If you do sail to Chicago I have family there that could give you some ground support.
Is Resolute the same mighty Pearson 27?
Considering the outrageous cost of trucking and the depressed market for older boats it would probably be far more economical to sell Resolute where she sits and buy something else on the west coast. Trucking her 2000 miles is gonna be big bucks.
If you do sail to Chicago send me an email: systormalong......at......yahoo.......com.
My brother, who owns a Tartan 33 can help you with boatyard arrangements.
Nell and I are living in Langley, WA, on Whidbey Island, a short ferry ride away from Port Townsend.