I would venture to say cruising IN to chicago from bollingbrook(i think is where we met last time) would still be a great overall idea. This time I plan taking the whole day off from work/anything else that needs my attention and just hanging out with everyone.

Would you want to go grab food later in the cruise? Preferably at a place that has enough parking for around 15 Xfires hahahah.
Last time it was a blast, and we literally stopped everyone where we went, and instead of paying attention to the skyline like normal tourists they all looked at us like candy. Loved every minute of it.

I do want to make sure the weather is a nice 65 to 75 degrees though, so we don't have to worry about being cold and whatnot. I know some of the regulars from last time would love to have the top down in their convertibles. That didn't stop FP from going convertible even in 50degree weather last time lol