wouldn't doubt the above pic was taken in sheboygan, wisconsin. They're situated on a point in the middle of the lake that gets swells from all angles, plus they have an excellent jetty/wind break (not unlike manasquan or sebastian inlets).
idk, Chicago is on the south corner of the lake, so although they could possibly get a much larger fetch from the north, the swell window is extremely limited. I'm guessing ridable surf there is rare and extremely short period/junky. Depending on the length of your visit, the chances of you scoring clean is probably minimal. I haven't heard of chicago even having decent sandbar and reef setups like sheboygan....but if you're doing it just to say you did it, have at it.

