CHICAGO — For five straight years, Dan O’Conor has jumped into Lake Michigan every single day — no matter the season, the temperature, or the weather conditions.
The 57-year-old Chicago native, who has earned the nickname “Great Lake Jumper,” is marking this unique milestone with a celebratory event Saturday at his favorite spot: Montrose Harbor.
Daily Dives Born From a Hangover
O’Conor’s plunge habit began on June 13, 2020, during the height of the COVID-19 pandemic. Depressed after concerts were canceled and struggling with excessive drinking, he followed his wife’s suggestion to get some fresh air — and leapt into Lake Michigan.
What started as a hangover cure became a daily ritual of healing and personal transformation.
“You breathe and jump,” said O’Conor. “The lake is a wonderful elixir. There’s a renewal, an endorphin rush — it lights you up.”
From Local Curiosity to Chicago Icon
O’Conor’s consistent dives have drawn attention across the city and beyond. With his handlebar mustache, laid-back personality, and concert-loving spirit, the father of three has become a beloved figure at Montrose Harbor.
Despite frostbite and icy winters — including chipping away ice with a shovel to maintain access — he never stopped. He’s now jumped into all five Great Lakes, the Fox River, Lake Geneva, the Potomac, and Pittsburgh’s rivers.
Celebration This Weekend at Montrose Harbor
To commemorate five years, O’Conor is throwing a free public event Saturday at 10 a.m. at 295 W. Montrose Harbor Drive. The celebration will include:
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Live music
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Popcorn machine
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Public plunge access into the lake
He continues to film and post each jump online, often dedicating them to artists like Jimmy Buffett or Chicago musicians like Mavis Staples.
Music, Grief, and Community
A former music industry worker turned wine distributor, O’Conor surrounds himself with tunes and has seen his lakeside ritual evolve into a tight-knit community. Friends and strangers gather to swim, celebrate birthdays, and even fish submerged Divvy bikes out of the lake.
He’s found purpose again — and a new way to process grief, including the loss of his mother last year.
“When you jump in the lake, especially in the winter, you just feel so alive,” he said. “The core reason — that splash, that exuberance — it’s almost childlike.”
Have you ever found healing in Lake Michigan or a similar daily ritual? Share your story or thoughts with us at ChicagoSuburbanFamily.com — your voice matters.
