I’ve crossed the lake several times, closer to shore you’ll see sailboats and in the middle container ships, there will be a long stream of calm waters behind a container ship for miles long, this helps with spotting them.
The Chicago bravo airspace is difficult to deal with especially if you are flying IFR, you’ll get routed out of the way quite a bit. For VFR if you are flight following ATC will keep asking you to fly lower and lower, if the bravo starts at 3000’ they might want you to be at 2000’ or lower.
Keep in mind that Midway recently changed their class C airspace ring to encompass more of the lakeshore space from 2300’ upwards. We keep getting pushed lower and lower to the ground, might as well fly on Lakeshore Drive.