Family and friends watched as the boats leave the shore near the Chicago Yacht Club and pass Navy Pier.
"It's great weather it's a great event and we just thought we'd come and see all of the boats and knowing we had a horse in the race we wanted to see them head off on their way," said Damla Gerhart.
"It's a labor of love, it really is," said Jim Murphy, aboard Wind Shadow.
And it starts with a lot of preparation.
"Every year it's a different year, different weather conditions you never know what can pop up," said race participant Danny Burleson.
Once on deck, members of the team try and get their head in the game.
"You've got to concentrate a lot for a long time," said race participant Spencer Channell.
But also make sure to have a great time along the way.
"It's strikingly beautiful," Murphy said. "At one point in the race you go into shore up around the Manitaw Islands. You see the dunes it doesn't look like Michigan it looks like you are in paradise."
Some of the boats are expected to reach Mackinac on Monday.