liability Insurance and Workman's Comp). They should also participate in a C+D (construction and demolition) recycling wasted program. Allied Waste runs a very good facility in the city, and will divert almost all C+D materials from landfills. The added cost is marginal.
I suggest you also look into deconstruction and donating usable materials in the home to an organization such as the Delta Institute. They run a construction materials reuse facility called the Rebuilding Exchange in Brighton Park. Also check out http://www.urbanhabitatchicago.org/. They have deconstruction contractors to refer you to, that can give you proposals. Old homes are filled with fantastic materials we'll never be able to work with again unless we harvest them from existing structures. I'm sure the cost are becoming very competitive, especially if there are tax incentives to donating the reusable materials.
Best of Luck,
Keller Williams CCG