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Chicago Private Boat Charters on Lake Michigan

Find Your PerfectChicago Charter Experience

Private boat charters for small groups on Lake Michigan—sunset sails, fireworks nights, Playpen days, and sailing lessons, all led by licensed captains and tailored to your experience.

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Vagabond sailing yacht under full sail on Lake Michigan with clear blue sky
Lake Michigan - Chicago

  • Curated Fleet

    From premium sailboats to smaller group charters

    Options for intimate, private groups

  • Lake Michigan Sailing

    Chicago skyline, harbors, and Playpen

    Direct access to top on-water destinations

  • Captain-Led Experience

    USCG-licensed captains

    Seamless, private charter experience