Retiree Embarks on Winter Journey from Chicago’s Navy Pier

Matt Jonkman, a 52-year-old retiree, has set sail south from his home near Navy Pier in Chicago, seeking warmer waters as winter approaches. Since April, Jonkman has lived aboard a 50-foot catamaran anchored just off the breakwater, accompanied by his feline companion, Monty. With plans to return to Chicago’s waterfront by spring, Jonkman embraces this unconventional lifestyle, finding joy in the adventure it brings.

Jonkman describes himself as “very much happy” with his life on the water. His houseboat, equipped with modern comforts such as a kitchen and a lounge area, offers an appealing alternative to traditional living spaces. He has become somewhat of a local fixture, often spotted waving to passersby. “I always wave at that man, and he always waves back,” said Karina Zuniga, a tour boat captain who has observed him from her vessel.

Public Harbor Living

Living in the public harbor has allowed Jonkman to avoid steep docking fees commonly associated with private marinas. He occasionally rents a dock for short periods to access amenities like mail and groceries. Despite the challenges of life on the water, including weather-related hazards, Jonkman finds the experience rewarding. “Thirty percent of the time you’re trying to stay alive,” he remarked, referencing the need to maintain equipment and monitor conditions.

Originally from Indiana, Jonkman’s journey to this lifestyle has been shaped by personal and professional experiences. A cybersecurity expert, he previously built a successful company and has spent significant time pursuing hobbies such as flying. A near-fatal plane crash in 2020 changed his perspective on life, prompting him to seek a simpler, more self-sufficient existence. “The accident made me slow down,” he said, reflecting on how his priorities shifted after recovering from the incident.

Building Connections and New Beginnings

Jonkman’s daughter, Savannah, expressed a mix of concern and understanding about her father’s choice to live on a boat. “He seems happier being so self-sufficient,” she noted, observing a newfound confidence in him. As he continues to adapt to this lifestyle, Jonkman has embraced the community of fellow boaters and the connections made along the way.

Occasionally, he takes calls from business contacts while anchored, showing that his professional life has not entirely evaporated. Jonkman acknowledges that the boat has made him more appealing to potential romantic interests as well. “Everyone is happy to go out on the water for a day,” he said, but added that longer journeys often require a different level of commitment.

While Jonkman enjoys the solitude and adventure, he recognizes that living on a boat in Chicago can be challenging due to limited docking options. Mike McElroy, president of the Chicago Harbor Safety Committee, commented on the difficulties faced by liveaboards in the city. “Chicago just isn’t really set up for it,” he stated, highlighting the treacherous conditions boaters often encounter.

As Jonkman navigates his way through life on the water, he reflects on his journey and the unpredictability that comes with it. “I feel more settled now than ever,” he concluded, even as he admits uncertainty about his future. With a spirit of adventure and resilience, Jonkman continues to embrace life aboard his floating home.