Wow Steve,,,now "that" would be a challenge for you all!! :-) LOL...about the Raider riders!! :-) At least you know you'd get a lot of breaks!!
Mileage from there to Greeneville, TN is about 1000 miles, depending on how you come down. If I were on the cycle, I'd avoid most of the tolls in Chicago by taking I-39 down to Bloomington, IL and going East from there to Indianapolis. Going that way however, adds about 75 miles to your trip, however, it saves time by avoiding the numerous toll booth stops. Doing that puts you at the 1050 mile mark for the one way trip. Definitely an Iron Butt ride for whomever would try it. The good thing is that it's all Interstate down here until you get to about Corbin, KY. Then you get the advantage of one of the most beautiful rides in the area through Southern KY and NE Tennessee, across the Cumberland Gap and those lower level mountains. Definitely a ride you'd want to do in the daylight, especially due to animals, but great roads. If you left at the crack of dawn on Friday a.m., you likely wouldn't be riding in any darkness whatsoever.
I would suggest maybe getting to Corbin, KY, in the one day, this would leave you approximately 125 miles to go on Saturday the 27th which would allow you plenty of time to sleep in a bit, have a big breakfast, and then get to ride in the daylight from Corbin to Greeneville for the Charter Signing at 1 p.m. EDT.
Doing that would then have you departing, at lets say, 4 p.m., with still about 4 hours of daylight left, so you could make it back to either Corbin, or a little north of there on the Interstate, say London, KY. Get a room for the night, and then make the trip back on Sunday, and voila, you're home! Three day trip....I know,,,easier said than done making a 2200 mile round trip!! I hope you'll have some takers for a good three day weekend of riding!
Sounds like a fun trip! I'm definitely up for it,,,oh,,,wait a minute,,,I'm already here! :-) It would be GREAT if you could bring a contingent from the "Cities"!!
Jerry