The conditions can be extremely dangerous for even the strongest swimmers.
Thursday night at 63rd Street Beach, a kite boarder was out enjoying the gusty winds and choppy waves.
But for many along the lake, this certainly wasn't beach weather.
"It was really windy. I mean, it's nice and peaceful because no one's here," Ann Hanke said.
With wind gusts of up to 40 miles per hour expected Friday. We could see a repeat of a scene from last fall when joggers and bicyclists proved no match for powerful waves.
With expected waves Friday as high as 21 feet, the Coast Guard has a warning for boaters.
"You want to make sure the vessel that you're going to be on is appropriate for that type of a sea state. And to be quite honest with you, not many vessels out here are equipped to handle those kinds of seas," said the Coast Guard's James Strempel.
It certainly won't be boat racing weather, which is why organizers of the 20th annual Verve Cup Regatta, sponsored by The Chicago Yacht Club, will likely have to cancel day one on Friday of the three-day event.
"This is a recreational sport," Verve Cup Regatta Chair Martin Sandoval. "There's always the competitive adrenaline in everyone, but safety comes first."
There's also the threat of water spouts, tornadoes on the water, like one spotted last fall on Lake Michigan.
Meteorologist Chris Bedford, who has forecasted for the America's Cup and other races, has this advice for boaters.
"I would definitely not be out (Friday)," he said. "It's not worth it. For one thing, it will not be enjoyable out there. I think if you want to have an enjoyable day on the water, you just want to look at it from the shore."
As of Thursday night, Chicago's Office of Emergency Management and the Park District are not necessarily advising people to avoid the lakefront or Lake Shore Drive, but officials say they will be monitoring conditions throughout the day.