Have you thought of the Pacific Coast? It isn't starting from Chicago, but it is scenic for most of it, and it's not logistically impossible to complete it in chunks, as there are transportation options.
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Hi All, This is my first visit to this forum. My wife and I plan to cycle SF to LA and are having problems acquiring accommodation in Big Sur for 31 March, 2017. We are carrying our own gear but not tenting. Can anyone give us some advice.Hi Gordon