Join Date: Jan 2010
Location: Southwest Michigan
Bikes: Fuji touring bike
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I use the UniversalMaps to get across Indiana and Ohio. I've never ridden further east than that. Actually, in Ohio I often use the Puetz county maps, too. But they are no longer in print and would add bulk to your load.
The UniversalMaps don't tell you which roads are paved and which are not, but in Ohio most are paved. In Indiana one can guess.
The Illinois Department of Transportation has excellent bicycling maps online. I haven't used them in Chicago, but have used them to places just outside the metropolitan area.
Northwest Indiana can be tricky. A few years ago after a ride that took me from Valparaiso to Crown Point and then into Illinois, I said I wouldn't do it again without better maps. But BikeMichigana.org has posted links to a relatively new bicycle map of the area which I haven't yet used.