Sailing LESSONS

Private & Semi-Private Sailing Lessons in Chicago, IL

Looking to learn how to sail on the stunning waters of Lake Michigan? Whether you're a solo explorer or want to bring a friend, Two Brothers Sailing Chicago offers private and semi-private sailing lessons tailored to your schedule and skill level.


Choose from:

  • 2-hour private lesson – starting at $200
  • 4-hour private lesson – starting at $400


Enjoy a personalized, hands-on experience with our expert instructors as you learn to sail in Chicago. Glide past the skyline, feel the wind in your sails, and discover the confidence that comes from taking the helm. No prior experience needed—just a sense of adventure.

A man standing on a sailboat with his arms outstretched
A sailboat is docked at a dock in a harbor.

Corporate & Group Team Building Sailing Events

Strengthen your team with a unique and unforgettable day on the water. Our team-building sailing workshops are designed for groups of up to 50 people and combine learning, collaboration, and a bit of friendly competition.


Your 3-hour sailing experience includes:

  • A 30-minute classroom introduction to sailing fundamentals
  • Guided on-the-water training with experienced captains
  • A thrilling regatta-style race to put your team’s new skills into action


Perfect for corporate retreats, leadership development, or group celebrations, this event fosters communication, trust, and teamwork in an exciting, hands-on environment.