Good job joe, but I see that Downtown is in the lower left corner. One thing I'd change is that I would have left Downtown Chicago at the mid point of the map right off the middle/right edge of the of the lake shore just like it is in real life to make it feel like the "center of the city" then you can have the beaches and sh*t for the people who think that EVERY f*cking GTA must have a beaches. Rockstar left the skylines of Los Santos and Liberty in a similar place as the real Los Angeles and New York and probably would keep Downtown Chicago in it's original place too.
The anatomy of Downtown Chicago being in the middle of the city is important because there are two important places associated with Downtown, which is the "Gold Coast" and "Magnificent Mile". The Gold Coast is a neighborhood north of the Loop with all the condo apartments right off the beach/lake that is one the top 10 richest neighborhoods in America. Most people in Chicago will never afford to live there, but it'd make a nice for a safehouse once you make a million dollars. And "Magnificent Mile" is a street in Downtown ranked one of the top 10 most expensive retail streets in the nation with all the high end stores like Gucci, Louis Vuitton, Prada, and a bunch of sh*t you cant afford. But those two places really don't work unless they are positioned on the map similar to how they are in real life.