Mike Johnson wrote:
You can go the shoreline. There is one airport north of Chicago (Racine
WI?) whose CDAS extends out into the water, but you can go around it to
the south and then swing north. You can also fly beneath the CBAS
around/over Chicago then north and follow the DuPage River north to the
highway and on to OSH. Clow International used to have a nice restaurant.

It looks like I'd cross Gary CDAS between 3100' and 3600,
below 3000' within 15 nm of ORD, follow shoreline until
greater than 15 nm of ORD, then west of Waukegan or over it
between 3200' and 3600' and on to Oshkosh.

That's right, Racine is farther north. South of Gary and west of
Waukegan will keep you clear of CDAS.

If I wasn't flying the family, I would accompany you in the 1945 7AC
that I fly. Last time I flew it to OSH was 1986. I flew it to Sun N Fun
two years ago. OSH is eight hours and three fuel stops flying time from
Columbus OH. (Huntington IN, Clow IL, Fond du Lac WI)
You will want to land short of OSH for fuel and telephone OSH for
information on when NORDO's will be admitted. They limit the access times.j