I second the Annapolis suggestion
Go to Annapolis! I've been to Strictly Sail in both Chicago and Miami, the Michigan City show, etc. etc. The U.S. sailboat show in Annapolis is far superior with many boats (Valiant, Hallberg Rassy, Hinckley, Swan, etc.) you won't see at the other shows. The Annapolis show blows all the others away. Plus, you can have dinner at O'Leary's Seafood Restaurant as a bonus.
If you live in Michigan you can get cheap round trip tickets to Balitmore for around $130.00 on NWA out of Detroit Metro any day of the week, rental cars are cheap, and so are decent hotels by the airport. The nice hotels in downtown Annapolis are either booked up or charging $400.00 a night.
You can also spend a day wandering around Jabin's/Port Annapolis and see a wider variety of brokerage boats than you can in a whole summer of shopping around the great lakes.