I'm looking for these places anywhere in the midwest, but preferably as close to Chicago as possible.
COASTAL ROAD
I'm looking for a coastal road, something with water nearly touching the road. So, preferably very little land, with no obstructions, between the road and the water. This is my best find so far, "The Great River Road" which follows the Mississippi, and sometimes other rivers, through the midwest. The picture below is near St Louis. If there's a location like this, closer to Chicago, that would would be better.
HUGE, WIDE, WOODEN, DOCK
We may be able to convince them to nix looking for wood, and simply add it in. I've suggested Navy Pier and The Columbian Yacht club in Chicago. The man in the image can give you an idea of the width they're looking at. FYI, it has to support a lot of weight.