Most all of the big boats where I am spend the winter on the hard on a cradle. The cradles are typically stored at the marina during the actual sailing season.
If it had a cradle, you could always buy a bare 14k trailer frame and weld the cradle to it. depending on boat weight, a dual 7k axle trailer might suffice, as long as its not a deck over, then its too tall.
If you have the right tow vehicle and you have sufficient towing experience, even if you buy and outfit a trailer for 8k in chicago, when you get to portland, you still have a trailer. can sell it or keep it or whatever. though i bet you can buy a sufficient boat trailer around Chicago to haul this for a reasonable price.
also, you might be able to rent a trailer for this from a private individual that owns one in portland, and round trip it. Maybe spend $500-1000 to rent it? post up on craigslist/FB or ask the marina yard?
for a $9500 quote...i wouldn't think twice about hauling this myself w/ my 3/4 ton diesel. Lodging...sleep on the boat in a truck stop or something. Cooking, use a 2 burner coleman stove, itll be like camping lol. Have a good job? take vacation time and get paid to haul your boat.