I have been planning on this for almost two years moving to Chicago. NYC has become too sterile for me, as if people are nothing more but the shadows of what they have used to be, and it is just too much for my artistic soul. Which neighborhood would you recommend? For now, money is not the problem.
You havent told me are you going to buy some place, or just rent? Anyway, Chicago does have a lot of different areas and you should be well acquainted with all of them so that you could choose wisely. I would go for Lakeview or Lincoln Park. I know these are most expensive areas, but you have said that it is not the problem. Still, until you see the areas, you will not be able to decide.