Race to Mackinac 2026: Chicago's iconic sailing race gets underway

CHICAGO - The wind is up, the sails are ready, and one of Chicago's most storied summer traditions is underway. 

The 117th Chicago Yacht Club Race to Mackinac presented by Wintrust launched on Friday with the Cruising Division departing for Mackinac Island, Michigan at 3 p.m.

The Racing Division is scheduled to set sail at 11 a.m. Saturday. 

The backstory:

Hundreds of sailors from across the country have gathered in Chicago, preparing to take on the largest annual offshore sailboat race in the world. 

During the 290-nautical-mile (333-mile) journey, they'll test their skill, strategy, and endurance against the unpredictable conditions of Lake Michigan.

The Race to Mackinac has long been the Chicago Yacht Club's marquee sailing event, where generations of tradition meet fierce competition.

"I think it really says something about the city. I hope it's something the whole city can be proud of," said Kevin Foote, race chair for the 2026 Race to Mackinac. 

Better known simply as "The Mac," the race brings experienced sailors and newcomers together for a cherished summertime ritual. 

"Everybody on these boats has their role; some people play multiple roles. Some people shift around. As far as the skill, anybody can really do this — it takes a certain dedication, a certain commitment to learn," Foote said. 

Teri Casem and Todd Nugent are sailing "Sunshine Daydream" — and checking this adventure off their bucket list. 

"I looked at him and said, ‘Hey, want to do The Mac?’ And he said, ‘What the heck!’ We had no idea what we were getting into," said Teri Casem, who is participating in the race for the first time. 

Getting to the starting line takes weeks of training and careful preparation — a milestone competitors often call the "first finish line." 

"We're not one of these fancy, modern race boats. We're a comfort cruiser, so actually we can bring a lot," said Todd Nugent, who is sailing alongside Casem. 

Every inch of space counts, as their six-person crew packs food, water, and supplies for a journey that can last up to 60 hours.

"You have to be able to fix just about anything on the fly," Casem said. 

This year, Foote isn't only overseeing the event — he's also competing and says one item tops every crew's checklist.

"The foremost thing is safety gear," Foote explained. "We are going to be crossing the lake, you are going to be out there for as you mentioned, 289-nautical miles; there are times when you are just on your own."

For many crews, simply reaching Mackinac Island is an accomplishment in itself, with the memories lasting far longer than the final standings. 

"To be able to accomplish that is going to be just so satisfying," Casem said. 

This year's race features 44 boats in the Cruising Division and 208 in the Racing Division.

What's next:

The Racing Division will launch near Navy Pier beginning at 11 a.m. Saturday.

If you can't catch the start in person, you can follow the entire race in real time on the Chicago Yacht Club's online race tracker.

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