I think it depends largely on what your goals are. If you want to remain small (where I define small to mean 'less than 4 full-timers including yourself'), then it probably doesn't matter much where you are. If you want to grow beyond that, you need to either go where there is a decent-sized talent pool or be in a desirable location. As locations go, Chicago isn't terrible, but the urban centers in California, Texas and Washington probably trump it. It could be worse, though; you could be in Detroit.