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I'm doing it in an RV this year (also my first RAGBRAI)
I'm doing it privately.
if you're interested in a charter service check out RAGBRAI's page for that... and definitely check out their forums. there have been postings for Chicago based groups on there before.
The best way to get to Iowa for RAGBRAI is to find somebody who has room in their car. You only have to get to the finishline and then you can hire somebody like Out of Staters (oosbicycleclub.com) to take you and your bike to the start. You can also pay them to take your luggage each day and provide space in a smaller campground. But RAGBRAI will do that and it's included in your basic fee.
OOS can also pick you up at a nearby airport or train station, I think. Just take a look at their website and contact them for further details. I've used them about 6-7 times and I've always been very satisfied even though the price keeps going up.
It's lots of fun and I'd be happy to show you slides and photos and I can even link you to my website about past Ragbrais
http://www.kangarooconnection.com/Kathy%27s%20Ragbrai%201999%20.html
http://www.kangarooconnection.com/Ragbrai2001.html
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