Strictly Sail Chicago
I live an hour away from Navy Pier. I go every year, but I do not think this is a show that is worth a long trip to see. You will see pretty much the same boats you see at all the shows - Catalina, Jeneau, Hunter, Tartan, Caliber. There will be a few unsual makes, but the mojority of the show will be boats you have seen before.
I go because I love to be around boats and sailors and, living nearby, it helps me get through the cold Illinois winter.
If you want to visit Chicago, go to the show. To make a special trip - I say it is not a good enough show to justify the expense.