Chicago local here, and Lake Michigan kitesurfer and surfer. The best swells hit when in the fall and spring, so you better have a good wetsuit. That said, since getting into the sports it makes me love the lake even more. You quickly get over the temp, and just get to enjoying the water. Its also nice to not have to worry about sharks! Some of the best surfing in the area is up in Sheboygan, WI, the Malibu of the Midwest.
I practically live in Lake Michigan in Chicago, because of my dog, and learning to embrace the cold means you get the beauty of seeing this huge, open expanse of water with nobody else around, because they are sane and are avoiding the cold.
I loved kitesurfing on Lake Michigan before I moved out to the gorge this year. I was out in Indiana and usually rode MC, Lake St and Wolf. I made some great friends and have some awesome memories of my time there.
> You quickly get over the temp, and just get to enjoying the water.
Having grown up in Michigan I'd say it's more aptly put as "if you're one that can learn to live with the temperature the water can be a lot of fun" as certainly not everyone gets over it - even of those that often enjoy the water!
Never really cared much about the lack of sharks but I will say there is something special about having that "I might as well be at the ocean" scale of water without the damn salt.
