Inspired in part by having just heard "The Wreck of the Edmund Fitzgerald" on the radio; Gordon Lightfoot opens with:
"The legend lives on from the Chippewa on down
Of the big lake they called 'Gitche Gumee'
The lake, it is said, never gives up her dead
When the skies of November turn gloomy"
But how much seafaring (lakefaring?) on Lake Superior and the rest did the Chippewa and other tribes in the area actually do?
Lots of paddling but no Sailing
There is significant physical evidence that Native Americans traveled to various islands in the Great Lakes. There are hunting artifacts on Pelee Island and pictographs on Kelley's Island in Lake Erie.
There were Ojibway (Chippewa) recorded as living on Michipicoten Island at the time of first contact by Etienne Brule around 1620, and there were prehistoric copper mines on Isle Royale. Both of these islands are in Superior and are near to the route of the Edmund Fitzgerald. They are both around a dozen miles off the the mainland, which is close enough to be visible, but far enough to make it more than just a lazy afternoon paddle. (And not in a storm, and not in November.)
Later, when the fur trade picked up, the larger loads of furs were transported to Montreal in 30-40 foot canoes, except for the obvious portage at the Niagra River and the rapids near Sault Ste Marie.
Although every paddler learns to adjust course for tailwinds, the first actual sailing ship on the Great Lakes was the Griffin built in Robert Sieur de La Salle in 1679.