Chicago pretty much sucks. Stick to the Michigan side of lake Michigan. South Haven, Grand Haven, Muskegan, Traverse City (personal favorite), beautiful marina in Elk Rapids, Charleviox, Petosky, Makinaw area, and the inland waterway from Cheboygan almost all the way to Petosky. Ive done all of those and would be happy to help if you need any info. Havnt been to Beaver Island yet. Traverse City for the air show during Cherry Festival is a blast but real crowded.