Yeah, we had a group of 3 boats I was on did this trip from St. Joe to Chicago and back on July 4th 1991. Of course back then we didn't have a GPS to help us out, but about half way or less we could easily see the Chicago skyline which made it easy for navigation.
We came back the same day, but the return trip to St. Joe was a little different navigation wise---we were off to the north a little by about 10-15 miles or so. We could tell by the steam of the Palisades Nuclear Plant just south of South Haven.
Having the tech of a GPS will be a whole lot easier these days.