Hmm, my cousins in Windsor aren’t so far away.

You could head east on US 36 across KS/MO, lotta 4-lane road there.  Then jump up to US-24 across IL and IN. Some 4 lane road there.  You would have get around Peoria, IL.  Once in IN cut up north somehow, I am not as familiar.  

I hauled a bean head around Indianapolis on a head trailer on 465 last month because there wasn’t any other good way to get east to west.  Didn’t like it, saw multiple cops, no problem.