Now that we are both retired, road trips are much more practical.
We drove from Chicago to Columbia, MO (home of the University of Missouri) and stayed in a hotel across the street from a very nice city park (Cosmo Park) that had very good greenswards and nice people. Light overcast before totality, but the disc was clearly visible through eclipse glasses. It seemed to break just in time for totality, which gave a wonderful show (too bad the totality interval on this one was relatively short). Ten minutes or so after totality ended, a typical midwestern dark cloud totally covered the sun (one could not find it even with the naked eye), but there were breaks during the post-totality that allowed visibility through eclipse glasses.