Actually, I am planning on going this year with my wife. I did it a couple of years ago on my Prologue, not sure what bike I will bring this time. We have family commitments bringing us to Illinois, so I figure I would get a ride in or two.
FWIW: I did this ride a couple of years ago. I was really worried about parking. It is not a problem! I parked about 3 blocks away at a pay lot. I should have just parked on the street. As I recall, you would have to feed the meters after 3 hours or so, but being 3 blocks from the start, and the route being a loop, I don't see a problem taking a slight side trip on one lap, feeding the meter, and back into the ride.