Appleton? Hmm...not an area of the state I'm overly familiar with (hopefully someone from around there pipes in). If I were in the area, I'd consider riding around Lake Winnebago ( http://www.midwestsportsevents.com/m...MapFinal09.pdf ).
But, if you're driving from Chicago to Appleton, I'd suggest taking the long route and going via Madison, in particular, Mt. Horeb and ride the proposed 2012 (?) Olympic Bike course ( http://www.tourofamericasdairyland.c...escription.php ). I'd start with the Uphill Grind for bike rentals ( http://uphillgrind.net/ ).
Any ride west of Madison is going to be worth it -- rolling hills, low traffic roads and great scenery. Some consider it some of the best riding in the country. I'm not sure about that, but it is the best riding in the midwest.
Now, as for Chicago--nope, too big of city; too much traffic; too busy for this woman. I try very hard to stay away. You might try posting your question to the Great Lakes form on Bike Forums (http://www.bikeforums.net/forumdisplay.php?f=233 ) Unlike some of the groups on bike forums, the guys on the great lakes forum are well behaved. Most of the regulars are from the Chicago area (even if they do talk about riding in southwest Wisconsin more than Chicago!)



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