I rode the LATE in 2002 (I believe), but didn't like the fact that I had to basically walk my bike for the first 5 miles due to the congestion of all those riders. I hope they changed how they do the send-offs since then, but maybe it's better if you're in the first wave - we were in the third or forth. However, that last 10 miles, along Foster and the lake-front path was pretty enjoyable, watching the sun come up over Lake Michigan.
It is definitely something to experience at least one time in life though.