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Some times we just have to buck up and grit our teeth and go through cities that we normally want to avoid. Is it worth a diversion out of our way to avoid some temporary grief and how much are we willing to go out of our way is the question I suppose.
Cleveland is no big deal really. Chicago area can be totally unpredictable. Looking at the route I would go straight through on 80/90 then stay on 80 all the way to Omaha and pick up 29 north to 90. Really, once past Chicago its pretty wide open from there.
Along the Missouri River is the Lewis and Clark trail with some interesting stops to be had. We try to get off the E-way and go secondary roads as much as we can and find it more interesting that way.
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