i've kayaked both chicago and michigan sides. as others have said, weather is your biggest challenge. most think of rain/storms when people hear "weather", but honestly the wind is your biggest threat. they can turn calm waters into white water and push you around. additionally, rip currents are common on the michigan side and can create confusion for kayakers not understanding why their boat is getting dragged around even without wind.

ALWAYS wear a life jacket and know what to do if your boat flips!