My main interest is in doing it solo, I don't think I'd enjoy it nearly as much with other people around. While this does look interesting, it doesn't appeal to me in the same way
I remember reading Robert Manry's Tinkerbelle[1] as a child, and ever since have had something of a fascination with the idea of sailing solo; although at my now-fairly-advanced age I accept that I'm going to keep my ambitions severely in check.
For what it's worth, I sail and the average other sailboat I meet is sailed solo by an older guy. A small to medium coastal cruiser/overnighter type seems to be the sweet spot, can be easier to single-hand than many kinds of dinghy, cheaper and with easier boat handling than big cruisers and less to go wrong. So it may not be Atlantic crossing but I hope you get some sailing in.
Don't know much about Illinois, but there are lakes up there I've heard, surely there are sailing clubs, etc for the summer. I have a small (14 foot) two-hull dinghy thing I bought maybe 38 years ago that I need to get out again on one of the lakes or bays here south of Sydney , Australia.
[1] https://en.wikipedia.org/wiki/Tinkerbelle