For you to visit the ladies?  
I'm wondering what area is best for YOU.  
Magnificent Mile , Gold Coast, Downtown?
How about the suburbs?  
O'Hare, Oakbrook,Rosemont, Shamburg?

The O'Hare I-90 corridor (Schaumburg, Hoffman Estates) seems to be best

For me Oakbrook and Schaumburg are better than say O'Hare/Rosemont. Easier parking.  I don't get into the city that often as it is a hike and time commitment.

Or O'hare, is close for business travelers or layovers.  Oak Brook/Lombard area is not too bad either.
Schaumburg caters to those who live in Wisconsin, and Iowa.
lol....just kidding.  
But for cruise night the 27th, it is DT for sure. ;-