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Ride in wisconsin,I've heard from some ppl that ill has only a few miles of trails. Go to wisconsin, go up to kendale they have some nice trails but don't go to the U.P. to many snomobile trails,only atv trails they got are road ones(no fun).
There are several places to ride near Chicago. The Cliff is in Seneca, Fox Valley Off road is in Ottawa, Badlands in Attica, IN and Rock Glen near Rockford.